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. 61

    I didn’t think you were attacking me JuJu. I rather thought you were under 30 and trying to make a case for age and eligibilty being unrelated. To that I disagree–meeting single men and women when you’re older IS more difficult than when you were 20.

    Other than that, I tend to agree with you.

  2. 62

    “Believe it or not, I’m not going to directly jump into the fray that seems to be occurring. ”

    Why, Verbosity? Other than to live up to your name?

    In one of your other comments you mentioned that you were going to always, always, always remain single. (Notwithstanding the degree to which your personality itself might be an outstanding relationship repellant. But I digress.)

    As a result, what could you possibly have to say to people that want to be partnered?

    Or are you just “inserting your masculine energy”, as David DeAngelo puts it? Waving your wand at the world in a desperate, panting attempt to insure it knows that you exist?

  3. 63

    to juju/selena,

    ..weren’t you two ever told, that, one of god’s biggest jokes, is to allow women to go through their 20’s, just to keep this planet populated?……some women, have to think this way, just to maintain their sanity….

  4. 64

    No hunter, I’ve never heard that. Though I did spend my 20’s raising a child, so I see the irony in it. Actually, the only thing I really miss about my 20’s is my unlined forehead.

  5. 65

    This is for M. I’m not going to fight with you on off-topic matters. It is nonsensical and a waste of everyone’s time, particularly when I’ve said nothing to you in provocation.

    Contrary to what you asserted (“In one of your other comments you mentioned that you were going to always, always, always remain single.”), I made no such statement whatsoever. I have said I see no legal reason to marry, but that is another subject, and stated in another thread, I believe.

    If you wish to pick a fight, that is your choice. However, at least make a minimal effort to be accurate in your paraphrasing. Do not make something up that does not exist. I, for one, will respond no further to you.

    Best of luck to you.

  6. 66

    Single women over 35 should:

    1. Take up dancing. Lots of single men show up at ballroom dance classes, contra dances, and so on. Try to find such men in your area, or just go to a free event in your area. Although some classes/events may require you to sign up with a partner, you can go contra dancing by yourself (it’s not technically a partner dance, since everyone in the room ends up dancing with everyone else in the room), and lots of single contra dancers marry people they meet through contra dancing.

    2. Put your best foot forward on your online profile, but don’t put all your eggs in the online dating basket, as the odds are stacked against you in that particular venue.

    3. A book I read did an actual survey of women leaving a marriage license office, asking them how they met their spouses. A whoppingly-high percentage of engaged women over 40 met their mates through some sort of health or sports club activity, so definitely join a (friendly!) gym, ski club or other activity like that. They are often informal singles meet-and-greets, or have events that basically function as singles get-togethers.

  7. 67


    I am a shy person too, to the point that I even have trouble making eye contact with men I find attractive (a real stumbling block, since eye contact is really one of the best ways a woman can provide a man with an “opener”).

    I don’t think the world is going to change any time soon to make it easy on us shy people to socialize with ease and start relationships. We live in a society (even a world) that is very extrovert-oriented. Very assertive people are admired and even seen as superior or more competent in their jobs, more attractive in their personalities, etc, than introverted people. It doesn’t mean us introverts have to change who we are (not possible anyway) but it does mean that since we are living in a world that is not really friendly to us, we have to *adapt*. Adapting is what makes humans so successful as a species, able to survive in all sorts of climates. By refusing to adapt, you are minimizing your opportunities to relate and/or mate. That’s nature’s way of deleting you out of the human gene pool.

    Shyness is not an easy hurdle to overcome. I know. I am doing hypnotherapy to try to overcome my shyness, and it is starting to help. It is cost-effective, and you will see results quite quickly (especially compared to other more traditional “talk” oriented therapies). I highly recommend it. I think it would really enhance your dating life.

    If you can’t do any of the above, then perhaps you should ask your friends to fix you up with women they know. This hasn’t worked for me, as my friends either ignored my request or told me point blank that if they knew an attractive guy my age, they would be dating him themselves, and would not fix me up! LOL But seriously, look around at your social networks, and see if there are any likely matchmaker-candidates. People who are already engaged or recently married are usually pretty gung-ho to fix up their single friends, and this can be an easy way for a shy person to meet someone new, with minimal risk (especially since your date has to be nice to you and polite, given the whole mutual-friends situation…)

  8. 68

    Hey all, I just want to say I only recently discovered this blog, but I am completely addicted and I appreciate incredibly the honest, sincere, and enlightening comments all you write – that includes Steve, Lance, Marcus, J, Selena, verbosity, Li-Ann and so many others…Just want you to know that all your thoughts are appreciated and Ive learned a lot from you all.
    On a side note, why arent some of you men in Europe? Boy, I miss Americans.

  9. 69

    Evan and to the lady who asked the question.   Today, I officially passed my “flirting” test.   How did I do it (I thought I had forgotten :o).   Standing in line to buy a coffee and just behind me a really gorgeous man.   So I went into practice, “hey.   What are you eating?” etc. etc. and guess what?
    The guy invited me to his table where there were four other guys.
    As I was, I had to go back upstairs to work but it truly made my day and I think the guys enjoyed it too.
    Simple stuff “Hope you enjoy your pancake” (or whatever).
    Yes, the men are supposed to do this.   But what the hell.  

  10. 70

    i completely agree!   Finding a single man over 40 who isn’t single because he has countless issues is nearly impossible.   I struggle with the castrated version of the male species that the feminist movement has created.   Yes, we want you to acknowledge emotions but holy ***** i still want a real man.   If   he isnt brave enough to talk to a female, he probably won’t stimulate anything else either.    The alternative is the self proclaimed alpha male who generally believes himself superior to women and sees us as an inferior species who needs to be saved, guided, rescued.   Where are the confident, healthy, balanced men who are looking for a partner willing to build a life together?

  11. 71
    wander about

    42 and looking – good luck, Many men are no longer on the market – they have gone MGTOW and could care less if you are available or not – It is a fool’s game to go into a LTR today with the way the system is racked against a man.

  12. 72

    This article’s nonsense.

    Why shouldn’t a woman make the first move?

    As I can I can tell you plenty of times I’ve liked a girl but been to shy to approach her and in my 30s I’ve yet to spot the “she’s looking at me” trick. I’ve spotted others but this one is totally lost one me.

    So sure if you like a guy make it more obvious. A guy has to.

    1. 72.1
      Evan Marc Katz

      How about you stop being shy and ask out women, instead of complaining they don’t ask you out? Problem solved. Change yourself instead of trying to change an entire gender.

      1. 72.1.1

        I do, obviously. I’d otherwise have spent my entire life single.

        My point was we’re supposed to live in a world of equality, yet dating is massively unequal. Women are allowed to be/sometimes expected to be shy.

        Women should be expected to make some effort in speaking to guys too. Straight men, gay men, gay women have to do it.

        When a girl hits on them many guys love it too. I do, when it occasionally happens.

        Sure it’s part gender, it’s also party how society works. Guess what societal changes happen all the time.

        That’s why this article is nonsense (and sexist), you’re telling women if they like someone to do absolutely nothing, aside from some vague eye contact and smiling, and he will just know somehow.

        Guess what, he may like you to but have no idea you like him. Because a dating coach has told you to do… nothing of any measure.

        Of course it’s the woman’s role, it’s the man’s role, it’s everyone’s role to be an adult and ask someone out if they like someone.

        Sorry to say but this article reads like it’s the 1900s.

        The second point was general about the eye contact thing not working on all guys. Maybe the women who I have ended up dating have used it on me. Pass. I’ve yet to spot it.

        So for me at least it’s a useless tip to give. And I doubt I’m the only one.

        p.s – Great dating coach skills you’ve got, badgering people. Thanks for that.

        1. Evan Marc Katz

          You’re the one who’s complaining that he’s not doing well with women. I told you how to do well with women. Your response: it’s women’s fault, they should change, they should approach, they should ask me out. I’m a reality-based dating coach. If your entire worldview is that everyone else should change to make your life better, you’ll continue to struggle in whatever you do.

          Good luck finding a dating coach who thinks it should be the woman’s job to ask you out because you’re too passive/shy/afraid to do so. Everyone will tell you to buck up and take a chance on a girl who smiles at you. I wish you the best of luck, but railing against women (and coaches for women who encourage them to smile and flirt, but not ask you out), is a waste of your energy. It’s much easier to just say, “Hey, I had fun talking to you. Can I get your number?” after you’ve had a nice conversation. Your response seems to be that SHE should GIVE you her number even if you didn’t ask. You know who does that? Desperate women and masculine women. There’s your dating pool if you play this passive wallflower role. Enjoy.

        2. Bradavon

          Agreed on the reality front. I’ve no problem with asking a woman out (I never said I did incidentally).

          I do find arbitrary gender definement rather outdated though. Society is always changing.

          It’s absolutely the right to be aware of how society works today, of course, it doesn’t mean you should exclude other successful approaches too.

          You’ve still not explained why you’re so against women taking the initiative too?

          Is it because you don’t think they’re capable of it perhaps? “Not their role” is a rather weak argument to use.

          Especially as surely the whole point is for people to get together, no matter how this was initiated.

        3. Evan Marc Katz

          Putting words in my mouth, man. I didn’t say women are “incapable” of it. If anything, I’m saying that they shouldn’t HAVE to ask out men, because most men got the memo back in third grade that if you like a girl, it’s your job to let her know. Pull her hair, tease her, pass a note, tell her best friend. Men have ALWAYS initiated contact. So to suggest that because we’re an equal society and more enlightened that you should stop approaching women because they CAN approach you? Not really working. Remember, most women WANT to be approached. They don’t want to have to hit on you. And, for the most part, they don’t. Because the majority of men who are interested in women approach, ask out, plan, pay, follow up, initiate sex, ask for exclusivity and propose. So just because a woman CAN do all of them doesn’t mean she ever HAS to do any of them. You are entitled to not like how things work and say they’re unfair. Okay. Meanwhile, all the guys who take the proactive (traditionally masculine) role in dating are doing better than the guys who take the passive (traditionally feminine) role in dating. You can do whatever you want. But yes, I’m defending traditional gender roles that people are widely accustomed to. You’re trying to change what women want – a confident leader, not a passive follower waiting for a written invitation from a woman. Sorry, man. I understand how you feel. I just don’t think your approach is all that realistic or effective. So why defend it?

        4. Bradavon

          Points taken, not entirely agreed with, but points taken.

          Have you heard of the dating app Bumble?

          It, in it’s small way, worked on entirely by women, is shaking things up.

  13. 73
    In Not Of

    Just don’t be surprised if she takes you’re waiting on her to initiate as lack of interest. Why chase after someone who’s lukewarm?

  14. 74

    Two comments on this.   I live in the DC Metro area, where the social norm is you do not socialize with strangers.    You do not even make eye contact with strangers. If you do people look at you like you are crazy and they do not respond back if you say hello or good morning.    It’s bad.   So sadly,   a lot of your advice is not going to apply in this area.   It is very difficult.    People are downright rude and snotty if you speak to them.   Second, if a female is particularly attractive often times, the smiling the looking the eye contact they just do not work. Online dating is really the only option, or going to events like speed dating or singles events where you know that is the reason everyone is there.

    1. 74.1

      I have lived on 3 continents in dozens of cities, small towns, and even a remote village in a 3rd world country with no electricity or running water (really). In every case people were as nice to me as I was friendly, approachable and nice to them.

      I can also attest that there are indeed universal rules that seem to stay the same everywhere you go. One of those is that men are hardwired to pursue. It just is. It doesn’t mean they never appreciate a women who smiles, drops hints, or whatever. But they want to pursue. There will always be be women who want to be the pursuer but they will likely end up with a certain type of man. which is fine if that’s what makes you happy.

      Lol Evan “pull their hair, tease them, pass a note.” Weren’t those the best years of our lives? How easily we forget how simple and natural flirting is and make it something so much more complicated than it needs to be because as adults we started overanalyzing everything to death. We knew when a boy liked us in the 3rd grade and if we get out of our own way, we certainly know now.


  15. 75

    Evan, I feel very conflicted about the OP’s post, as it seems that she wants to connect with cute guys out in the world.   As a single, successful 40-something man, I no longer approach women in public.   I used to in my 20’s, but in the last decade I’ve read a lot about how unsafe and harassed women feel today.   I have female friends who say, “I can’t go to the gym without getting hit on by ten guys.”   They say the same thing about the grocery store, the post office, driving down the street, etc.

    I want women to feel safe in society, and – even though I’m polite and respectful – they don’t know who or what I am.   So, when I go to the gym, I work out and go home.   When I go to the store, I buy my groceries and go home.   I no longer flirt with, ask out, or talk to women in public.   Hell – I don’t even really look at them much anymore, lest they catch me looking.   I do fine with online dating and friends of friends, but because of the pervasive fear women feel today, I just leave them alone in public.

    1. 75.1

      I feel this is a sensible position. I have a lot of   female friends tell me similar, and how much of a drag it is. I went to the beach with one of my good friends last week and 3 guys tried to start ‘conversations’ with her on the train journey there (its under half an hour on the train). For all they knew I was her boyfriend as well. Imagine what its like when she’s alone. Just stick to Tinder guys, its how everyone meets now anyway.

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