Is Dating a Skill?

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“Just be yourself” is the most common dating advice in the world. It’s also the worst. Men who send dick pics are being themselves. Verbally abusive men are being themselves. Ultimately, dating success isn’t about pretending to be someone you’re not, but rather, about being the most confident, generous, self-aware person you can be.

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  1. 1

    What a great idea, Evan, to create this podcast! Thank you for posting it!

    Dating is definitely a skill – one that I admittedly don’t have, which is why this podcast drew me in.

    I really try my best to be positive about dating – ex., thinking of each date as a new opportunity rather than a retread of previous problems. But the truth is that I’m terrible at dating. I’ve honestly come to dread it because I’ve had enough bad experiences with dating that I don’t view dating as being any fun at all.

    I know that’s a terrible thing to say. And I really don’t mean to be negative. But in all honesty, my experience with dating is that it’s no different than a job interview. I think that’s why I’ve never been able to be myself on dates, which I know is part of my problem.

    On dates I feel like I’m interviewing for a role and having to sell my qualities in order to make the cut. I also feel like I’m being scrutinized for every single thing I say, do, and for how I look. So I act with the reservation and caution such a situation calls for. As a result,  I rarely get second dates. And I’ve never had a date lead to a boyfriend. I’ve cried many tears over this.

    Complicating it for me is that I’m not particularly attractive. I’m 5’8 and 130lbs. I exercise almost every day. And while I don’t have a horn growing out the center of my forehead, on a scale of 1-10, I’d give myself a 3 (with no makeup on). With hair, makeup and the right clothes, that would put me at about a 5. Not ugly, but hardly a head-turner.

    Personality-wise, my friends say I’m the nicest person they’ve ever known. I really do care about people, and I like demonstrating it. I think I have a good sense of humor. But it doesn’t come out unless I’m comfortable enough with the people I’m with to reveal it. I’m often pretty quiet. I can be talkative, but I prefer to listen rather than talk.

    In combination with my academic job and my PhD, I know I can come off as aloof and intense, although I try really hard not to. I am confident, but it’s a really quiet, internal self-confidence that isn’t immediately apparent to people. Showboating, grandstanding, and shameless self promotion is not my thing.

    On dates I rarely talk about my PhD, or that I have a pretty good job. I just say I work in academic administration, and that I’m content with my job. I try instead to ask leading questions to try and get the guy to talk about himself, and to show interest in what he says. But to be honest, I’m always unsure how much of myself I should reveal on dates. Thus, my dates always feature long, awkward pauses.

    I’ll admit that I’m insecure about the fact that I don’t think I have a tremendous amount to offer a guy. I’m not beautiful. I have almost no relationship experience. I’m not particularly outgoing or entertaining. I’ve never been one of the “cool kids” (I was always in study hall!).

    Instead I’m reliable, trustworthy, and conscientious. I try to do what’s right. I have all of the standard hobbies, but I’m not a standout in any of them.  I have a good job, but it’s nothing snazzy. And while I have a doctorate, I don’t believe I’m extremely intelligent. I just had a goal of earning my PhD and I didn’t stop until I’d gotten it.

    Don’t get me wrong – I’m very proud of what I’ve accomplished. But at the same time, I don’t think I’m any more or less remarkable then the next person.

    It’s interesting what we think is successful, and how that transfers over into attracting a partner. I’d say that my biggest success in life has probably been earning my doctorate, because it took ten years of my life to get there and I had to build a lot of important relationships along the way to accomplish it. But I also know that in the realm of romantic relationships, my biggest success thus far – my doctorate – doesn’t help me at all.

    A doctorate says nothing about the kind of partner you will be, or why someone should want to be with you. It’s an academic qualification that hangs on the wall, but it’s no real testament as to the kind of person you really are. And apart from perhaps adding some financial security in terms of being able to get the higher paying jobs that come with having doctorates, a PhD doesn’t really add anything to a relationship. My friends always tell me to emphasize my PhD when on dates. But I don’t, and that’s why.

    Instead, I probably need to develop new skills that are particularly targeted towards success in romantic relationships. Just because I was good enough in one area – ex., academics – doesn’t mean that that transfers into all areas of life. Thus, I would love to hear more about how normal, average, everyday women like myself can develop the skills to date effectively.

    1. 1.1

      I really empathize with you because I was in that same boat–rarely got second dates, introverted, not very experienced with relationships, etc.   (and on the physical attractiveness scale I’m somewhere in the middle.   I neither make people gag nor take their breath away).

      However, now I’m happier than I’ve ever been, with a guy I adore.   If I can do it (while not having anything you don’t), so can you.   First of all, rarely getting second dates is not some obstacle that’s only unique to you.   That’s just dating in general and happens to just about everyone I know.   So one thing to do is to take it less personally (I know, I know, easier said than done but that keeps you going).

      I would also think of dating as more of a two-way street, to take some of the pressure off of you.   The assessment goes in both directions.   Just as a guy is assessing you, you should also be assessing him to see if you’re a good fit for each other.   Rather than only focusing on whether you think the guy likes you, think about whether you like him.   It’s about trying to connect with someone, not them scrutinizing you for mistakes like some Olympic judge!

      At least from what you’ve written here, it sounds like you probably deserve more credit than you give yourself.   I see from your post that you are intelligent, kind, humble and self-aware.   From the horror stories I hear about some demanding, “entitled” women from my guy friends (and my guy about his exes), those are not qualities to take lightly.

      I actually wouldn’t emphasize the PhD too much.   Not to say to hide it per se (and really, good for you for having it!) But I agree with you there that it isn’t the kind of thing that makes you look like a better romantic partner, so I wouldn’t go on and on about it either.   When I dated men with impressive educational and occupational credentials, that made me want to hire them, but not be with them romantically.

      Dating is a bit of an acquired skill.   In the end, I say be yourself, but also learn to bring the best version of yourself to dates.   Once I did that (after lots of dates and missteps), I found love–and am confident you can too.

    2. 1.2

      Hi Marillah-nice post. I certainly don’t have the educational successes you’ve had but I can relate to what you said. I consider myself to painfully shy in the past. I got the “reserved” remark enough I took it to heart and worked on my conversational skills. It’s embarrassing but I really had to push myself. I started making myself talk to whoever was in line with me wherever I was. I started slowly complimenting moms on their kids, older people (usually very receptive) etc. then I conquered my fear of conversing with the opposite sex. I took “enrichment” classes at a local college for fun and to push myself to interact. But be assured, you have much to offer and it has absolutely nothing to do with your degree:)

      1. 1.2.1

        Caroline, you’ve reminded me of the experience I had yesterday when I was having a couple of dresses altered.   I was standing there in one of the dresses,   my knee-high nylons (that I wear under work slacks) and high heels thinking please don’t let anyone come in and see these ugly-as-sin leg coverings that would probably embarrass even my grandmother.   Heard a motorcycle rumble through the parking lot and I said to the tailor (a petite Asian woman) “OMG, he’s not coming here, is he!   ACK!!!” and she laughed and said yes, he was one of her customers.   Sure enough, one of the handsomest men I’ve ever seen walked in right as she was pinning the dress down the back, and without turning around I stuck my arm out and said “Do NOT look at these sexy socks, whatever you do!” He laughed, she laughed, and as she went to get his biker vest I sort of sidled over behind her counter.   No need in him getting an even more eye-bleeding view of “the legs,” and we chatted about his cool bike for the few minutes it took her to come back.

        I was painfully shy and dorky as a child and have worked my entire adult life to get over it.   Humor is a great equalizer.

        Marillah, I’ve wanted to respond to your post because it is a very insightful one, but I’m at work and haven’t had the opportunity to do so yet.   You have a lot to offer, so I hope you can work through the shyness as much as possible.   Talking to strangers will help you do it, and since you’ll probably NEVER see them again, who cares if you come off as <insert adjective>?   It’s good practice for that next date when it might count for something. Hope to see you post more and let us know how you’re doing. 🙂

        1. AllHeart81

          SMC – You’re story about the Biker Guy was so heart warmingly funny. “Do NOT look at these sexy socks, whatever you do!” That’s gold!

      2. 1.2.2

        Marillah, I really hope you take all these comments to heart and know what you have to offer.   I sense you really do have a lot to offer, but just need to tweak your mindset a bit so that you can show that to your dates!

        I totally agree with the advice Caroline and SMC gave, to just practice talking to people in general–not just dates.   Some of the biggest stepping stones for me, in conquering my own shyness, weren’t even dates.   One of them was being able to talk to a really cute guy at a party once, without being tongue-tied…and even getting him to smile and laugh a lot!   I used to think that attractive men like that were way out of my league, so I wouldn’t even bother trying. Once I did that, though, I found that he was a really nice person.   If he hadn’t moved out of state, it could have even turned into something more (and he’s still a good long distance friend).

        Another one was when a really good-looking guy at a Halloween party came up to me and asked me to dance–even though there were younger and far more beautiful women also in attendance.   However, those beautiful young girls were sort of scowling, and standing around in “haughty hottie” poses.   Even as beautiful as they were, those scowls would scare off even the most stalwart men!

        I got his attention just by smiling, dancing with my friends and generally looking like I wouldn’t bite his head off.   It gave me a confidence boost that I could attract a man even over more beautiful women, just by having a friendly demeanor (and even a man who, again, I would normally think of as out of my league, who could presumably attract a more beautiful woman).

        Those little stepping stones really helped.   Then, when I finally did meet the right person, I was able to get and keep him attracted to me.   I’m still not the most gregarious person, but still better than I was.   I know you can do it too!

      3. 1.2.3
        Emily, the original


        Like Caroline, I have been described as “reserved.” Or worse, “stuck up.”

        I am not naturally warm and gregarious. Even when I feel like I am coming off as over doing it, I think it reads as “decently friendly” to other people.

        I have been working on my shyness for years. You wrote that your prefer to listen, and I think that is a good quality. Most people want to be heard and acknowledged. They want to feel like the person they are talking to finds them interesting.

    3. 1.3

      Marillah, I will echo Christine in that, if you’re feeling like it’s a one-way interview, realize instead that it is a two-way interview and that he’s probably as nervous as you are.   And you hold a lot of the cards, if not all of them.

      If that doesn’t work for you, try to adopt the mindset of treating the date for exactly what it is (or should be) – a fun night out with a new friend.   Don’t think of him as possible boyfriend material, just friend material, and see what happens.   That should hopefully take the pressure off of you.

    4. 1.4


      Transperancy and authenticity are both very attractive qualities and you have that in spades! A good man will adore you for it.

    5. 1.5


      I think you should hire Evan. If you are getting first dates that means that men are finding you attractive, you just need help with dating.


      Marillah, have you ever been camping? When you first have the spark that gives the flame light, you have CAN NOT just leave it to itself or the fire will go out. You have to put in work to turn that weak spark into a roaring flame!


      Blowing on it, adding wood, even shielding it from wind with your own body until it is strong enough to sustain itself on its own. If a guy asks you out, that means that he has the spark, you just have to do the work to create the fire of attraction and love.

    6. 1.6

      @ Christine, Caroline, SMC, Emily the Original, KK, and Adrian:

      Thank you all so much for taking the time to read my post and offer such thoughtful replies. It really helped me to hear a bit about the experiences of others, as well as the kind words from everyone!

      I also really appreciate the suggestions about what I can do differently. I made a note of each of them. The next time I have a date, I’ll try some of the tips. Hopefully it’ll make a positive difference!


  2. 2

    Marillah said:

    “Complicating it for me is that I’m not particularly attractive. I’m 5’8 and 130lbs. I exercise almost every day. And while I don’t have a horn growing out the center of my forehead, on a scale of 1-10, I’d give myself a 3 (with no makeup on). With hair, makeup and the right clothes, that would put me at about a 5. Not ugly, but hardly a head-turner.”

    Marillah, you’re ahead of me on the no-makeup scale.   I’d give myself a big fat ONE. But no lucky guy gets to see THAT face until he’s madly in love with me and by then sees the qualities that are important to him rendering the makeup-less face not so bad after all.   (I’ve never once had a guy say OMG, who ARE you?   Which I routinely say to myself every morning in the bathroom mirror pre-makeup.)   Please, please, please stop giving yourself a number because it is subjective to the person doing the looking.   (And we women are notorious for underestimating our looks anyway.)   What’s attractive to the world is confidence.   It doesn’t take a Hollywood starlet to attract a decent man.   Confidence is the name of the game.   Sure, looks count to some degree, but they are not the only factor when determining who is attractive to us.   Confidence in one’s own skin is pretty powerful stuff.

    I’m going to hush because I get to talking and sometimes don’t know when to stop (and today is really busy at the office, too). Suffice it to say that once you’ve gotten ready to leave your house/apt. (hair, makeup, etc.) give one last look in the mirror and say, “Not bad for <insert age.”   Say it every single day.   And if you go out at night, say it then, too.   Say it like you’re complimenting your best friend.   Because you are.   🙂

  3. 3

    I’m curious about the opinions of others on something.


    In Evan’s last podcast titled You Can’t Do The Wrong Thing With The Right Guy, he states that A person who is really attracted to you and desires strongly to be with you will overlook many of your flaws.


    In this podcast, Evan states that, your behavior is one of the main reasons why you don’t get a boyfriend/girlfriend or a second date out of the first date. So we should get feedback from the person who didn’t want a second date to know what we did to cause them to not want to date us (assuming that we thought the date went well).


    Since most of us don’t do the feedback thing, we keep repeating those bad dating behaviors date after date, relationship after relationship.


    This got me to thinking, so does that mean that most of the couples that are together are not together because they are a good fit, but because the bad daters finally met someone who was willing to tolerate those bad behaviors?


    In the last podcast titled Are you overestimating yourself, we know that many people think they are a great catch when in truthfulness we aren’t that great, yet almost every person who has overestimated themselves, and who has never learned to stop their bad dating behavior, still has found lasting relationships.


    This has all led me to wondering if most of the fights that even happy couples have, are because though they are a fit, they still never learned how bad of a partner they are because the person they are with overlooked all their flaws, and now the newness has worn off   5 years into the relationship.


    How wonderful would relationships and marriages truly be if we dated someone who really was skilled at being a good boyfriend or girlfriend instead of someone whom we are just so attracted to that we don’t notice their bad relationship skills until we are so invested into the relationship that we hang on because we don’t want the previous 5 or more years to all be a waste?


    Do dating skills or lack there of, transfer to the skills of a strengthening or ruining a good long term relationship?

    1. 3.1

      IMHO, most folks are able to see and embrace a skill when they are exposed to it. In other words, one may be lacking in dating skills but then dates someone who has acquired those skills. It’s similar to how one goes about an unsatisfactory retail transaction. Fuming and fussing at a clerk just creates animosity. While you may get satisfaction through a manager; I’m not sure it affects a poorly skilled clerk positively. Anger just begets more anger. But if you present your problem with the product or service with an attitude of what can be done about this; the clerk will usually respond positively or get soneone in authority who can act on the problem.

      When I first started dating after my divorce; I came across men who just kinda “poofed” /disappeared. About 3 months into dating my guy I was in a predicament where I was unhappy with the overall status quo of our relationship. Instead of tackling the problem head on I just started to fade out. Very poor on my part. Luckily, my guy had much more integrity and called me on it. We talked about it and frankly that simple act skyrocketed his value as boyfriend in my eyes:)


      1. 3.1.1

        And of course, made me respond with integrity to him in the future.

    2. 3.2


      The ‘bad daters’ aren’t necessarily ‘bad’.   They are just bad to the people they go out with because the flaws (whether physical or mental) seen by the other person may be perceived as intolerable.   However, that doesn’t mean that those flaws are intolerable to others and they may sometimes be subjective.   It could be simple as ‘he doesnt chew with his mouth closed’….But let’s remember that not getting a second date doesn’t necessarily mean the other person saw flaws either (especially if talking about online dating). I read this blog once where the guy said he didn’t ask the girl out for a second date because she seemed to have ‘mannerisms that reminded him of his mother’…not necessarily a flaw to someone else.   Another guy said she ‘looked different in the light’ when speaking of not asking another woman out for the second time.

      But I think most second dates dont happen because the man or woman doesn’t feel enough ‘chemistry’ with the other person in terms of either conversation or physical attraction.   And I think that no matter what the other person does, the interest could not be forced.

      But I do agree that there are some people who are bad daters. We’ve all heard of the man or woman that only talks about themselves for the entire date or the ones who dont talk at all or the guy who made a universally inappropriate sexual comment or shows racial prejudice, etc. I think those types of things can be taught.

      So I THINK what Evan is saying is, when you find someone who is really ‘feeling’ you immensely (mentally, physically) and the compatibility is strong, the flaws you exhibit (but let’s remember, we’re talking about ‘reasonable’ flaws and not issues like, I dont know, he likes to kill people on the side or he is a child molester), that we all have (yes, we ALL have flaws) won’t be a dealbreaker in the grand scheme of things because your good qualities will still show you up as a prize to that person.

      1. 3.2.1

        Stacy and Caroline,


        Thanks for mentioning conversation as also  being chemistry, I think that we focus so much on looks that we forget that chemistry has many layers.


        I’m curious of your opinions, with all things being equal and both parties looking like their pictures,


        > What are the main reasons you believe women don’t give men second dates?


        > What are the main reasons you believe men don’t give women second dates?


        > How can (in your opinion) two people be on the same date and yet one walks away feeling this was the best date of their life, and the other person feeling like their was no chemistry?

        1. KK

          Hi Adrian,

          I know the question wasn’t addressed to me, but I’ll throw in my 2 cents anyway. 😃

          “What are the main reasons you believe women don’t give men second dates?”

          I believe the reasons are many and quite varied, but it comes down to feeling like the man isn’t your equal in some way (standards) or just isn’t a good match (extreme differences in beliefs, lifestyle, etc).

          You can see a picture of someone and find them attractive, but you really can’t decide if you’re attracted or not (solely physical) until you meet in person. All kinds of things like how he carries himself, voice, tone, inflections, mannerisms, eye contact, etc, play into the overall physical attraction. Then, you have overall attraction where things like good conversation, manners, and confidence come into play. If any of those things don’t mesh well, it can cause a woman to be ‘turned off’ and result in no second date.

        2. Stacy


          Trust me. I have turned down second dates of very handsome men before. Looks/physical attraction is just the start…one has to be able to have other substantial qualities to back up the looks. What’s the use of having a gorgeous man at my side if he bores me to death or who is really self absorbed  for instance   (yes, this has happened a time or two)?

          But to address your questions?

          ‘What are the main reasons you believe women don’t give men second dates?’

          -usually because it boils down to something the man said. Also, you can find that someone looked like his picture, but there is something about his ‘way’ that turned you off. For instance, I went out with this guy probably almost a year ago when I was still online. The guy looked exactly like his picture but in person (dont flame me too much), he came off extremely feminine in his mannerisms.   He also went into a bit of detail into what happened at a bachelor’s party he went to the night before. I was SO turned off but of course, I was still pleasant. I turned down the second date.

          I think men do this for the same reasons.

          Evan talked about someone asking about feedback…eh…would I really have helped that guy if I told him I thought he had feminine mannerisms? Probably not. And, I wouldnt hurt someone’s feelings like that anyway. After all, it’s not as if he could help it. So, I wonder how truthful the feedback would be in general.

        3. Adrian


          You know I love hearing your opinions (^_^).  Which is why I would also like your answer to the 2nd and 3rd question.


          The second question may seem like it should be asked of men, but I love understanding the how and why of women’s views of men’s actions.

        4. KK

          Hi again Adrian,

          Okay, you got it! 😀
          “What are the main reasons you believe men don’t give women second dates?”

          I think they are similar to women’s reasons with maybe more emphasis on the physical attraction. Since you are a man, correct me if I’m wrong, but I would guess if the physical attraction is there, but a woman has negative qualities (real or perceived) that would result in no second date. Things like bragging about work/accomplishments, using the phrase, “I’m a strong, independent woman”, sharing too much personal information, bad manners (loud, rude, cursing), appearing cold and indifferent, lacking femininity, I could go on… Lol.

          “How can (in your opinion) two people be on the same date and yet one walks away feeling this was the best date of their life, and the other person feeling like their was no chemistry?”

          That’s a good question but it boils down to one of three basic things, I think. Either one person is a little clueless on social cues, when it’s clear the other person isn’t interested OR The desire to be polite can hide true feelings OR (Usually the man) might actually be attracted to the woman and enjoy her company in the moment, but later, upon further reflection, he just isn’t excited to see her again.

        5. Caroline

          I have a pretty similar and much varied reasons for there not being attraction enough fir a second date. The only thing I have to add (it happened a handful of times) is where I thought we had a great date; but he didn’t ask for a second. I pretty much would chalk it up to a nice surprise if a guy pretty much didnt ask for a second date at the end of the first/or coffee/cocktail meet. It happened a handful if times where the guy contacted me a month later claiming he should have dated me but he was wrapped up in dating the available ladies online. I had what I thought was a great date; he walked me to my car at the end of three hours of wonderful back and forth chatting and kissed me. After he walked off and I started my car he literally ran back and asked my last name and telephone number saying he’d call the next day and see what we could plan for the weekend. I never heard from him until a month later. I seriously was wondering how bad a kisser I was! Ha. He contacted me a month or so later telling me he had been dating many ladies online but he realized he wanted to see me. He gave me some lines about women not being what they appeared to be in their profiles. If I hadn’t met the guy I’m dating now I might have gone out with him again. Who knows what was really up but I do think you can get bogged down trying on a plethora of folks aimlessly. Oh well

  4. 4


    Why do you attract me so? I can’t help but be drawn to responding to you although I think you are quite ummm… special.

    Casual sexual encounters go against the very nature of a woman.   SOME women prefer these types of arrangements but when you dig deeper, I guarantee that there is a fundamental (mostly negative) reason for it (unlike men).   Want to prove my point? I guarantee you that if you ask a woman out on a date and especially if she has  something going for herself and you bring up that you are interested in just casual sex, 9 times out of 10, you will get turned  down.   Lots of women go into this arrangement because they are hoping  for something more. Now, with that being said,  if an attractive woman asks you out on a date and  let’s say for the sake of argument that you know she has no diseases/is clean, 9 times out of 10 (If we’re being honest), you won’t turn her down. And this is why, many times, this type of arrangement involves some type of deceit by the man (no matter how subtle).

    So yes, men and women are different in this regard. But that’s why I think I heard Karmic Equation say and I agree, that women are the gatekeepers of sex and men are the gatekeepers of relationships.

    Personally, I could NEVER deal with casual sex.   It would cheapen the experience for me. Plus, I am such a good lay and would never waste it on a one night

    No seriously, it’s because I know my worth.   And yes, I think many women who settle for this arrangement either just got out of a (mostly traumatic) relationship and are going through a phase or simply dont know their value. Casual sex cheapens the woman because of how it tends to make her feel afterward. So, there is nothing in it for her. Plus, let’s face it, casual sex is ‘easy’ for us. We can walk down the street and get it anytime.   So why would it be so fulfilling?




    1. 4.1

      This discussion is moot without agreeing on a definition of “casual sex”. Having an affair with a high-profile man to elevate one’s status is NOT engaging in casual sex, its using sex to get something. Casual sex, imo, should be defined as a type of arrangement where a woman literally gets nothing out of it (except for the actual sex itself of course). And on that I completely agree with Stacy #1 – women who engage in it are dealing with some emotional issues (temporary or permanent) because it IS against the nature of women.

    2. 4.2


      I love your scientific approach. Women and men, respectively,  certainly have hard wired sexual strategies that are employed instinctively. You have given an account of several of these strategies or motivations for women. I’d just like to add that men  know of them from their own experiences. Women have had one night stands with us. Married women have been unfaithful with us. Our most physically attractive male friends have told us that they have been asked  many times by single or married women to have  sex with them without dating rituals. We  certainly know from experience that if a woman really finds a man attractive she won’t care about the dating gospel that is discussed on this site. She simply wants the object of her desire!

  5. 5

    Thank you for this, I have a first date tonight I’m really excited about and this made me aware of how I come across as a date as well. Although since moving to my new city and being happier in general, I’ve noticed an uptick in multiple dates from the same guys, I haven’t found a relationship here yet but have gotten closer than I have before in A very long time.

    A part I struggle with is being introverted and at times a bit shy, I have no problem making great conversation and having a good time, but I’m not the girl to reach out and maybe do the extras to let a guy know for sure I’m interested. I sense I’m probably not a great flirt to men I don’t know well. I’m trying to get better at this and gain a bit more confidence. This is also a reason I’ll accept a second date from someone who I enjoyed but maybe didn’t feel too much excitement for as I assume men feel a bit awkward on first dates as well and maybe more themselves on a second date. Thanks to Evans advice I’ve gotten better at dating and keeping expectations in check, and most importantly, letting men lead. Although I’ve still weathered some disappointments and gotten hurt, I enjoy dating and the prospect of meeting someone special a lot more than I did before.

    1. 5.1



      I wish you well on your date, and I’m glad that you have decided not to give up on dating (I remember a few post ago, you were saying that you wanted to take a break).


      My advice would  is to be warm and friendly, seem like you are really enjoying the date (only if you really are), that should be enough work without having to openly flirt. Guys who are really into you only need the littlest of encouragements…


      When I see a woman leaning in, genuinely laughing at my jokes, smiling at me while holding eye contact, having a dialog with me and not just giving one sentence answers, then I always assume she enjoyed me and the date.


      As a side note (this is personal, so don’t assume this is all men): I like when a woman doesn’t give me the look of awkwardness on a date, like I can’t believe you said or did that. About 7 times out of 10, I make more than most of my dates, plus I know it’s my job to get the bill; but I hate when the waiter drops the bill and the women looks at me, and though it only last for a fraction of a second, it irritates me. The look feels like a test, to see if I am going to pay. I  go on dates to have fun, not to be tested.


      I  agree with Evan about the fake reach, but if you do that and he ends up letting you pay for the entire meal, there you go, you have your answer. He tested you, and  by doing that, giving you a test, he has failed your test. The way I worded that sounds weird and hypocritical, but you know what I mean. (^_^)


      And like many women on here have stated, if you don’t want a second date, insist on paying for your half.


      I feel the same way with any awkward look. If he says something you don’t like, address it then and their but not in a serious or judgmental tone (unless it is really crazy). I have been on dates and told jokes that she didn’t get or misunderstood, the awkward look or stare always kills the mood, verses the women who ask me to explain or play it off.  Remember, we guys are just talking about all these things to impress you.


      This also applies to guys who talk about themselves too much. I would prefer if a women brought this to my attention, rather than if she said nothing and refused me a second date. Many guys have horrible dating skills as Evan said, so he talks about himself trying to impress you. Sure their are braggarts out their, but most of the time the guy is just nervous and wants you to think he is great. Just mention it to him, if he keeps bragging about himself, or gets angry or childish, then you will know.


      The women who always seemed like the best flirts to me, never made me think they were flirting. They were just fun to be around, and I craved more of that feeling from them. In this case, being confident is synonymous with being fun.


      Those are my two cents, good luck! (^_^)

      1. 5.1.1

        Thank you! Yes, I took a week off from dating and cancelled my account on a site I had been using, I was feeling fed up and was going to stay off longer actually but then I met up with a new friend last weekend and she met her boyfriend online and seems very happy so I’m trying that same site (Coffee Meets Bagel) they met on and have my first date tonight from there with a guy I’ve been chatting with. It seems a little more relationship oriented than the one I had been using and that is my ultimate goal so fingers crossed!

        Thank you you for the advice, I’ve gotten a good amount of second, third, fourth dates so maybe I’m doing a better job than I thought but I know from being a reformed super shy girl than I still struggle with it at times and worry I come off as aloof or disinterested. Usually a glass of wine helps too 🙂

        1. Adrian



          PLEASE don’t forget that you are only  HALF of the equation!


          What I mean is, it is good that you are conscious of coming off as disinterested, but some guys just have serious self-esteem issues. So what may seem disinterested, aloof and shy  to one guy, may seem perfectly normal to another.


          I guess I just want you  to have that  happy balance, self-worth, but also humility… I’m working on the balance myself.

        2. Kh77

          Just a quick update, the date last night was awesome. We had a lot of fun and had dinner followed by drinks. Letting him know I was interested came very naturally to me so maybe it depends on the guy as well. Fingers crossed he asks me out again but it makes me glad I gave online dating another chance when I was feeling so fed up with the process. I have another first date this week with another man from the same site, trying not to put my eggs all in one online dating basket even though I’m excited about this other guy.

        3. Christine

          That’s great that your date went well!   I do know how that is, when you’ve met so many Mr. Wrongs that you wonder if Mr. Right is still out there.   A good date will, at the very least, renew your hope that there are good prospects.   I really think a relationship is right around the corner for you and you’re in the right mental place for one.

          But you’re right to not put all your eggs in one basket, after just one date.   You never know.   I’ll cross my fingers that this other guy turns out to be a great prospect too.

        4. Kh77

          Unfortunately I think the great date from Friday is “ghosting” me, he texted over the weekend but didn’t ask for a second date and now he hasn’t replied for over a day so I’m assuming he’s headed off to the island of long lost men and has his boarding pass in hand. I’m still optimistic, chatting with some new guys. I may take a little break again in a couple of weeks if nothing pans out, I know it’s a necessary process but it can be a bit exhausting and I really like to feel mentally refreshed and give anyone new the opportunity to see me in a positive state with an open mind.

        5. Adrian


          Congratulations on a good first date. Just be careful, as Christine just said, if you have too many bad dates, you easily get attached to the person from the good date, even if they aren’t a good candidate.

        6. Kh77

          I’m actually pretty good at sorting through the men and I’d say a good 90% of the time I have a good date, we chat for a couple days prior to meeting and I can tell pretty accurately whether that will translate into real life. My issue is that I get to a couple dates with the guys (or sometimes just one) and then they fade out. I think for some of these guys it’s just a paradox of choice and they want what’s around the corner and to see what’s behind Door #2, I can’t change that. They seem to enjoy the dates and will follow up even saying that after the fact so it can be confusing. This last guy told me he had a lot of fun and then followed up over the weekend only to suddenly ignore me. It’s a bit baffling but I’m trying my best!

      2. 5.1.2

        If I dont want a second date, I ALWAYS insist on paying half but to date, no man has ever allowed me to follow through with that…no kidding.

        Adrian, you make such great points.   Dating should be fun. You shouldn’t feel like you’re on an interview. You shouldn’t feel judged. There should be lots of laughter. You shouldn’t feel like the conversation is awkward. I love that ‘where did the time go’ feeling. But I will say, the problem isn’t that a guy talks too much about himself necessarily, but it’s more about how he balances this by asking about his date as well.

        Let me ask you:

        If a woman did not want a second date with you, how would you prefer to know?



        1. Adrian



          Good question. I would like to know up front, I want to be the type of person that a woman doesn’t feel that she has to do the fade away,  or the not reply to my calls. O


          A better question would have been how would I handle it.

          18 year old me: misdirected Anger and  hurt, felt not attractive

          25 year old me:  same as 18, but ask why,  to better myself

          30 year old me: I don’t take it personal, but  it still stings a little


          I think the  biggest hurtle I had to overcome was having faith in myself. Seeing married friends or friends in happy relationships, while you are single, you start to think that you will never find someone. Subconsciously your actions start to reflect that.


          The most obvious why this is shown is with a lack of patience. You don’t make long term plans as if one day you will no longer be single.

      3. 5.1.3
        Emily, the original


        “And like many women on here have stated, if you don’t want a second date, insist on paying for your half.”

        What is a woman supposed to do? Grab the bill and say, “There will not be a second date. Let me pay my half.”

        I ask because I am going on a date tomorrow with someone I am not super excited about. (I suggested lunch to keep it short and keep the expense down.) He seems pleasant but I don’t have any huge expectations. I just usually say no when I get asked out and I am trying to be more open.




        1. Adrian



          So here I go again, I’m about to sound like a hypocrite, or at the very least contradict my earlier statement, but




          You just don’t want them to feel like an interview. You want them to be fun, and enjoyable, but you are still using that time together to determine if this person is someone you can see yourself with long-term.


          The reason I bring this up is because, it seems like you don’t even want to really be with this guy, so why waste your or his time?


          The method of a woman paying her half of the bill for everything is for women who went on a date with a guy to give him a chance; I think the date itself is a waste for a woman who already knows she is not into the guy.


          When I was in high school, a older woman gave me some great advice that I didn’t see the wisdom in until now because I was too immature.


          She said, “Don’t sacrifice your own wants and desires just to make another happy, happiness should be evenly   given, received, and shared by both.”


          Sacrificing your own heart only looks romantic in movie; Emily don’t just accept a date from someone because you feel sorry for them,


          If I remember correctly from earlier post, it seems like you accepted this date because the guy keep asking, and you finally said yes. So I think at the very least, you should have made it a fun date, so the time would not have been a complete waste (but that’s just my opinion. This may be why women always think the date was great, while I didn’t, and they are surprised I didn’t ask for a second date, so that’s probably not good advice (^_^).

          …    …    …

          Anyway, to answer your question: YES! Insisted on separate bills when the waiter takes your order or when you order at the counter.   Then at the end of the date if you still don’t want a second date, thank him, and than tell him face to face that you don’t want to date him.


          Make sure you tell him directly, because from the way it sounds, he is the kind of guy that if you try to be nice or gentle to spare his feelings, he will take it as you are unsure, which will make him try harder to convince you.


          Many women make things worse by not trying to hurt the guys feelings. Remember what I said up top about sacrificing your own happiness for another’s, be DIRECT.

        2. Tom10

          @ Adrian
          “Anyway, to answer your question: YES! Insisted on separate bills when the waiter takes your order or when you order at the counter.   Then at the end of the date if you still don’t want a second date, thank him, and than tell him face to face that you don’t want to date him.”
          I dunno man, I think you’re stretching a bit here; it just seems so unrealistic. This sounds a lot like women complaining about guys who don’t call them after sex, whereupon all the male contributors pile in to say; “well, I never promised her I would, did I?”
          Therefore, if a guy asks a girl out to dinner and decides to pay the bill, then it’s on him. Whether she decides to go on another date or not is immaterial; she never promised him anything, therefore she doesn’t owe him anything. He just has to write it down as a cost of dating and keep it moving.
          If it becomes a pattern then he should switch to cheaper dates or be more selective in who he chooses to ask out on a date. Just like women who sleep with guys without commitment should be more selective before sex if they want to ensure he calls afterwards.
          “Make sure you tell him directly, because from the way it sounds, he is the kind of guy that if you try to be nice or gentle to spare his feelings, he will take it as you are unsure, which will make him try harder to convince you”
          Again, I’m not sure about that man. Dating isn’t for the feint-hearted, therefore, if a grown man can’t deal with being hurt by being faded-out/ignored/dumped then he shouldn’t really be dating. Expecting someone to be direct just isn’t realistic in today’s dating environment.
          If the guy is unsure where he stands then I think the onus is on him to gauge Emily’s interest (either directly by asking or indirectly by having some modicum of dating skill) rather than being on her to be direct. YMMV.

        3. Tom10

          @ Adrian
          Actually I just re-read my comment there and realized that I misinterpreted your second point. You were telling Emily to be direct so that her guy gets the message (her lack of interest) rather than get his feelings hurt. Either way I think it’s on him to be able to read her level of interest rather than on her to have to spell it out for him.
          For that reason I’d hate to be a woman dating; it must so difficult to shake off guys who just don’t get the message and go-away. Some guys seem to have really poor dating skills.

        4. Emily, the original

          Tom and Adrian,

          I went on the date and this is what happened: He grabbed the bill when the waiter set it on the table. I picked up my purse and said, “Let me help with the bill.” He said no. I then said, “Let me pay the tip.” He again said no. This is something I would have done whether I wanted a second date or not. And my offer wasn’t a test. I do not assume the man is going to pay.

          And, no, I probably wouldn’t tell a man to his face that I didn’t want to go out again. That is very difficult to do, especially when it’s someone you don’t know well because you are on the first date. I would, however, respond to a phone call or text from him asking for another date that I didn’t feel we were a match. I think ghosting is rude.

        5. Adrian



          So what is the outcome? It seems like you still don’t like him, did he get the hint, or is he still trying? If the latter, did you let him know how you feel?

        6. Adrian


          I was going to say that you are a veteran on this site and you should know better, but I was looking at some of your old comments and it seems that you  have been  saying the same thing for a long time  (I’m not saying that in a negative way).


          If it was really just as simple as, men knowing the consequences  of asking her out (the rules of dating), you would not have literally hundreds of comments on this site alone by bitter angry men. Or the creation of the whatever that group Evan is always talking about who bash woman and say every man should get a foreign woman is.


          Please don’t think that I am disagreeing with you, I am not. I just think that this is a case of “what is vs what should be”.

        7. Tom10

          “I just think that this is a case of “what is vs what should be”.
          Well that’s the point isn’t it? There *is* no “what should be”; there *is* only “what is”. Therefore arguing how one “should” behave is moot as it will always come down to subjective opinion of what constitutes rude or ethical dating etiquette. Some will say it’s rude for a woman to accept a date from a guy she’s not really into, on the chance he might grow on her; others will say it’s not. Some will say it’s rude for her not to tell a guy face to face that she doesn’t want to see him again for a second date, as you said your previous comment; others will say it’s not.
          So, ultimately, discussing subjective opinions on what is/isn’t rude misses the actual point of this blog; which is to discuss and implement *effective* dating strategies.
          And, in my opinion, the most successful strategy involves each individual taking personal control and responsibility for their goals and actions. Or acting as the CEO of your love life as Evan calls it. And this is the perspective from which all of my comments originate.
          So if one dates from this perspective then they will refuse to blame the behavior of other’s and as a result will become less bitter, less negative and less burned out. So when women fade me out after a few dates I refuse to get upset with them. When women ignore my calls/texts after a few dates I refuse to get upset with them. It’s on me how much time/energy/money I choose to invest in a woman without commitment, therefore, it’s on me to not be upset if she then decides to move on if it suits her.
          So yeah, when I read the “hundreds of comments on this site alone by bitter angry men” I still feel the same: it’s on them to learn how to change their attitude and become better daters. Not on the women they date to change their behavior.

        8. Emily, the original


          The date was perfectly pleasant and appropriate. He texted two days later and asked if I wanted to go out again. I texted back and thanked him for the date but said I’d rather we remain friends. He replied ok but an hour later texted again to say he felt the same way and was asking because he couldn’t read me. That kind of irritated me. Why ask me out only to tell me you wanted to be friends after I say no? So either that was a self-preservation text or he really was feeling like the connection was a friendship. Who knows? This is why I don’t like dating. It feels like a game of one-upmanship.

    2. 5.2

      Well, unfortunately the guy from the date on Friday has ghosted me, he texted Saturday and Sunday after our date making small talk but not asking for a second date and then my last text (asking how an audition went) went ignored since Sunday evening. I’ve deleted his number to prevent any additional texting temptations and have a date I’m looking forward to this next Friday. Hopefully the next guy won’t be flaky! It was a fun date and gives me hope but very frustrating when they bother to follow up after the date and then vanish. He even told me how much fun he had the night of the date in a text after he got home. Oh well. On to the next!

      1. 5.2.1


        This was the reason I asked that third question. I think sometimes people are so into the moment, but it has no real foundation. So when they think about it, they realize that the date wasn’t that great, or like you said, they find someone better.


        Either way, I know it hurts, but I would rather be told upfront that they don’t want to see me again, than for them to play with my emotions by flirting, texting, and talking to me one or twice more before fading away.


        Good luck on your next date.

        1. Kh77

          Thanks, I wouldn’t really expect him to give me an explanation after only one date but I could have done without the follow up texts (initiated by him) the following two days and texting me after to say he had a really fun time. I suppose that is a skill in and of itself, if you aren’t 100% sure you want to see someone again give it a day or two before reaching out and realize additional contact is perceived as interest. If he was 100% sure then he just seems flaky to suddenly change his mind. It happens in online dating especially. It was genuinely a fun date and I had a great evening, it just wasn’t in the stars 🙂

        2. Christine

          Oh well, on to the next!   It sounds like you’ve got the right attitude and perspective on it.   That’s just how online dating goes.   It happened to me more times than I could count.   Eventually you’ll get the non-flake who knows he wants you and will keep wanting to see you!


  6. 6
    Emily, the original


    No, I am not going to tell the waiter to bring separate checks when the waiter takes our order. That seems rude. That is announcing, after spending exactly 5 minutes with my date, that I have already decided I don’t want to see him again.

    This is a new person. I have not made reference to him before on this site. From what I have read on other dating websites and from what I have heard from friends, many women will say yes to a first date with a man they feel “meh” about. To be honest, I would have to go back years to remember going on a first date with a man I felt excited about. But that is on me. If a woman can’t find anyone to date, she is doing what I call over-filtering and shooting down everyone. That can’t be healthy or productive.

  7. 7

    Oops typo!
    “Be yourself” was great dating advice back when having social skills was the norm.

    My grandparents met and married  at time when dating more or less followed a script, tight knit communities made sure people looked out for one another, and lacking  social graces reflected poorly not only on you but also on your family, so you acted right in public and wouldn’t dare let word get out that you had “no home training.”

    Today it seems that having a filter in one’s social interactions and being able to read  social cues is as passe a skill set as writing  in cursive.  A lot of people out there dating just have not learned social skills or haven’t had to hone  them because their longest relationship  has been  with their smartphone. And the younger they are, the worse it  is.

    The stories I hear from my 20 something nieces and nephews: the girls complain about late night texts from guys they  haven’t even met in person  yet that result in verbal assaults when they’re not answered, that the boys can’t even begin to figure out how to properly ask a girl out and expect them to accept coming over to his apartment to be ignored all night while he plays video games as a date, the boys complain about girls who cuss them out when they try to make conversation,  girls who go out on dates with them and  spend all night on their phone.

    I see alot of my peers in their 30s and 40s replicating this behavior in the sense that they see investing in traditional courtship as a waste of time and just want to get to their end goal as fast and with as little effort as possible, which results in poor form (dick pics, random propositions from strangers on  dating sites, inability to maintain date conversation, men  who won’t take no for answer). Online dating only compounds it  because people are using  it as the end rather than the means to the end.

    I think that  to stop feeling unending frustration and successfully date today we  have to go back to the basics of social interaction and expectation.  Intimacy is the precursor to thriving relationship and it  can’t develop  with out meaningful interaction. Romance is  one thing that can’t be made easier  by technology.

  8. 8

    I see your point, although I think the point of the advice is to not pretend to be something you’re not, not to completely avoid any introspection, self criticism of self improvement.   Taken to the extreme, yes, it is a bad idea to keep making the same mistakes in the vein of just being yourself.   But I also think that a relationship is unlikely to work if one person enters into it pretending to be someone else or pretending to conform in ways that are not sustainable in the long term.

    I know that there are some things I’m not willing to compromise on and I know full well that it might mean I’m single forever.   But life has taught me that those things are important.   Certainly other things I have changed and I know that in many ways, I’m a better partner today than I was when I was 22.   Age hopefully brings self awareness.

  9. 9


    “clinical basis”? You have got to be kidding, right? This isn’t exactly physics or chemistry we are talking about. There’s no “clinical basis” for anything in dating and certainly the “expert” you are quoting did not conduct clinical research to substantiate his theories. This is all just talk and opinions. And, to that end I am allowed to define casual sex as I see fit.


  10. 10

    Realize I posted twice because my other comment from hours ago still wasn’t approved and I thought it was deleted because I didn’t see it. I’ve just been ghosted once 😉

  11. 11

    Nice podcast. Though surprised that Evan was not a good dater in the beginning! Say it ain’t so! Evan, I do wonder how you went from not knowing ‘the rules’, to figuring things out and then becoming a dating coach. A lot of men fight against this process (and women too.) Where you just so unsuccessful that you started to look inward? I do like the advice of asking select past dates what you can do to improve.

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