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. 41

    …men gather at hardware stores, auto part stores, car swap meets, at raceways, car shows, football games, coffee shops(usually early, in the morning, for breakfast)…….

  2. 42

    J, Selena;

    Thanks for the nice compliments 🙂

  3. 43
    Hadley Paige

    Selena writes: You 40-something single guys still haven’t shared WHERE we might run into you. If you’re not in bars, clubs and we’re missing you at the grocery store, then where should we go?

    My suggestion>> I crew on a racing boat out of Greenwich, Ct. Being in the sailing community for a while now, I can tell you based upon my observations, the demographics for women of a certain socio-economic class would very attractive. In my neck of the woods, the sport is overwhelmingly populated by men (97%+); who for the most part are educated and professional w many quite well to do. These big boats (I crew on a 47ftr w a crew of 8) often are short of crew and would be happy to take on people who would like to try out the sport.

    The races take about 3 hrs and there is generally food and wine after the race either at the club that hosted the event; or on the boat w the crew. It’s very civilized & charming and the conversation flows quite easily. I am sure that women who would ordinarily attract this type of man would do well int his environment.

    If you are interested in checking out the scene, you need only call up your local boat club, tell them you are interested in checking out the sport. They will likely put you in contact w captains who would be happy to take you aboard for a race and see how you do. Once you have crewed a bit you’ll meet lots of men from the other boats at the club. (suggestion: keep to the bigger boats w larger crews)

  4. 44

    You let “J” go on a 5 paragraph attack rant but won’t allow me to respond.

    Just as I suspected, “J” is your girlfriend (or boyfriend).

    It’s your little puppet show.

  5. 45

    Many of the more popular internet dating websites is packed with young singles that are searching to make a permanent match, or searching for fun and sex only. Those singles that are a bit more mature are no longer into pretenses and games, and are typically searching for some comfortable and reliable companionship. Most seniors searching to find their happiness on senior dating website are successful.

  6. 46

    I don’t have any affiliation with anyone else on this message board – not Evan, nor Selena. Evan already has a very cool, intelligent, and savvy girlfriend (loved her article, btw, Evan – especially the part about “mulligans”!) who he seems to be very happy with and has no need to be dating me. I am female and straight, so I am nobody’s boyfriend either. Neither am I anyone’s puppet.

    You certainly have a right to dislike or disagree with my post, and yes, it probably was way too long.

    Though I still stand by what I said and MY thoughts and feelings based on what I read and on my personal experiences – no one else’s. Though I do get great perspective from the blog, from Evan and many of the other posters. And that does sometime factor into what I write.

    Am trying to be more succinct after leaving epic-length comments and posting part of an article twice in succession by accident.

  7. 47

    Just got a chance to read some comments I missed.

    Thank you for the suggestions and perspective, Steve! Very good advice and I will make sure to take it either the next time I venture out, or the next time am feeling really good about myself and willing to take a chance – whether that is in person or just making initial contact with someone who seems awesome online. And to work on having more of that mindset.

    Am currently just working on liking and loving myself a bit more and getting it more together with my job situation, and continuing to learn so that I know I am in a really good place, thereby giving myself a bit more chance at creating something successful and lasting that he too would want to hold onto -whomever “he” might be. Nothing ventured, nothing gained. And you are most welcome. : )

    Yes, I know it isn’t easy for you all either – why I always write thank you notes (via email) and do my best to be kind if someone isn’t for me and make sure it sounds like it is me not him – though, it is usually, both of us – since it takes two to make or break anything or to be compatible. Actually just read a piece on the Empathy Belly yesterday – almost sounds worse than being pregnant ; )

    Even at 36, my neighbor’s great Pyhrenese, Hadley, is one of the huge joys in my life. She is very uninhibited about showing how much she loves you and is a huge sweetheart. You can’t have a bad day when she is around. Can find happiness in little stuff, and it carries you through.

    Also agree with what you posted most recently as well, Verbosity, and appreciate your sharing more of your personal experiences. I look really young for my age too – if I read that right : )

    Lance – aww, thanks ; )
    I’m a Taurus (I’m sure you could have guessed), write about the beach more than I walk on it (though that is nice too), lived in CA – though the only surfing I have done to date is on the internet, I love vintage jewelry, history and learning things. Also, helping people (I bake cookies and pumpkin bread to give away, though not PollyAnna by any means). Also love a guy who has a way with words and who expresses himself well in thoughts and actions (this is reciprocal). Flirting is fun.

    I didn’t see your other comment BigFella – about where to look for single men of a certain age – before you told me I have issues, that I have wasted my life, and other things – it has merit too and I also appreciate you sharing where to meet men.

    Everyone has issues and baggage – the key is how we each deal with our own and finding someone else who is ok with ours and who is dealing with his or her own baggage more or less successfully and has issues that you yourself can understand and be okay with.

    Thanks to all of the guys who shared here and gave their thoughts as well as ideas on good places to meet and interact with men.

  8. 48

    Cool idea about volunteering to crew, Hadley. : )

    I might have to use that in one of my books since I myself get seasick. Great idea though and not one I would have thought of.

  9. 49

    No affiliations email was to BigFella – in case it didn’t follow right after his post

  10. 50

    Re: Verbosity and not a slam at J –

    “Personally, I think it is a terrible idea to date someone separated (NOT a slam at J, just opining) because they often haven’t dealt with the issues surrounding their current breakup mentally. That can only spell trouble for the non-separated person.”

    No worries, Verbosity – I in no way took your comment that way. Nor would I have. Partly because of how it was worded, but more so because I learned that lesson the hard way. And I happen to agree with you 100%! : )

    I always felt that way, and only broke my rule and dated a man who was separated and had (supposedly) filed for divorce after agreeing to correspond with him, against my better judgment. I was at a low point in my romantic life, (one of only a couple, fortunately) and he was oh so charming and seemed oh so into me.

    Maybe he was, maybe he wasn’t. I think it was more about seeing if he could get women to want him (at that time) – not just physically, but emotionally as well. To test the waters and build his self confidence without investing himself until a later date. It seemed very real at the time as did the hate male he sent me saying that I imagined the whole relationship. I didn’t imagine some of what he said, but clearly believed it because I wanted to. In hindsight, was way too early for that stuff to be said and have true validity, and even if he had been genuine, it would have been too soon for him to know his own mind.

    I fell for stuff like, “You are so warm, I bet you don’t even own a winter coat – because you don’t need one.” UGH!!!! Did I mention I was at a real low point? ; )

    And you are totally correct, it didn’t benefit me. Maybe it did him, maybe it didn’t. Only time I have really felt screwed over in a relationship, but even then, I had to acknowledge my part in it. And I did.

    Thanks again for the perspective, Verbosity.

    People who are separated are truly unavailable – no matter what they might think. I still get sent men who state Separated on their profile – shows up in the thumbnail, but I don’t open those, no matter how good they might look.

    I’d say they are off the table for consideration if you want a chance at having them for good. Until maybe 6 to 12 months after the divorce is finalized. But that is just me.

  11. 51

    Damn, I miss boats Hadley… What kinda boat? My personal fave is a Hinckley Sou’wester (Sailing). I need to get outta the desert, which is overrun right now!!!! Damn Super Bowl/golf people 😉

  12. 52

    Here’s my take on it…Evan’s advice was great. If it’s men like BigFella that love it when women make the first move…I may never speak to a man first again 🙂

    In all seriousness, you seriously devalue any merit your comments may have had when you speak in absolutes and are rude and obnoxious about it. Nothing ‘1950’s’ about that. What good is taking the time to make a point if no one will listen because of the way you delivered it? Sounds like a waste of time to me.

  13. 53

    Oh –
    Woe, Big Fella, is me.
    Pick a post to apply it to. ; )

  14. 54

    Ooh …
    Woo, Steve, is you … : )
    and me too someday when I get the guts to take your advice (comment/Post #34)

    Sounds like, Woo hoo, too.

    If being so hasn’t paid off lately or quite in the way you’d like, I think it will soon.

  15. 55

    Verbosity – really got a lot out of several of your comments here – particularly #34. Particularly the dancing and stepping on toes part.

    For me, the dog thing is a touch more tricky. Because a woman may very well come over and show interest in your dog so she can then show interest in you. And I am sure this does happen a lot. Pets can be a good way to get closer to someone or to make it easier for either of you to make a move.

    Though if you do get to the canoodling stage in any capacity – snuggling on the coach, kissing, or doing the horizontal hula, the pet can then start to get in the way a bit ; ) Especially if said pet has attention deficit – i.e, feels he or she has a deficit of attention (being paid to them).

    But some of us are also very drawn to really cool dogs and puppies – I have been a devout dog lover since I was little and they are still a huge pull for me if the dog seems to have a good personality and even more so if he/she happens to be soft or fuzzy or love attention.

    I take pride in that animals – particularly dogs – and elderly people seem to like and trust me for the most part. And take to me.

    Perhaps that makes me sound immature to some, but dogs (as well as my dear, older friends, relatives and acquaintances) have made an appreciable, positive difference in my life, especially during some difficult times. Being able to make an animal happy so easily is a nifty thing in my book. Senior citizens too. Or anyone, for that matter.

    Being able to make people laugh or bring them a little bit of joy, expected or otherwise is also real kick in the pants and worth taking some risks to accomplish. Sometimes otherwise is more fun.
    Aside: Is it really gay guys who own most of the toy breeds and smaller dogs? Have known straight and single guys with kinda frou frou type dogs – I have one as well (Shih-Tzu), so not judging. Honestly curious what ya’ll think.

    I guess focusing on the action and possible reaction – as it relates to how it might make the other (in this case, a man who catches your eye/interest) feel, instead of focusing on the potential end result for you, may be the key to making more women make a move. I think it would work for me, in any event.

    And as several of you have said, it can be a good experience for the asker too – even if they don’t “get the guy” or if he doesn’t get you from the get-go. : )

    Everyone (or most everyone?) wants to feel appreciated, valued, and important. In all kinds of situations. I agree with you all that men want, need, and deserve that too – sometimes I think it is easy to forget that women have the power (maybe ability is a better word) to grant this to a guy by making the first move or by paying a sincere comment, or as Hunter said – by smiling – especially if at him – or making eye contact.

    Even if it did/does go nowhere, you still may have made his moment by paying interest without him having to do something first.

    Very good, “Verb”, and interesting point, about some men being clueless about reading the signals and about being direct.

    Reading the signs is a very good idea for all of us

    I think I’d be more likely to think he was getting it but not interested if he didn’t respond in kind. That would be due to lack of confidence on my part unless, or my low expectations prior to the contact, unless it was seriously obvious he was blowing me off. I’ve had that happen too. Then you just don’t let it diminish you or the fact that you gave it, and him, a fair shot.

    I think many people (me too, sometimes) see what we either want to see or what we expect to see (be that positive or negative) rather than what is before our eyes. Can be tough to read someone you don’t know, especially if you are judging someone either by “their cover” or doing the flipside, and assuming they are an “open book”.

    Reading is Fundamental : ) [Some of you of a certain age will recognize the borrowed credo – which I also subscribe to). Now, if we can more often than not … put the fun before the mental (paraphrased from Swami “Beyondanda” – if you like puns with a philosophical punch, check him out!)…

  16. 56

    Oh, Linda – what a minefield it is! But lots of good advice in these posts. I expect you already do this, but volunteering is a great way of meeting nice, interesting people if you’ve time to spare. Again, if your schedule permits, the same could apply to extension/evening classes. If you pick the right subject (obviously, it’s got to be one you’re at least curious about). Grassroots campaigning? Any social context where communication’s natural and necessary may provide opportunities – e.g. Hadley’s suggestion about crewing; learning another language.

    As for signalling interest. Well, nothing wrong with eye-contact, followed by a smile. If he’s equally interested plus available and on the lookout: he’ll respond. If not, too bad – and you won’t feel foolish or damage your self-esteem (what’s wrong with a simple smile?! At the very least, it’ll make you feel good). As Evan says, men really are socialised to take the initiative; but your smile will provide the encouragement some men need.

    Good luck, Linda!


  17. 57


    Quit writing about my dog’s behavior! 😉

  18. 58

    I don’t think that meeting men (or women) at age 30 (or thereafter) is more difficult than at 20 because of their reducing ranks or one’s diminishing attractiveness. I believe it’s because one knows oneself significantly better by that age and can also SEE a lot more than they could at age 20.

  19. 59

    Uh, I’d venture a MUCH larger percentage of 20 yr. old’s are not married JuJu as compared to people 30 and beyond. Also, there is a much greater proportion of people in college and nite clubs under the age of 30, traditional places where people in that age group meet. That’s what I SEE and yes, I do know myself significantly better than when I was 20.

  20. 60

    Don’t get so fired up, Selena, I am not attacking you. 🙂

    My “target audience” is perhaps slightly different – men under 35 – and there are PLENTY of unmarried and childless men in that age group. I am not feeling the scarcity yet.

    But I was referring to something else. Have you noticed that with age your standards… well, maybe not so much -rise-, but get much more honed? I know fully well that I wouldn’t have even -considered- now some of the people I dated at 18-20, when supposedly I was more attractive simply because of my youth.

    That’s what I meant.

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