Dating the Divorced Guy – an interview with Jonathon Aslay

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There aren’t many men who do what I do, but Jonathon Aslay is one of them. He’s a good friend who helps middle-aged divorced women through the dating process. Although, he is one of the sweetest guys in the world, we tussle in the middle of this podcast about what kind of questions you should ask on the first date. It’s juicy stuff and useful to see things from both sides. Lemme know what you think.

To learn more about Jonathon Aslay, click here to visit his site.

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  1. 1

    This has been Evan’s BEST interview to me!  

    This is the first time I ever wanted to listen to one of Evan’s podcast more than once.

    I have to agree with Evan, even when  Jonathon reframed the questions politely, they still screamed test to me-being tested is insulting.

    But on the other hand, I can see where Jonathon is coming from by saying someone should not have to fake or lie about who they are just to win a man or woman-it is “perceived” as degrading.

    Plus as Jonathon said to spend weeks becoming emotionally invested in someone just to find out that they have a Huge deal breaker is heartbreaking.

    Also as Jonathon brought up, shouldn’t a man deciding to treat a woman financially on a date be seen as something voluntary? A positive part of his personality, so how is a woman requiring a man pay the first few dates not a test? Seems like a double standard.

    ….       …..       …..

    Jonathon really opened my eyes today. I never realized how unbeneficial it is to date a divorced person; I never though about it before but it seems “for me” they are best to be avoided in dating, especially as Jonathon said, someone who married young and divorced 20 years later.

    ….      …..      ….

    As far as waiting to tell people things that could cause them to break up with you, I wonder what is the difference between just being a manipulative person and a person who waits until you are invested in them emotionally before telling you something huge because they know you will stay?

    ….      …..      …..

    If a person told me while we were in the bed room right before sex that she had an STD, I would be completely blinded!

    Being in love with that person would make it worse because then I would be conflicted and feeling guilty. I would not want them to feel ashamed, but at the same time I would be hurt and angry that they waited to tell me.

    Though Evan is right, if they would have told me before I become emotionally invested, I would not have even hesitated for a second to end the relationship.

    1. 1.1

      Adrian, he’s saying to be mindful of someone who is very recently divorced or still separated, not to avoid divorced people entirely! He also seems to be talking about divorced men specifically with kids, definitely not all divorced people.

      Depending on your age group, if you avoid all divorced people, you’re really narrowing your dating pool. There is also something to be said about people in a certain age group who’ve never been married. You could judge them too, if you’re that way inclined, as potentially commitment phobic etc.. Never, ever date based on fear and negativity. You’ll have a lot more luck and enjoy it more if you’re more open minded & don’t assume things about a certain group of people based on one interview.

    2. 1.2

      Hi Adrian,

      I don’t think that divorced people are to be avoided as dates and potential partners.   Marika is right, once you get past the late 30s age range, a lot of the single people you meet will be divorced or will have been in long term living-together relationships.   In general, people who have been divorced want to be in a relationship, they just had one fail.   Once they have that 18 months to 2 years after the divorce to grieve and to get their feet back on the ground, they themselves aren’t any more of a relationship risk than someone who has never been married.

      There are considerations if someone has children and has to work around joint custody issues.   If you are in an LTR with someone who is a parent, you have to be ready to take on a step-parenting role.   It’s entirely reasonable to not want to take that on in a partner, especially if you are young (20’s to mid 30s) and there are still plenty of never-been-marrieds in your dating pool.

      As far as Jonathan’s advice to put it all out there up front, vs. Evan’s advice to reveal yourself organically over time, I think it’s a balancing act.   If you really are compatable with someone, you will be able to discuss awkward or difficult topics in due time. If someone dumps all of their negatives on you upfront, it can be a turnoff since you’re missing nuance and context.   On the other hand a person keeping something major from you for a long period of time, because they “know” you will dump them if they  reveal it, can indicate the  person has serious trust issues and/or anxiety issues.

      Another thing to consider is how such information and questions are delivered.   If  a man said to me on a first date, “My ex-girlfriend is my best friend.   I hope you don’t have a problem with that.”   I would really feel put on the spot.   However, if we had an ongoing rapport where maybe he told me a funny story about something that happened to his best friend “Jane” and later I found out how they originally met, then I haven’t been put on the spot and I’ve also gotten to know something about how they became friends and how that friendship operates.


      1. 1.2.1
        Kareen Loy

        Very good points go with the flow.

    3. 1.3

      Jonathon really opened my eyes today. I never realized how unbeneficial it is to date a divorced person; I never though about it before but it seems “for me” they are best to be avoided in dating, especially as Jonathon said, someone who married young and divorced 20 years later.

      I had read your comment before I listened to the podcast. I thought it would be very negative about divorced men.   It was and wasn’t.   I think Johnathan recommends a healthy caution and just advises to give divorced folks enough time to heal.

      1. 1.3.1

        Hi S,

        In comment #25 you said “I didn’t get all of my questions answered in the podcast but I remain cautious with divorced guys. Most I meet, even ten years later after the divorce, are still stuck on that relationship.   Not the  woman, but that marriage casts a wide shadow.

        ^^^This was the impression I was getting from Jonathan’s advice. It was not necessarily the ex that they are stuck on but the repercussions of the divorce, such as: lacking dating experience from marrying young, not realizing that they want to play the field and see what is out their, being stubborn or stuck in their ways because while married they did it like that for years, bemoaning their lost time, lost money, their lost youth, paying for children, going in debt as a result of the divorce, paying alimony, losing the house or car, not having the time to spontaneously date if they have children, refusal to do certain things or give certain things in the relationship because of how their ex responded to it, etc

        Their are a lot of great divorced women and men out their, I just never considered the work I would have to go through dating them just to find a good one.

        1. S.

          Ah, I see now.   Before I listened to the podcast myself, on your comment alone it sounded like dating a divorced person would be a negative thing.

          But good to know it’s work.   One of my friends (divorced twice) says it’s always work. Young people, older people. Never married, divorced.   People come with baggage.   I guess it’s up to us to choose which baggage we want to work with and if the person is worth it.

  2. 2

    Video won’t load.

    1. 2.1

      Thanks for letting us know, KK.

      1. 2.1.1

        Working now. Thank you!

  3. 3

    i totally agree with Evan here. I most likely eventually wouldn’t have a problem with a guy i’m in love with keeping a friendship with his ex. However, if he put it out there on the first date it would REALLY turn me off.

  4. 4

    This podcast is indeed one of the better ones. I like the back and forth of your discussions, and I really liked the fact that you both argued your views very well, while still being respectful towards each other.

    I like that  Jonathan doesn’t demonize divorce. He’s done it, he had the ambition to marry and he made a good effort at it. They are not automatically problematic people, that will guarantee a bad relationship for the next person in line. I am glad you are so positive about people who have been through something that can still be stigmatized by society.

    If asking direct questions works for you, go for it. People are usually pretty honest, they feel no need to lie about where they are in their lives, and what their goals and priorities are. And yes, qualifying your prospect is very important. I find that people reveal themselves very quickly. Evan advocates that you need a couple of months toget to know someone initially, but people usually show their true colours WAY before the two months are up. They really do vomit up the information, as Evan says, whether it’s through organic conversation or as a result of being asked direct questions.

    Having said that, if someone  said the following on a first date, i would be extremely reluctant to go on the second date.

    ‘Tell me more about your  traumatic childhood after my probing question caught you out.’ I would avoid such types of questions or answer in a very bland manner as i think that is way too TMI. As for that being an eventual dealbreaker, i would hope that the person i am dating would develop a broader view on people who didn’t have the sunniest childhood ever. Speaking from personal experience, my  (sometimes) traumatic childhood was difficult to come to terms with when i was an adult but it taught me  grit, resilience and, most important of all, a greater  empathy towards others. Adults evolve, and not all are the puppets of the childhood that was thrust upon them. They bring added wisdom, just like the divorced people  Jonathan mentions later in the podcast.

    ‘I am best friends with my ex.’ I would wonder why on earth you would be telling me this on the first date. Are you secretly pining for her,  hoping you will stay in touch at a later date? Are you going to talk about her endlessly? Please note that it is not the fact that your ex is your best friend (That’s cool, it shows you are able to form healthy relationships with the past women in your life), but that you felt the burning need to tell me during our first date.

    Lastly, I LOVE that you want to take turns in paying the check. It makes the women feel less like they are being paid for favours due, but more as equal partners for whom you have much more to offer than a well stocked bank account.


  5. 5

    The topic is a great eye opener.

  6. 6
    T ken

    What a great interview, thank you.

    I’ve been divorced for over 10 years, involved with two LTR. In both cases, the men had old girlfriends they either supported financially and continued to stay in touch with and both, when I asked to have her over for dinner with the   two of us, declined. There is so much more to these stories but suffice to say, it took years for me to rebuild trust in myself and my choices.   Now, here’s the deal, I tried being “cool” and “grown up” about these two relationships as we were building our own but in the end, it shattered trust and came damn close to shattering me.

    Jonathon’s ex-girlfriend being his best friend is very cool. But, I would dare say, if he told me that on the first or second date 1) I’m sure I would have a inner reaction 2) If I asked honest questions of it, I would feel defensiveness and push back, more importantly, I’d like to be reassured I wasn’t an accessory to it.

    Does that make me not “grown up”?

    My grown-up response would be “when can I meet her?” and right along side of it would be some insecurity and curiosity, would he judge that in me?

    We are the sum of our own experiences. I’d like to think I stay open to all the possibilities, I search my own beliefs ,   the reasons for attracting men who are not 100% available.   I take 100% responsibility for my choices and…this one confuses me.


  7. 7

    My dating thus far has been more in line with Jonathan. Unfortunately, hasn’t gone too well. Taking more of Evan’s advice and I’m getting better results. As Evan said, anyone can give you lip service and answer the questions “correctly”. The proof is in the behavior and it takes time. Have fun, observe, and see how things unfold.

  8. 8

    I don’t always agree with Evan but I would rather be on a first date with him than Jonathon 🙂 Being “tested” is a huge turn off and I am 100% in agreement with Evan that the first date is for having fun and getting to know each other organically.

    However Evan may not like my preference to take turns planning and treating. The country   I live in is more egalitarian than the US and it would be make me uncomfortable to have a guy pay every time.

    1. 8.1

      I’m glad you raised this, Michelle. I agree that there are cultural differences that we need to consider when implementing this advice. While the underlying message is always fantastic, personally I think sticking rigidly to all Evan’s advice like ‘rules’ if you’re from a different culture is not  always a good idea.

      If we waited for  men to initiate all the contact, plan all the dates and pay, even in the early stages of dating, the marriage rate in Australia would plummet! Men just aren’t quite as forward and confident in all cultures. After the first or second date here, you would definitely need to start doing some planning and paying, or the guy would either think you weren’t interested or feel used.

      The only men I’ve known to keep pursuing me even when I wasn’t planning anything in return (and in my 2 1/2 years of being single I could give Evan a run for his money in how many dates I’ve had!) were guys who were either clueless or insensitive/narcissistic guys who didn’t care about my feelings and pursued relentlessly anyway. For most guys here, no matter how happy you were to hear from them & how much you enjoyed the dates, if you didn’t make an effort to make plans, they’d think they were respecting your feelings by backing off (or, sometimes they’re just lazy!).

      Certainly, though, I’ve taken on board the importance of being the cool, fun girl (I personally think that is excellent advice and much better than being intense & testing people), being grateful, happy , kind, mirroring his efforts & not overfunctioning. I always take on board as much as I can and modify as needed.

      1. 8.1.1

        Hi Marika,

        I would be curious to know based upon what you have learned either from this site or other places about how we date here in the United States;

        What similarities and differences are there in how Americans go about dating and how Australians go about dating?

        How does the whole dating process, courting, male and female rolls work in your country of Australia?

        1. Marika

          Thanks for your question, Adrian. It’s a really broad question though! I think the main thing is that it appears to me that fewer men in Australia compared to America are confident ‘alpha’ males when it comes to relating to women, not at work or in sporting settings or with their friends – different story. Overall they are less likely to be really proactive in dating. Some may pay for the first and maybe second dates, but in my experience, after that it’s typically 50/50. I’ve also been asked around at least 1/3 of the time to chip in for the first date. They often ask the woman where she would like to go, rather than plan it and then invite her, and if with coaxing they do make a plan, they   won’t typically be very creative in their choices. A first date will also often be quite low key (like ‘drinks’ without dinner or coffee), so even if they are paying, it won’t be a lot.

          I don’t think this is because they don’t care or are rude or bad, and none of this is ‘wrong’ perse, I think it is more that they treat dating as a 50/50 type thing, or are more laid back people in general, or are less sure of themselves and worried about making a mistake (what Evan would call a beta male). My very alpha ex husband was quite wishy washy & unsure when it came to taking me out  (e.g let’s go to the local club for a steak was the most exciting it got until I starting planning our outings!).

          We don’t have as much of a dating culture either. People tend to get together  early, in school,work or university, as friends or through mutual friends and just sort of ‘fall’ into relationships, rather than actively date (I didn’t officially ‘date’ until I got divorced  in my 30s).

          Obviously I don’t live in the US (have been there, though), but whenever I’ve met American guys, or they contact me online, and in general, American men have a reputation as being much more confident and proactive. It’s rare to get approached by a man you’ve never met in a pub here (and unheard of say in a cafe or on the street/bus), but when I was in the States it happened – and other people have told me this too. American men seem to handle you saying no to them with confidence and ease too (in my experience), or more so than here. When I got approached when I was in America, I was in a relationship, so had to say no, and it didn’t bother them at all! I think men here may be a bit less thick skinned. They’d also try to find out if you were with anyone before approaching you – which is why bars are safer than elsewhere, as you’d often either be single and looking, or clearly with your partner at the bar.

          The men who write to me online who are American always write very confident, funny, flirty emails – I tell them that they should give lessons to the Aussies, haha – who are much more likely to write “hi”, “hey beautiful”, “I like your pics” etc.. 😉

          Hope that answers your question!

        2. Kanga

          Wow, I’m also Australian and whilst I agree on the ‘don’t really date’ thing in Australia and also guys aren’t super up front and will drop off pretty quickly after the second date, if you aren’t pro active (phew – that makes it easy), but almost every time I’ve been in a pub I’ve been approached by a stranger and also outside of pubs. If I went into a pub right now (I live practically across the road from one, lol and can hear it right now)   – I’m certain I could walk out with a number. In fact, the last guy I went on more than one date with was a stranger in a pub, at a pool tournament. We became quite good friends. I don’t even play pool!   Men are less likely to approach if you are in a big group, but one, two or three ladies will definitely get approached in my experience. I rarely go to pubs anymore – it’s not my scene as the only reason men are approaching you in a pub here is for sex and I’m getting too old for the noise and alcohol.

      2. 8.1.2

        Haha yes I’m an immigrant in NZ so quite a bit of what you say here and in your comments below apply to us here as well! 😀 I found “dating” (as you say, not much of a dating culture) a bit of a struggle and am very happy now with a fellow international from my own country.

        1. GoWiththeFlow

          Michelle, Kanga, and Malika,

          As someone who would like to work internationally in my field once the kids are out of the house, I find this thread just fascinating!   Thank you!

        2. Tom10

          @ GoWiththFlow, Michelle, Kanga and Malika
          Just to add that the experiences you describe in Australia are pretty similar to dating here in Ireland. Asking women out in random places such as shops, streets, bus stations etc. is just unheard of. Indeed, when locals observe American guys over here do it we marvel at their audacity.
          Guys here will also cut women off very quickly if she makes no effort to contribute from early in the dating process; even after one or two dates. I’ve found though that women here  can even  prefer to pay their own way as it means that they then  don’t “owe” us anything and so can cut us off fairly easily if/when they want to move on!

        3. Henriette

          Same as my experiences here in Canada.   People are more reserved here, so even trying to strike up a (purely platonic) conversation with a stranger when we’re both waiting in a long line just to help pass the time, is often met with awkwardness or suspicion.   And rather than a “dating” culture, people tend to just meet up in groups and then pair off with someone from that group, say, or hook up with someone they know from university or work.

        4. Kanga


          I agree about the paying thing – I’m more likely to want to pay if I don’t like the guy, just so I don’t owe him anything and there are no bad feelings. I also buy drinks for the guy or whatever, wherever we are.   My last relationship was with a rich, middle eastern man and it was an affront to him if I offered anything and also our earnings were severely mismatched but it still made me awkward having him pay for everything and the times I did pay for things he would sneak money into my car or wallet for me to find later.

          Maybe a sign in Australia is – if she’s paying half on the first date – you are never going to see her again!! Because in my mind that’s actually true. Also, the not taking charge of where to go etc. does happen here – the last guy I went to dinner with didn’t ask me until we were in his car where we wanted to go. That kind of thing drives me mad at my age. I’m new to this town and I just wanted to go to dinner not have a half hour conversation of where we should go etc. It took us an hour to get to dinner and I let him pay, lol, because I was so annoyed. He also turned up in a t-shirt and joggers… Australia is a super casual country – but, come on!!

          People tend to ‘fall’ into relationships here I think and if it doesn’t happen when you’re young and socialising a lot, you might find yourself on the shelf with some very long dry spells, unless you are into the pub culture, which won’t find you any kind of quality partners at all.

  9. 9

    I think Evan and Jonathon both made valid points, but I do wish men followed Jonathon’s approach. It sure would make life easier.

    1. 9.1

      Hi KK,

      As to your comment about the video: I don’t like the videos as much as I like the podcast. I get to easily distracted by facial gestures and body movement to actually focus 100% on the listening. I have noticed that I can easily miss little things that were spoken.

      …    …    …

      Anyway, what parts of Jonathon’s approach do you wish we followed more and how do you see it as making life easier?

      1. 9.1.1

        Hi Adrian,

        The tell-all, upfront, honest approach makes it easier to eliminate people earlier that aren’t compatible.

  10. 10

    I’d have to agree with Evan that “I’m best friends with my ex” very much comes across as a test. To me, when someone is worried about ‘not wasting time’ it is generally a cover for fear that the person is not realizing they have. Sorry. I do think Evan could have let Jonathan talk more though, and let the listeners form their own opinions about the validity of that advice, without making Jonathan feel like he was being made wrong.

    I’d be interested in WHY this guy is best friends with his ex. Was she the one that got away, and he never got over it? Is she filling the emotional hole until a new girlfriend shows up, and he plans to let go of the ex/emotional blankie when he has a new blankie? Is he friendzoned, hoping she’ll eventually make him a friend with benefits? Most men don’t have women friends unless they are hoping for more (yes, Evan’s an exception because he just loves the attention and the talk). Even women with men friends usually are hoping the man will eventually notice them as more.

    It’s been my experience that men in general are gun shy and prone to seizing on the smallest thing if you tell them too soon. Have Him At Hello confirms this also. Because they don’t know you well enough to put it in context, they make inaccurate assumptions. Heck, I’m even afraid to mention that I like watching movies with the subtitles on, because who needs an argument on the first few dates?

    What other things don’t you guys mention on a first date?


  11. 11

    Evan, I love your advice and am a big fan of yours.   So it was disappointing to hear you dominate the conversation, interrupt your guest to the point that he needed to shout over you   and to make him wrong. It was a trial to listen to. The wrong time to spar.

    1. 11.1
      Evan Marc Katz

      Dear Alex,

      I am sorry that you did not find my free podcast to be worth the money you didn’t pay for it. I’ll admit: I’m not a professional interviewer. I’m a reality-based dating coach who offers advice based on what’s most “effective”. Not based on what I like the most. Not based on your feelings. Not based on what looks good. Based on what works.

      The reason I put up such a fight with Jonathon – and he knows this – is the same reason I wrote this post about Rori Raye’s Circular Dating

      This isn’t a simple point of agreeing to disagree; I actually think Aslay’s advice is ineffective and counterproductive to anyone who is trying to make a great first impression on a date. It’s based in fear, insecurity, and scarcity. It says, “I’m an adult. I know what’s others think is wrong with me. I’m going to tell you up front so you can’t be surprised. Now, tell me what you like to do for fun.”

      Except that’s not how it works.

      If you doubt me, go ahead and interview your next date to ensure that you’re marriage-compatible from the get-go. And while you’re at it, be really up front and truthful about your perceived issues. Jonathon’s were that he’s best friends with his ex, that he’s a beta male who doesn’t like to play the traditional masculine role, and that he doesn’t want to court you by paying for everything. Fair enough stances. Attractive to tell someone on the first date? Uh uh.

      Here’s one of my women clients telling the truth to her first date – in the name of honesty and not wasting time. “I am afraid of not being good enough and being abandoned. I’ve got a history of being a doormat in relationships. I take Zoloft for my anxiety. I have issues around men, sex, and trust.”

      Hey, it’s the truth – and if he can’t handle it, that’s HIS problem, right?

      So this isn’t a matter of politics or religion, where two people can stand on different sides of an issue. There’s only what works. I have yet to see any evidence that some guy saying, “I’m BFF’s with my ex. Take or leave it,” or “I’m 39 and want to be pregnant in 18 months,” is an EFFECTIVE way to communicate on a date.

      1. 11.1.1

        For the last two years your advice has been right on the money and has saved me from a lot of heartbreak- at 31 I’ve been able to effectively weed out uncompatible men and now am with a kind and considerate alpha, what you refer to as the ‘nice guy with balls’. Can’t help but agree with you again in this podcast.

      2. 11.1.2

        Evan was correct on this one for sure. The things Jonathan tells early would make anyone walk away immediately. If I was a woman I wouldn’t take this guys advice on many issues that was discussed. Although Evan, waiting til we get to the bedroom is not the right time to discuss STI status either. Being a a guy in my 50’s this was a fun podcast to watch I will say. Great topic Evan!

      3. 11.1.3
        Kareen Loy

        Evan i remember reading an article in which you critiqued Rori Raye’s circular dating. It had some very valid points. I will re read it. I suppose everything at times depend on the persons culture.

      4. 11.1.4

        I agree with Alex.

        It wasn’t the advice you gave that wasn’t worth listening to, it was the constant interruptions and talking over Jonathon that made it hard to listen to. I appreciate the banter, but please let your guest finish his point before you state your opinion.

        FWIW, I agreed with your point of view on most of the things you talked about, but he offered a really interesting viewpoint and I couldn’t help but admire Jonathon’s direct approach.

        Thank you for all that you do!

      5. 11.1.5

        This interview made me so glad that I found Evan’s advice first. I would have related to Jonathan’s advice and continued to do what I was an expert at, rejecting men so I wouldn’t waste my time. Evan’s approach gave me a new set of tools to be open to different types of men. That’s how I as a liberally raised woman ended up with a guy who is a conservative, carnivor,NRA supporting, total opposite of what I thought would be a good fit. Now that we’ve been together for three years, and live happily together, all I can see are his excellent partner skills, how he makes me feels cherished. We’ve just learned not to have conversations about gun control.

        Thank you for what you do.

  12. 12

    I used to be the girl who quizzed guys and “didn’t want to waste my time”. Eventually one guy said to me “I feel like I’m on a job interview”. I stopped doing this and sought advice immediately. Which is how I ended up here. Couldn’t agree more, Evan 🙂 Thank you.

    Never went as far as to put all my negative traits on the table from day 1! That’s just plain scary…

    1. 12.1

      I put a lot of deep personal info out there to my boyfriend on our second “date” (we met while on holiday) but that was because I never expected it to develop into a real relationship and I was just being in the moment with a near-stranger. It didn’t have a negative effect on our relationship but that is definitely the exception not the rule and I wouldn’t recommend it! I have some mental health issues and it took a lot of guts to disclose that but I waited until he got to know me as a solid, healthy and positive person first. He took it in stride and it’s all been fine, but definitely not something I would have opened with!

  13. 13

    I would date Evan and would run a mile from Jonathon.   Any man that would tell me he expects us to take turns in paying, and lets me know his ex is important to him is not making me feel special. Jonathon has more red flags than a communist parade. I bet he’s still single !!!!

    1. 13.1

      I bet you are single!

      1. 13.1.1

        I am not single Albert. Married 20 years, then divorced. I was single for 4 years and during that time followed Evan. I have been in a relationship for the past 5 years.


    2. 13.2

      Amen Laine!!! I wouldn’t feel comfortable.

    3. 13.3

      When a guy tells me he wants me to pay for dates that right off the bat tells me someone is more concerned with things being fair then making me feel cherished. And he’s probably going to keep tabs and make sure it’s fair.

      My boyfriend of three years still pays for most of our dates, and when I treat him he always let me know it’s appreciated. It’s fun for me because I am doing it out of love, not expectation. If a guy pushed the check to me and said, “it’s your turn,” it would take all the joy out of the experience. And I doubt I’d feel attracted to him because there is something so passive in that gesture.


  14. 14
    Elly Klein

    It’s amusing to me that so many people found this podcast enjoyable. I found the bickering grating to my ears. And I totally agreed with Evan. Sorry, Jonathan, but while I know your intentions are pure, I think you might be doing many of your clients out of a loving relationship. There’s a time to speak up. And there’s a time to shut up. I think Evan’s advice nails it.

    1. 14.1

      Hello Elly,

      The reason why I personally enjoyed this podcast so much is because it allowed me to see counter-arguments to many of Evan’s belief’s.

      Let’s be real here, as his conversation with Jonathon exemplified, there are many different successful approaches to courting and dating NOT just one; those of us who follow Evan’s advice are choosing to do so because we believe in him NOT because it is the only way.

      So whenever I can get the chance to see those beliefs put to the test, so to speak, and weigh how they hold up against other popular methods of dating; I love that! It either affirms or condemns my choice of following Evan’s advice.

      I will say though that I disagree with both you and Evan in that Jonathan’s way is wrong, again I think it is about the journey not the destination; because I am sure that many of Jonathan’s clients have successful relationships because of his advice just like many PUA’s and “The Rules” clients have successful relationships from following their advice.

      Again I trust and follow Evan’s advice because “to me” he has proven to be someone that is worth following NOT because his advice is infallible or the “only” way to get a lasting relationship.

      …    …    …

      I also have to say that at least to my knowledge, I am an anomaly here in the EMK community. Because I literally “only” follow Evan’s advice, while most of his other reader are more akin to bargain shoppers.

      They have dozens of relationship advice blogs, websites, and coaches they listen to; picking only the parts they like best from them and if the coach says something they disagree with on a subject, they just go to the coach whose advice confirms their beliefs.

      If Evan says something I disagree with or don’t understand, I’ll still follow it to see if it works, because again I believe in him. So seeing his advice hold up against apposing views benefits me.


      1. 14.1.1
        Elly Klein

        Thanks, Adrian.

        To be clear, I don’t agree with 100% of Evan’s advice. (Sorry, Evan. But I know this isn’t news to you… wink, wink.) But I do 100% agree with  his advice in this instance.

        Evan and I are very similar in the sense that we’re both extremely open, honest and upfront. But I felt as though Jonathon’s approach was: a) WAY too upfront, and b) leaves no room to simply get to know and like someone first. For most people, online dating feels artificial enough without turning it  into a SWOT analysis. (Marketing 101: Strengths, Weaknesses, Opportunities, Threats.)

        The reality is your Mr/Ms Right in real life is often not quite your Mr/Ms Right on paper. It’s so important to give someone a chance to warm up to you, and you to them, before you put  each other  in a position of having to decide whether or not  you’re willing to accept certain things. Evan gave some great examples from his own life: If he told his Catholic wife within the first few dates that he wanted to raise his kids Jewish, she  would have run. And if she’d told her financially responsible husband within the first few dates that she was $40K in debt, he would have run. But look at them now – happy has clams. Because they fell in love, had a great relationship, and both felt these things were worth working through. I could say the same for my own wonderful relationship. And I think if you polled your happily married friends, you’d get a similar response.

        Absolutely do not wait too long to ask those serious questions and have those important discussions. But don’t overcorrect to the point of ruling out almost every romantic prospect out before you’ve even had any fun getting to know each other. Truly clicking with someone is rare, so when it happens, most people are willing  move mountains to be together. That’s true love!


  15. 15
    Puzzled By Avoidantly Attached Dating Coach

    Jonathan, it seems to me that you are an avoidant attached guy who is starting out a relationship by telling your date on sentence 2 that you will be cheating emotionally on her and if she doesn’t like it, to move on. It would narrow your pool to find a woman who is willing to share your emotional attention with an ex who isn’t even the mother of your child. I would ask, “What do you need me for, if you already have another woman as your best friend?”

    As a woman who values connection ,   communication and intimacy in a relationship ,   it sounds like a three is a crowd situation and you restrict the partnership by putting your ex as a priority before we even start .

    I like your directness in what you’re looking for, but it can be done in a way that is beneficial for both partners, not just you and your ex.

    1. 15.1


  16. 16

    I am just going to say it. An ex who is not  the mother of a man’s child should have no place in his life. May be you grab drinks once a year to “catch up”, but even that is too much if there’s another relationship.   However, if this is   a guy’s bottom line, I prefer to hear about it right away. I don’t want to waste my time and emotional bandwidth on someone like that – we’re not a good match.

    When you’re dating a divorced person (and as you get older that’s pretty much what your pool becomes), there’s understandable amount of baggage that comes with it. Some baggage is inevitable and you just need to deal with it (i.e. kids). Other baggage needs to be checked at the gate (i.e. “my ex wife is my best friend”. Reality check: No. She’s not).

    Even with the “right” type of baggage sometimes it won’t really work.  I once met a wonderful men who I would love to date, but he was divorced with two young kids and he had a nice setup where they and his ex lived in a house that he owned, and he lived nearby, and he had it all figured out in terms of HIS schedule and HIS commute and HIS preferences in terms of lifestyle, etc. It became pretty clear that he was trying to sell me on his vision of how things should work and it wasn’t my vision. I felt like he was looking for a missing piece of a jigsaw puzzle to fit in his otherwise figured out life, and I was just the wrong shape.  I cut it off very quickly. Even if you’re divorced, I think it’s important to understand that going forward you’re trying to build a new life together with another person, not merely fit that other person in your setup (though if you try long and hard chances are the latter can be accomplished..)

    1. 16.1

      An ex who is not  the mother of a man’s child should have no place in his life. May be you grab drinks once a year to “catch up”, but even that is too much if there’s another relationship.  

      Why? If you’re not insecure and don’t feel threatened by anything/everyone, then why begrudge your partner’s friendship with a person he has a history with, and which gives him some comfort, in a purely platonic manner?

  17. 17

    Thanks for all your comments re cross cultural dating! Love it!

    I know we diverged from the point of the video (just a bit!), and sorry to hijack the comments , but Evan, if you’re reading, it looks like there’s some interest in a post about implementing your advice cross culturally…😊😊

  18. 18

    I agree with Evan about not putting all your “conditions” out right away. I read all the time men putting a list of requirements, some of which sound quite insensitive and they write for instance “I dont wanna waste my time so if you are not ok with being second to my kids, dont bother me. If you are not ok with me working long hours, dont bother me” etc etc. These requirements are actually reasonable in themselves (anyone with common sense knows that kids and work come first) but listing them right away brings a sense of negativity and bitterness and I never choose to contact or respond to people putting negativity forward.

    1. 18.1

      Hi Ross,

      I just wanted to say great comment! You helped me see something that I struggled with articulating for a long time.

      You said, “These requirements are actually reasonable in themselves (anyone with common sense knows that kids and work come first) but listing them right away brings a sense of negativity and bitterness

      This is so true! Logically I have no problem with a woman saying her kids come first, but hearing it verbalized and shoved down my throat is such negative feeling; especially when this same woman expects me to put her first and make her feel special.

      1. 18.1.1
        Emily, the original


        Logically I have no problem with a woman saying her kids come first, but hearing it verbalized and shoved down my throat is such negative feeling;

        Do you continue to pursue this woman or do you move on? How do you get excited about a relationship in which you know from he beginning you will always be second priority?

        1. Adrian

          Hi Emily,

          Well personally I have never been in this situation. The occasional weekends when I become a single parent allowing my toddler niece and lately my niece along with my toddler and new born baby cousins to stay at my place for the weekends. I now know that though really I love children, I do not want to have any. So I have never dated or tried to date anyone with children.

          But I have witnessed enough men being told this or women mentioning to other women that a “real” man would be able to handle this that I know I don’t like it.

          Emily said, “How do you get excited about a relationship in which you know from he beginning you will always be second priority?

          I wonder this too all the time! After reading Ross’s comment my only guess is it is in the way the woman or man handles letting you know.

        2. Emily, the original


          But I have witnessed enough men being told this or women mentioning to other women that a “real” man would be able to handle this that I know I don’t like it.

          Taking on someone else’s kids is a tall order. If you yourself have kids, you probably understand the sacrifices that need to be made. But if you don’t, you’re being asked to rearrange your social life around children who aren’t yours. You will also have to deal with the ex-partner, an interaction that may be difficult. On top of that, you’d be expected to help co-parent if the relationship became serious.


        3. GoWiththeFlow


          A woman woman who has kids, who thinks that any man should just deal with that fact and go ahead and get involved with her, is doing both herself and her kids a huge disservice.   I appreciate it when men who don’t want to take on kids steer clear of me for dating and relationship purposes.   It’s what’s best for everyone concerned.   If you’ve ever seen a situation where one partner does not want or accept the other’s kids, you know what a disaster it is.

    2. 18.2
      Kareen Loy

      Exactly so Ross.

  19. 19

    I found myself nodding my head at everything in your post, Stacy. I was in the exact same situation. He talked non stop about his ex, she was his “best friend “and he still called her on their wedding anniversary ! He once cancelled our plans on the phone with her right in front of me to take their kids for the night so she could go to the hairdresser. So yeah lesson learned the hard way. I wouldn’t be as upfront as Jonathan but I would definitely observe and try to figure that out. Like you said some guys have no clue about how to fit you into their arrangements with their ex and kids, and if you’re not getting your needs met, bail. My   bf is divorced (no kids) and moved to another state afterwards and doesn’t communicate with her anymore ,   so I knew I had a clean slate.

  20. 20

    Oh Evan! I wish you would ask more questions, interrupt less, and just get more curious. This was so painful to listen to!

    But–from everything you’ve disclosed about yourself, I’m guessing my comments aren’t new to you. 🙂

    You had a guest on your show and you bulldozed him. My ears are still ringing. Thankfully, Jonathan held his own and was very gracious.

    All that said, I do love your podcast and your frankness has helped me a ton. So glad you introduced me to Katherine Woodward Thomas, who introduced me to Marni Battista. Love those ladies.

    Keep up the good work… 😉


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