Should I Go on a Second Date With a Guy I Don’t Like to Get Practice and Attract More Men?

woman on a date with a guy she doesn't like

Hi Evan, I’m a 29 year old woman who grew up with fairy tales that says “someday my prince will come…” Well, I’m like Sleeping Beauty, happily sleeping. But I think someone set an alarm clock for me. Probably the biological clock. And it woke me up. Well, my prince must be lost somewhere out there. So, I decided I should go meet him halfway and I signed up with a matchmaking agency that set up dates for me. The first few didn’t go well. However, the 4th guy “sort of” asked me for a second date. Right after he said my arms are fat. He didn’t exactly ask me out, but he asked if I have any plans for the coming holiday. He said he wanted to go out to take photos, which is an activity we both have some interest in. Well, I wasn’t prepared to make it THAT easy for him. I still wanted him to ask properly. So, I asked him to call me when the time was nearer to confirm.

Do you go out with a guy who is tactless enough to tell you that your arms are fat on the first date? Of course you don’t.

Throughout the arranged date, I let him talk. I asked questions so that he knew I was listening, etc. I let him lead the conversation most of the time and as men usually are…he seemed to enjoy talking about himself. So, the coffee date lasted two and a half hours. I was smiling and trying to keep the date enjoyable even though he said my arms are fat. However, I really didn’t feel any chemistry with him. In fact, he’s really not the type for me. My question is, should I go out on the second date with this guy (if he asked properly) although I don’t really like him? My friend has a theory that says men like women who are attractive to other men. So, I was thinking if I start dating more, more men would probably come my way. In addition, I would like to learn how to interact with guys. So, even though I don’t like that guy who asked me out on a second date, He’s the only one who has asked me out on a second date! Should I go? Or should I just lose him?


Dear Shay, I’m quite sure readers know the answer to the question: do you go out with a guy who is tactless enough to tell you that your arms are fat on the first date? Of course you don’t. But our readers also know that I wouldn’t be writing you a response if there wasn’t a little more nuance to the answer, so here goes: First, good for you for taking your love life seriously at 29. Most women I meet only start after they hit 35, and find it even more difficult than you will. No matter what happens, your efforts to learn and grow and understand men will be rewarded. (BTW, if you’re 35+, please don’t get angry at me for pointing out that men prefer younger women, thereby making it more difficult for women 35+. That’s not a value judgment, it’s an observation.)

Second, this matchmaking agency set you up with a dick. Now, no one should be judged on a singular mistake. But then, I was supposing the mistake was talking about an ex or telling a dirty joke, not insulting you. “You have fat arms,”is no different than, “You’re boring,”or “You don’t look as good as your photo” It’s an insult, and not even a veiled one. So yeah, dump the loser.

If you’ve been waiting for Prince Charming and have decided to take a pro-active approach to your love life, you’re in for an eye-opening experience.

Except, Shay, you have a theory about being out with a man making you more attractive to other men. I wouldn’t put too much emphasis on that, as most men aren’t trying to pick up women who are on date. But your second point is more valid: “I would like to learn how to interact with guys.”If you’ve been waiting for Prince Charming and have decided to take a pro-active approach to your love life, you’re in for an eye-opening experience. You’ve already got a taste of it. But the way I see it, if Dick is using you (and your “fat arms” for company when he’s got no one else to hang out with, you are well within your rights to use him to practice dating. My caveat is this: if being around him actually makes you feel bad, because he’s rude to you and doesn’t see your interactions as “dates” then, well, he’s useless as a dating experiment. Cut him loose. But the overarching idea, not about Dick, but for dating, in general: it’s okay to date someone who is merely Mr. Right Now, especially if he just sees you as Ms. Right Now. What’s good for the goose is good for the gander.

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  1. 1
    Curly Girl

    Oo, Shay, don’t go out with him! There are better practice dates!!! If you were learning to play the violin it wouldn’t do you any good to keep playing the wrong notes over and over, you need to play the right notes, slowly at first, gradually building to expertise level.

    The only practice you can get here is recognizing a non-starter. Also a good skill do develop.

  2. 2
    Curly Girl

    Just a random drop of joy: My guy is just terrific. He is so gorgeous and sweet and s*xy. We don’t care about getting married (even though we’re both very stable, committed, decent types); he’s a little younger (defying the notion that men want younger); and we’ve known each other for more than10 years, so there’s a great deal of comfort there, along with the hotness.

    I highly recommend this way of doing relationship.

    Sometimes I read stuff on here that makes me cringe, it’s so unloving and useless. Like the guy making the fat arms comment. When you’ve been around people who treat you respectfully you immediately recognize that kind of talk/behavior for what it is–hostile and rejecting and the tip-off that this person is not a candidate for a happy relationship.

  3. 3

    She could be using that 3-4 hours of second date time with a man who is shallow, self-absorbed, and verbally clumsy (if not flat-out abusive) to learn more about men and relationships in general, find a personal shopper to help her learn to dress more attractively and camouflage her arms if that remark really upset her, have a makeover, join some online dating services, have a session with a dating coach, get a mani-pedi so she’ll feel more “all that” — or pretty much any other activity in the WORLD that will help her achieve her goal of feeling more self-assured, feminine and happy, and finding the great guy who will eventually become her husband and father her children.
    Duty-dating is great, practice is great – but when it’s a guy you’re not attracted to and whom you’re kind of dreading going out with again? Seems counter-productive to the larger goal.

  4. 4

    What’s good for the goose is good for the gander….ok? I can get on board with that!

  5. 5

    I’d take this a step further. The first time you are out with someone and they insult you? Say you’ve gotta run, get up and walk the hell out. Standing up for yourself will make you feel better about yourself – you should never tolerate less than respectful treatment, and don’t take it personally. The guy is just an ass.

    I have encountered quite a bit of rudeness in the dating world, and I just don’t get it.

  6. 6

    I might go out with that guy again, if I felt like he was generally tactless and not cruel. I might even explain to him how that made me feel when he said that. I mean, he’s on this matchmaking service, too, and maybe he has no idea what he’s doing wrong?

    Do most women really only start seriously looking around age 35? I was 23 when I got on Match, and probably dated upwards of 50 guys over my 3 years with the service.

  7. 7

    Also, there is no point in “practice dating” on a jerk.

  8. 8

    The first few didn’t go well. However, the 4th guy ort of asked me for a second date. Right after he said my arms are fat


    I counted no less than 3 reasons why you should NOT go on a second date with him in that quote. If you are sure you aren’t him, that is all of the reason you need.

    As an interesting *aside* I hear complaints from women all of the time that 20 something “men” don’t come right out and ask women out. I am a few years older than that generation, but aside from being able to eat peanuts, doing long division by hand, not texting and calling a woman, on the *phone*, I also know how to treat a woman.
    So, I was thinking if I start dating more, more men would probably come my way.

    That is true, but it will only work finding you a man you like, if you stop dating the ones you know you don’t like.

    Be nice to the dumbass who lacked the social common sense in telling you that you had fat arms. If you go on a second date with him he might just get his hopes up and then get disappointed.

  9. 9

    @Ruby, post #5.
    Exactly, there is no reason to tolerate BS like that on a date. I would have told the blockhead that he was being offensive as a public service on the off chance he really didn’t know, then I would have gotten up and left.

  10. 10

    Your date sounded like an ass – I wouldn’t give him a second chance – why torture yourself? I just want to point out that matchmaking services are just SCAMS. I joined a very expensive one a few years ago and it was the biggest mistake I ever made (money-wise). In the beginning they set me up with a few totally sub-par men, after promising me great things to get my money. They occasionally send me references, but the guys never call me. I don’t feel like going out of my way to meet sub-par men, so I don’t bother calling them.

    My point is – Ladies, please don’t join matchmaking services! They are preying on your insecurities and are just out to get your money. What kind of men do you really think join those services? Socially inept, desperate, ugly, and otherwise not successful with women. No, there aren’t any handsome doctors out there who are just too busy making money or saving the world to meet Ms. Right. Invest that money in yourself instead – so you can feel better about yourself and meet more decent men on your own in the real world.

  11. 11


    Are you considering dating sites “matchmaking” services? Or do you mean actual people who set you up? (Love’s version of the headhunter).

    Because I can tell you- if you’re a person who’s not into the bar scene and are only into activities that attract primarily women (ie, art, culture, etc.) the internet is often the only option.

  12. 12

    I’m talking about actual matchmaking agencies. They charge a lot of money and don’t really deliver what they say they will.

    I’m all for the internet dating sites, though I’ve become somewhat disillusioned with them lately. They don’t charge anywhere near what a matchmaker does, and there are even free sites. I know people who have met their significant other this way, so I feel it is a good method to meet people. I’m now trying to meet people in more traditional ways, like through friends.

  13. 13
    Mikko Kemppe - Relationship Coach

    I probably would not go out with him either if I was her. Although, I am little curious how exactly did he say that her arms are fat and in what kind of context?
    But I think there is a lot to be learned from this experience. For number one, I think she did one of the most common mistakes many women make on a date, which is this: trying to be a good date by being a great listener.
    Often unfortunately the more you ask questions, show interest, and be a good listener on a date with a guy, the result usually is that he just becomes more and more self-absorbent and only realizes how interested he is in himself. From a guys point of view, he is often just as innocently trying to be an equally good date by giving great answers to your questions.
    Much better idea is to interrupt a guy politely if he talks too much on a date and start talking about yourself instead. This way, he will get to know more about you and become more interested in you instead. This way you will have created a much better environment for finding out if there is chemistry between you two.

  14. 14

    Curly Girl said: Sometimes I read stuff on here that makes me cringe

    Same here. Occasionally I read these letters and can’t help but think, “oh, so this is what actual problems look like…”
    All my negative dating and relationship experiences seem laughable in comparison. 😐

    I disagree, though, that in order to discover what loving and respectful treatment looks and feels like, she has to spend more time around the people who give it to her. First and foremost, she has to work on herself – her self-esteem, for starters.

  15. 15

    I have a male friend (well, he is actually the older brother of a friend) who keeps using these matchmaking services with absolutely dismal results. I mean, he tells these positively jaw-dropping stories about his dates sometimes, after which we are all, like, “where do you FIND these people?!” 😮

    So, anyhow, once I asked him, why he uses those matchmaking services in the first place. I just pointed out that I have never encountered a quality individual who would resort to that (there is nothing wrong with the man, except for the accumulating desperation; and, in my opinion, he puts up with a bit too much crap), which automatically tells me something about the quality of people who do. And women, no less! I mean, ordinarily women are inundated with responses on the dating sites, so what ever would possess a woman to pay [however many] times more for a matchmaking service instead??

    He said, it’s because a matchmaker can provide a selection of potential dates that is tailored to his specifications, and online he has to do all the work himself.

    Well, until I see a successful result, I am not convinced.

  16. 16
    Evan Marc Katz

    I just decided. I’m gonna write a blog about matchmaking. Gotta be careful not to burn my bridges. I’m speaking at the Matchmakers Conference in New York next month…

  17. 17

    I’ll tell you why I joined the matchmaking service: I was feeling hopeless and desperate after just being dumped by my boyfriend. They got me at a very vulnerable time with high pressure sales tactics and I really wish there weren’t companies like this around. They totally took advantage of my situation. I think they change their company name every year to avoid BBB exposing them (though they will claim to have been in business since the 70’s.) Since I can’t get my money back I am on a bit of a crusade to protect others from making the same mistake that I did.

    I’m totally embarrassed by it, that I got taken like that. I’m an intelligent and attractive woman. I just suffer from a lot of self esteem issues when it comes to dating. On the upside, the experience did make me stop and look at myself and say, “What is wrong with me that I do insane things like this for love?” I then started therapy to get to the bottom of it. At least I now understand why you need to love and accept yourself, not only when dating but in everything you do.

  18. 18

    “No, there aren’t any handsome doctors out there who are just too busy making money or saving the world to meet Ms. Right.”
    Listen, I’m as cynical as the next guy, but there are plenty of people who are just too busy to play “the singles game.” When your premise is that far off, anything you have to say about “SCAMS” is not incredibly trustworthy.
    There are plenty of guys who will “play ball” with a matchmaker or on a dating site to get the women coming their way, but are really either kind of antisocial or play mind games (note to pickup-artist haters or confused pickup-artist wannabes: “your arms are fat” is not a “neg,” it’s an insult). Report him to the matchmaker so he’s given the heave-ho. To Shay: the best thing you can do for society and yourself is to make sure this dipstick knows comments like that are unacceptable and the reason you’re rejecting him.

  19. 19

    Seems OP’s example doesn’t really answer the question titling this post. He insulted you and sounds as if he didn’t exactly ask you out on a second date properly, so don’t go. If a guy likes you, he would want to try hard to impress you, not insult you.

    A better example would be a guy who treats you well but you didn’t feel a lot of chemistry on the first date, so should you give him another chance? In order for the ‘multiple dating theory’ to work, you have to feel positive energy. But if you’re already feeling negative, this can make you feel jaded, which will rub off on other guys.

    Only date if you feel good about yourself. Better to take a break after a string of bad dates and do something you enjoy than wallow in negative energy.

  20. 20

    There are good matchmaking services out there; but you need to really check references before you sign up with one. If a service won’t give you a list of people you can call on the phone to ask what they thought of the service, then that isn’t a service you want to use.

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