How Do I Start a Conversation with a Straight Single Man?

Man and woman talking by the pond

I’m a 42 year old woman, newly single. I’m just re-entering the dating fray for the first time in many years, and I discovered very quickly that I have no idea how to identify men my age who are single and looking. They sure seem to be scarce, compared to when I was in my twenties! I’ve chatted up guys who turned out to be gay or attached – they were just extremely friendly/chatty, which I occasionally mistake for an interest in me. And I’m too shy to laugh off any misunderstanding with a comment like, “Well, if you have any single brothers or friends, here’s my card!”

I’m dating online, but I’d also like to meet people in other ways.   Yes, there are the singles events, the frozen food aisle during off-peak hours, etc. But for other situations I may find myself in – elevators, gyms, coffee shops – do you have any suggestions on how I could strike up a breezy, innocuous conversation and still be able to “out” single men?   The “Wow, nice jacket – did your partner pick that out for you?” line doesn’t seem too subtle.

Thanks very much for any insights.

Enjoy your blog, loved your book.


Love your attitude, Linda. It’s tough out there, all right, and the healthiest approach is to do exactly what you’re doing. A combination of online dating, singles events, and real-life interactions, all of which create the greatest number of opportunities to meet single men.

That said, it’s not your job to “out” single men.

Because single men have been socialized well enough to know that it’s their job to initiate conversation with you. And if they don’t, they’re going to go home alone AGAIN. I’m not suggesting that this is a biological imperative or that nothing good has ever come from women asking men out. Still, as a dating coach, I’m a big believer that your primary job is to create the opportunity, not to seal the deal.

Your primary job is to create the opportunity, not to seal the deal.

To sum up, it’s not your position to ask him out. All you have to do is make eye contact and smile. This gives him   permission to come over without being afraid of being shot down. Because that’s every guy’s concern, especially nice guys. We HATE feeling like fools. We HATE rejection. And we’d just as soon not even approach you, since it’s easier to go home and say, “Man, I wish I said hi” than it is to put our fragile egos on the line. The only way to get an insecure guy to come over is to let him know it’s going to be okay if he does.

Rachel Greenwald discusses her proactive approach for women in her book, and my friend David Wygant’s book “Always Talk to Strangers” is also illuminating, although it’s more written for men. But it sounds like you really have two questions, Linda — you want to “out” single men and you want to find pithy pick up lines as well….

And not that I’m any sort of pickup artist, but the best pick up lines are entirely contextual — meaning, they arise in the moment. If you’re plotting your line in advance, it’s likely to come across as canned. Once again, David Wygant gives excellent advice about meeting people organically. Just know that when you’re striking up conversation with a stranger, the stakes are low. Desexualize the situation and just start talking about what’s in front of you and voila — you’re in.

“I always get lost in supermarkets — you wouldn’t happen to have a map to the organic tomatoes, would you?”

“Jack and Coke, huh? Maybe I can teach you to drink it straight.”

Whatever. All of this is the equivalent of the famous party opener, “How do you know the host?” It’s safe, it’s non-threatening, and suddenly, you’re just talking. You’ll learn later whether you have mutual interest.

If he doesn’t show interest or offer to take your number, you’ve got your answer.

So stop being so hard on yourself. Apart from looking for a wedding band, the ONLY way you can out a single guy is to let him out himself. If he doesn’t show interest or offer to take your number, you’ve got your answer. Don’t worry about “wasting” time chatting with gay men or taken men — it’s all good practice, and the more comfortable you get bantering with strangers, the more it’ll pay off when they’re actually single and straight.

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  1. 1

    Homosexuals are a minority in the US ( 10% of the population tops ), so I am curious as to how it is that a single woman keeps running into gay men when in ordinary places like supermarkets.

    Is it a byproduct of living in the city?

    In other words, is it the case that most 40 something men are married, and/or living in the suburbs such that they will not be found in urban supermarkets?

  2. 2

    Taking a wild guess is that gay guys are more open to impromptu conversations than most men. They don’t seem to be as reserved and are more entertaining right from the start; why wouldn’t a single woman feel attracted? Yeah, it sounds stereotypical but it’s a stereotype for a reason.

    1. 2.1

      Or to put it more simply, they don’t fancy the woman so aren’t under any (probably self-imposed) pressure to impress her. They can just be themselves around straight women.

      And we all agree being yourself is attractive.

  3. 3

    Linda, you’re doing the right things as far as creating opportunities. I’m a big fan of joining activity groups and clubs (college alumni clubs, co-ed sports clubs, social clubs, etc etc) and just going out to places where large numbers of people socialize. This includes bars and clubs. Roll with you friends, have a good time, and let guys come to you.

    Evan is completely right with his points. It’s the guy’s job to open you and “out” himself as straight and available, and it’s simply your job to BE available, interact, and socialize. It’s very much like dancing, where the guy leads. Also, I always recommend dressing attractively and putting your best foot forward. Smile, and if you see a guy you like, shoot him a look.

  4. 4

    BULL CRAP!!!

    To the letter writer – take it from a guy you very might be interested in having talk to you….

    I’m 42 – just like you, and I’m single. I’m shy by nature. I am still a pretty good looking guy. I have a better physique than probably 95% of men my age. I’m not bragging…just calling it like it is.

    I’m straight. I’m not looking to get married. But, I am always looking for quality, avialable woman whom I’m attracted to. And yes, I’d take on a monogomous relationship with a quality woman.

    I 100% disagree with some of the advice that has been posted here (hello Lance) that puts you in a passive conversational situation waiting for the guy to initiate, waiting for the guy to ask you out.

    Look, there is NOTHING that would make my week more than to have an attractive woman show an interest in me, start a conversation with me, AND if she asked me out, or just intimated that she would like to get to know me better, I would be ecstatic.

    Given that I am 42, it does not happen like it used to. But I used to have women (strangers) come on to me all the time in public. I LOVED IT when women showed enough inner confidence to basically say, “fuck it, I like this guy and I’m going to show him I want to be with him.” I admired them for it. I did not think they were sluts, losers, feminists, or desperate.

    I’m sick of this bullcrap. This is 2008. Women want equal rights, and I’m all for that. But, when it comes to romance, our society still thinks it’s the man’s job to initiate.

    What happens when women don’t take the bull by horns (no pun intended)? They end up single and lonely.

    My advice is, go for what you want, but do it in such a way that you don’t come off as desperate (a big turnoff).

    Trust me – there’s plenty of attractive guys out there like myself that would LOVE for an attractive woman to show their attraction. And yes, it’s ok for women to start a conversation with an attractive man, and yes, it’s ok for a woman to ask out a man.

    Good luck.

    1. 4.1

      Honest comment, but women (I am one of them) don’t end up lonely and single because they don’t take initiative – they end up lonely because they are  maybe too aggressive, too alpha female, too much of what turns (most) men off…

      I’m only now learning not to approach men (with 0 success and tons of humiliation) and instead simply be open to interactions. That’s when you learn what kind of man you’re talking to 🙂

  5. 5

    Where do guys like you hangout? I’m not adverse to striking up a conversation with someone who looks interesting, but there does seem to be a lack of 40- something men about. At least those without a wife nearby. Where are you guys?

  6. 6

    Dude, BigFella, relax. I’d love it also if girls opened me, but I understand and accept why they don’t. There’s two problems with what you’re suggesting. 1) Not every guy is like you, ie cool and muscley, and in fact there are tons of weirdos and psychos that will take advantage of a woman who is too straightforward or overly nice. You can go on the internet and read plenty of online and offline dating horror stories. 2) It’s your JOB as a man to be the confident one and lead the interaction, this is part and parcel of what creates attraction. Like I said, it’s like dancing, and if the chick leads it’s really lame.

    With that being said, I do know a couple of chicks who have opened guys and made it work just fine. It’s the exception though, not the rule.

  7. 7

    Bigfella, I’ve heard many times a guy say how much he would LOVE it if a woman FINALLY made the initiative for once – but the honest truth is that if the same guy really liked the woman HE’D take the main step. Truth is, a lot of guys are really put off by a woman who is too forward. And women are attracted to a guy who shows confidence, that he’s willing to risk taking the initiative.

    Or he’d think she’s too easy; sure he might be nice and all but at the end of the day he’s probably not that into her.

    Instances when the woman takes the initiative, I’ll bet it was after the guy sent a major signal.

  8. 8

    Some thoughts.

    Available men over 40 are scarce. Maybe they stay indoors, who knows? Every time I see anyone nice on the street, or meet someone at an event – it ALWAYS ends up that they’re attached. I’m hoping I’m wrong about that and they’re hiding out somewhere, but it has been like that for a long time, and I’m a careful observer. When you finally spot one, there’s some kind of catch – they are single precisely because they want to stay that way, or some other factor that would disqualify them from an actual relationship. You really need to have a positive attitude.

    I like Evan’s advice as to initiating conversation. Basically, his entire response was dead on. I wouldn’t strike up conversations just like that, unless it is something very topical like “where’s the nearest laundromat?” Men will take the initiative if they are interested in a relationship, and if a woman is desirable to them. When it gets to the point that you are really working at it – I think the men recognize that.

    Unfortunately for many attraction is just not the kind of thing you can come up with a strategic plan and battle order. If he finds you attractive, he will find you attractive whether or not you have good introductory line. The only thing strategic planning can do for a woman is help put her in a place where maybe she might actually be exposed to a man who might like her. After all, she won’t get anywhere if she stays in every night. But she cannot get him to like her. There is nothing you could plan or say to a man that will make him become interested if he did not feel the spark fairly quickly.

    So if you are in a great frame of mind, positive, and getting out there, just exposing yourself to lots of potential men could possibly do more for you than chatting with random strangers. Sadly, I have absolutely no idea about what to suggest as to where these venues might be. I suppose the next question should be – if you are looking for men in their 40s, where are the events and activities that these men attend? Or is it just demographic – is this the age group where they are most likely to be attached?

  9. 9

    Selena – “a lack of 40-something men about?” LOL – The Federal Government has put all all men aged 40-49 in a pen at Alcratraz.

    Most of us 40somethings are ass-ugly or are married. Probably why you don’t see them about town. You won’t run into many of them at the 21 Club. Most of them are too busy raising families.

    To the letter writer (and downtowngal who missed my point). PLEASE DO NOT assume a guy is not interested in you because he does not strike up a conversation with you or will not ask you out if you have good chemistry in an initial conversation.

    Some guys are shy. Shyness is nothing to be taken lightly. It can be a serious disorder for millions of Americans (and people around the globe).

    And not all shy guys come off as pathetic dweebs as the media might portray them.

    It helps if you can spot nonverbal signs of shyness.

    downtowngal – don’t take this as a personal attack, but you could not be more wrong with your comments. Try reading some good social pshychology by someone who has studied the dating and mating world. You are seriously misguided as to what really goes on out there socially.

    I’ll spare you the details. I’m sure you wouldn’t agree with what I’d have to say about your comments, so if you don’t know by now…

    To the letter writer: I cannot possibly believe that I am the only decent looking, nice male out there who would not fully appreciate a woman who was assertive in going after what she wants romantically. You see, some of us don’t live in the 1950s still. Maybe we are a minority, but I truly believe that you can really get what you want socially if you stop the old-style passive approach.

    The commentary that you have to stand around like some statue of liberty hoping a decent guy will talk to you and ask you out is bullcrap.

    I’m shy, and thank God that some real quality women have probably spotted that I’m shy and have made the move on me. Otherwise, we might not have gotten together. But then again, maybe these women spotted that I don’t think in bullcrap absolutes and I don’t carry around attitudes that women are the weaker sex who needs to sit around waiting for Mr. Dreamy to ask them out.

    These comments in this thread make me appreciate the woman who are assertive with me and who do come on to me (in a respectful way) even more. Who wants to wait for Donna Reed or June Cleaver.

    For the guys out there who think that THE MAN must do all the work -that it’s his “JOB,” all I can do is LOL. It tells me that you are not very socially desirable. For the record, many women noadways are incredibly forward, and can be very aggressive.

    Maybe try a new mouthwash.

    And to all a good night….

  10. 10

    Selena- sorry, I forgot to answer your question.

    I can’t say where 40somethings who are available hang out. No doubt, most are attached. But there are many who aren’t.

    As for me, I’m a lone wolf. I don’t run around in packs. I think that’s another reason why women feel comfortable approaching me. I don’t hang out in guy packs. I’m comfortable traveling light.

    I’ve found that women are forward in all different places. I don’t hang out in bars or clubs. Women approach me in pedestrian “every day” places. So, I’m quite surprised to hear people here say that doesn’t happen. I guess I’ve lived in a different universe.

    By the way, I’m nice looking, but definately not a pretty boy model, and while I’m in great shape, I’m not magazine material.

    Maybe there’s more to it than looks.

    Ladies – we men need more assertiveness out there. Don’t listen to what the dudes or your girlfriends tell you. Go for what you want with the guys. If a guy is so insecure that he feels HE has to take the lead with the woman, he’s not worth it.

    There are guys such as myself who will appreciate your making the first move. And we’ll make it worth your while.

    Li-Ann – great commentary.

  11. 11
    Kat Wilder

    It isn’t just talking to men organically, it’s knowing how to talk to all people that way, male or female, young or old. If you can remove the sexual aspect to it, you become more yourself.

    Then, if he responds, you can add the flirt.

    If you can remind yourself that inside we’re all pretty much the same wanting someone to see us for who we are, and like us for who we are it makes it easier.

  12. 12
    Evan Marc Katz

    By putting it on women, Big Fella, you’re trying to rewrite societal conventions. And most women haven’t gotten the memo. On the other hand, you know what you have to do. You said it yourself.

    “I LOVED IT when women showed enough inner confidence to basically say, fuck it, I like this guy and I’m going to show him I want to be with him.

    So, how about you show enough inner confidence to basically say, “fuck it, I like this gal and I’m going to show her I want to be with her.” Instead of doing what you’re doing now: telling women to break through your shyness because you don’t have the guts to talk to them.

    Hate to challenge you, man. Appreciate that you’re a reader. But the surest path to change is to do something different yourself, not to wait for the world to come around to your position.

  13. 13

    I do not believe in the *scarcity theory* that there are no worthwhile, attractive and available men out there. I am a 41 year old single woman and I do agree it is harder to meet potential mates, then say when I was 21; and I agree with Li Ann that it takes concerted effort and a positive, resilient attitude. However I think it is a matter of really going beyond the surface of what we think we want, and finding out that the guy writing to you on who is 5′-6″ tall actually is pretty sexy in person, or that the guy with the receding hairline is confident and funny, or that the handsome shy guy opens up when you get a couple of drinks in him ; ). In order to find these hidden gems, it takes more “work” than just meeting the handsome fraternity brother at the keg party when we were in college. But I think there is ultimately more depth, and ultimately greater rewards for being open to getting to know a person on more than a superficial level before ruling them out.

    (BTW, I just broke up with the 5′-6″ guy after 6 months; our timing was off, so I am looking again 🙂 Thanks to Linda and Evan and all others for this post; it;s my favorite yet from Evan’s blog.

  14. 14

    Hi there
    I agree with Evan and I can speak from personal experience. Yes, I know it’s a single data point, but here’s my story…
    I’m a 25 year-old pretty attractive gal, e.g. since becoming single, half of the time I’m introduced to a single guy, either the guy asks me out or a few days later the introducer tells me the guy is interested and asks me if I’m interested as well.
    To this date, I’ve asked guys out on numerous occasions. Only 2 of them said yes. One of them was the most painfully shy guy when it came to approaching women. The other one told me it was a nice surprise and that he didn’t approach me before I did because he thought I wasn’t interested in him.
    The others? While some people are flattered by a cute young woman approaching them, they are flattered…at best. I re-iterate, it’s only a single data point, it might very well be the way I approach them that they find too aggresive, in some cases they may not be attracted in the first place etc.
    Nevertheless, I feel guys still would prefer to think they are making the first move. I agree with Kat Wilder in that if you can strike up a casual talk easily, he will most likely send stronger signals if he’s interested. A surprising exception to this is a friend of mine who is model handsome. Girls always woo him, girls always ask him for a phone number. He is very happy and doesn’t think any less of the girl who approaches him first.. probably because he knows he’s hot stuff and is understanding of come-ons. plus he doesn’t need to move out of his comfort zone.
    so while I sincerely wish one day BigFella’s wishful world of pursuer women will be the norm (since I obviously prefer pursuing to being pursued) I don’t see that happening anytime soon.

  15. 15

    Evan – sounds like more than a little sour grapes to me.

    I never said women have to do all the work.

    Women approach me. Not as often as they used to, but they make it easy for me.

    Sorry you and other guys have to do all the dirty work.

  16. 16

    To BigFella,

    I don’t like what you are saying at all. First of all it’s you aggressive attitude that puts me off, second of all it’s LOL in 40% of your comments, you are 42, right? I just thought lols would be left behind by the age of 42…OK, now – I am very attractive and young (31), but need a man and so I go out, but I go out because I like to go out, not necessarily to grab a man. I am also very particular who I’d give my number to, but I am a nice, unpretencious person and talk to everyone. So I don’t care how shy you (men) are if you can’t come up to a woman you like I don’t like you already. A man has to be a man – very simple. I am assertive and forward in a lot of ways, but I WANT a man to want to come up to me. He could be great looking, but if he doesn’t have the guts to come up to me I think “what a loser” – I’m just used to those brilliant, beautiful go getters – everything run/ran smoothly in their empires, not just the ladies aspect. So you are 42 now and still single – I don’t know, maybe the main reason for that is you are too insecure to come up to a really cool looking lady, huh? Thus you limit your chances…It is still a man’s job, no matter what you say.

  17. 17

    I’m 38…lol!

  18. 18

    Victoria -Seriously, for you to call someone else immature. I would guess by your post that you are a teenager.

    For you to think that if a man is shy he is not a real man – that tells me a lot about you.

    Thankfully, there are many, many liberated, sophisticated women out there who do not have such a high school mentality toward the sexes.

    And by the way, dear. There are literally thousands of hot women out there who will agressively purse men they want.

    Like I said, I’m LOL at all this stuff. I have gotten plenty of approaches in my life. And I still get the occaissional approaches from college age girls.

    You see, many women do not hold your views. You can’t tell me otherwise.

    This reminds me of a old friend who kept telling me, “You know the coke commercials where the girl walks past the guy and then turns around and smiles to him? That never happens in real life – it’s a myth.”

    I always laughed inside at his comment. Because many times I experienced that nonverbal signal from women in my life.

    My friend assumed that just because he never experienced it, it had to be a myth.

    Similiar to your argument. You think that just because you and other stone age women will not approach men, then it’s a myth.

    Even at 40 I had young 20 somethings coming on to me. That was my universe. Hope you’re happy in yours.

    It’s slowed down recently, but I’m forever grateful to the women who made the first move.

    And perhaps you didn’t read my former post. I am single becuase I want to be.

    Revenge of the shy guys!!!

    Markus – LOL at our LOL.

  19. 19

    Linda – the best way to start a conversation with a straight, single man over 40 is with “Hello”. After that talk to the man as if he weren’t a man you were interested in, just talk to him like it was an ordinary situation. Evan, as usual, gave great advice. Follow up on every lead he gave you.

    I would like to agree with BigFellas views, but I just can’t.

    I was raised in a family dense with feminists. Even for a man like me, if a woman is too forward in a dating situation, if she “tries to be the man” or take “the lead” as in dancing it just makes me uncomfortable.

    That seems to be the case for many other men out there.

    As Grouch Marx said:

    Who are you going to believe? Me or your own eyes?

    It may be wrong, but Evan is dead on when he advises people to be in touch with the reality of dating rather than what we would like the ideal to be. His point about gauging the your options and the options of who you are interested is valuable.

    I know it sounds bad, but there are many more women who will not be uncomfortably forward, who act like the software I was born with is designed to handle. I will go with them first if I can’t overridde my discomfort. I do try to short circuit that BS, but sometimes I just can’t.

    Linda, Selena et al. If you are ever in the Washington D.C. area and would like to spend the evening with an over 40, in decent shape, single, straight, non-neurotic man please let me know.


  20. 20

    Appears we’ve hit a nerve!

    Again, I agree with Evan’s response. Asking for women to do the opening and “dirty work” (bigfella’s word) is asking to change societal norms, and in fact it’s much deeper and goes against our core programming.

    Personally, I love opening and flirting, ie leading the dance, and I get a real thrill out of it. I used to be shy too, but I changed all that about a year ago. Now I understand that actualizing the male role is very much a part of what creates attraction and sexual tension.

    I’m in my 30’s, so I can’t tell you exactly where the 40-somethings are hanging out, but I suggest do wider online searches. Instead of confining yourself to a 10 miles radius, try 100 or 200 miles or more. Folks in their 40’s have the means to initiate and maintain relationships that are far more distant.

    I met a beautiful American woman based in Amsterdam who was actively searching for a mate within 1000 miles. She was a well-off professional, so she definitely had the means to close the distance. No, I didn’t get with her.

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