Wise Guys: How Should a Woman Pick Up a Man in a Bar?

Advice from three of our guy friends. This week they answer the following: What are the best ways for a woman to pick up a man in a bar?

Gay Single Guy (Daniel): Well, what kind of bar is it? If it’s a sports bar, talk about the game of course! I’m going out on a limb here as a queer man, but most straight men lurve women who are into sports. And why is that? Because it’s a pleasant surprise that keeps giving pleasure. Imagine meeting someone attractive that happens to share an interest with you that you can talk almost endlessly about. Wouldn’t your heart just melt if you met a genuinely straight guy who loved shopping for clothes and talking about it? It’s the same kind of surprise and euphoria for a woman and sports! But outside of the sports bar, I know the absolute best way: walk up to the man and offer to buy him a drink. Why is this frakkin’ brilliant? 1) Totally unexpected; 2) Demonstrates both a cleverness and a sense of humor; 3) Shows independence and adventurousness; and 4) It’s also an open door to a smart discussion on male-female dynamics, role-reversals, feminism, etc. See, it’s perfect!

Straight Married Guy (Figleaf): You’d think the best way would be to ask for his phone number and say, “Can I call you later.”  Unfortunately that seems to make men nervous if they’re not already pretty interested.  That’s not as unfair as it sounds, though, because chances are good that unless you’re already pretty interested, it makes you a little nervous when men try to pick you up!  Here’s what I’ve seen work pretty well no matter who’s asking: make or permit eye contact without making a big production out of it.  Then go back to doing what you were doing before.  Try for eye contact again every now and then.  Smile back if he smiles.  If he seems interested, find your way over to him (if he doesn’t come over to you first) and find a way to say “hi” without making him feeling cornered.  You can both probably take it from there.  One important point though: don’t be shocked and, especially, don’t be hurt if he declines your overtures.  We’re used to thinking of men as always interested, but that’s more a function of men traditionally initiating.  If he gets to know you a little better he might change his mind… or even ask you out himself.  Good luck.

Straight Single Guy (Mark): I’m a little past the bar scene as prime turf for pick-ups, but we’re all familiar enough with the scene to know how it goes.  The gender roles are quite different depending on who’s the aggressor, and in this case, it’s a little more straightforward.  First, just approach him and strike up some decent general conversation — truthfully, the odds of this being received well are high, even before any chemistry is determined, and you get points already for being outgoing enough.  Soon enough, if there’s any semblance of a spark, just come right out and be candid about what you’re looking for, whatever that may be (a number for some future potential, or just to go home and get naughty) — more points for the assertiveness.  If he’s into you, then game on!  If he’s not, any reasonable guy will still be flattered enough, and probably offer some polite enough version of “no thanks” (no worse a rejection than if you’d used some other cockamamie strategy).  Either way, cutting to the chase gets you your answer without anyone having to play any crazy games, imagine that.  With picking up guys, it’s pretty simple — just go for it!

Our “guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Gay Guy is one-time stripper and sex columnist Daniel; our Straight Married Guy is Figleaf, the guy behind RealAdultSex.com; and our Straight Single Guy is Mark Luczak, a tech geek at Carnegie Mellon University. To ask the guys your own question, click here.


  1. Hi
    Chrissy, If the guy knows you are married they probably won’t make the first move. They are unsure what you are looking for especially if they are a friend as well. I was like you looking for an affair when I was married but it didn’t happen with the few I was interested in until, unfortunately, I separated. Then out of the blue all three guys have approached me for a relationship. Men are ok to have a relationship with someone else’s wife, but someone a bit removed from their social circle.

  2. I am a married woman for 24 years and am looking to have an affair with other married men. No commitment there, just sex. Since I have been out of the market for so long, I am way out of the loop.
    So far I have a couple men picked out and have the casual conversations with them every time i see them. I do believe they are both interested, but won’t make the next move. They will approach me from across the room, but have never gone further. I would love to peruse them, but I am also afraid. I would really like to hear some advise on making the next move from some men as well as women.
    Just loving all the tips.

  3. Men are always on the watch for women who are open to being approached, talked to, asked out. Women are used to avoiding eye contact or smiling at men because those usually lead to a guy walking over to you. So for a lot of women, just looking at guys and smiling will be enough to get them to talk to you. If you want them to take the next step, touch them on the hand or arm with your finger tips and say “that is so interesting” or “that is so funny” and the next thing you know, he will be trying to get your number, ask you out or take you home.

    If a girl buys me a drink, I just start thinking about sex, because drinks lead to sex!

  4. Daniel said: “Wouldn’t your heart just melt if you met a genuinely straight guy who loved shopping for clothes and talking about it?” LOL!

    No Dan, I’d be suspicious. 😉 (Wow, 5 dates and he hasn’t tried anything yet. What a gentleman. 😉 ) Dated some guys, spent my college years as a….hag, (probably still am, according to some friends) and I have yet to meet a straight guy who really likes to shop for clothes. *sigh* That’s why we have Gay Friends. (Well among other reasons.)

    I’m serious, the last time I tried to get my Man to go clothes shopping with me (for a wedding on HIS side of the family) he continued to stare at the TV and mumbled, “Don’t you have a Gay Friend you can call?” So I did.

    My Man shops for his own clothes with the speed and grim determination of Hercules cleaning the Aegean Stables. RUNS through the store, pulling things off racks, barely glancing at the tags, throwing them over his arm (because he forgot to get a cart, “I only came in for two things.”) and races to the checkout, with his jaw set, in 3 minutes flat…..with only the two things he came in for.

    He prefers if I just pick up “anything” for him while I am out shopping, when I start to find holes in clothing, “Damn, I’ve only had these jeans since my Junior year.” (he’s nearly 50.)

  5. I’ve got to admit, as i’m writing a book, i actually came on here to get some insight into how women flirt and show signs of interest; but the points they make about men are very true. If you want a one nighter, then be a bit more superficial and outgoing; because, you’ll be more likely to have success with people who are looking for the same. However; if you are looking for something more, then use flirtation, etc, as nothing more than a catalyst for striking up a conversation with the right person and showing him a deeper side of yourself…at this point, they’ll give some sort of subconscious clue as to where their interests lie. For instance; a man only looking for sex will act like a dear in the headlights if you throw a surprising act (i.e. offering him a drink) at him. This is because the man has a game plan; and it works because the girls he picks up will normally act in a very mechanical manner; and if you throw an emotional curveball at him, you can identify him immediately.

    Try it 😉

  6. i got 2 say if a women came up 2 me and offered 2 buy me a drink i wouldn’t b intimidated at all actually that would b down right sexy and if she looked good it would def. b on.. so ladies thats probly the best way 2 go about it.. atlest wit me

  7. I’m a straight 19 year old guy and I think that a girl can just be upfront with it all. Just tell us you are interested and ask for us to get you a drink (that could be a sign that you would not rule out drunken sex or you want to chat.) I really like it when girls ask me out, it’s less work specially if you already find the girl attractive (everybody wins)..I think that all modern day guys (guys who are not afraid of a strong independent woman) would love it if we kept getting asked out by women instead of us doing the chasing all the time; because frankly it gets a little exhausting after a while. Or it could just be me, I love women but the whole process of getting them to fall for my lies and stupid game is just a huge hassle. If it was possible to just get them without all the work why would I say no

  8. I think Daniel’s idea is pretty good, because it’s new and unexpected. However, I think straight men are scared of strong independent women. So I’m not sure the whole ‘her buying him a drink thing’ would really work in the real world.

    I love the columns. Keep the good work, guys!

  9. Great advice, wise guys! I think Daniel’s approach is quite refreshing and unconventional. That whole scene he described of a lady coming up and offering to buy a drink…totally hot and sexy.

  10. First, let me say, I love the Wise Guys columns – I only wish it had been around when I was still trying to figure out my huband (thankfully after 16 years, we’ve got it worked out). I have a single friend my age (not a hypothetical friend, I promise) who is very successful and would rather not be single. She has no hesitation asking men out, but her impression is that most guys aren’t comfortable with women being the “aggressor” for anything other than a booty call, particularly in public.

    I’m not sure if it is because men over 40 (our age group) favour more traditional roles, or perhaps it’s just the type of guy she’s attracted to. Any thoughts? Do guys prefer being the one who asks?

  11. I feel like in a relaxed bar scene, if the guy’s really interested, he’ll probably follow up on any subtle flirtation you give. I’m all for asking the guy out, but in this sort of setting, unless the guy is terribly shy (which, in that case he’d probably be scared to even make eye contact with you), he won’t need much coaxing to ask for your number–IF, like I said, he’s really interested. In my opinion, coming on too strong in a bar might indicate you’re only looking for a one-night stand. Which, if you are, go for it! Who cares if you’re rejected then.
    I thinking simply striking up a conversation is always a good way to go. If the guy’s into you, he won’t be too picky about what the conversation topic is 🙂

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