Ways to Approach a Woman Out in Public That Work?

[PassionatelyCurious]

I've always been horrible at approaching women, and when I say "horrible", I mean I get nervous thinking about it, and then never actually follow through. 

I've been told oftentimes I'm an attractive guy for my age (mid 40s), educated, very high IQ, in good shape (workout regularly), and so I've dated lots of women in the past, been married, multiple long-term relationships, etc. But, I almost always met the women through somewhere online, with a select few through mutual friends.

My typical method in the past has been dating apps and websites, but the ratio on those are so horribly skewed, and there are so many flakes (at least on the free ones that I'm assuming aren't taking it seriously, and as you get older, it seems they get worse and worse), that it's EXTREMELY discouraging, and so I want to try something different.

So, one of my questions is when it comes to a man approaching you out in public, say at a grocery store, the gym, poolside at a community pool, just really anywhere in general, what are you women receptive to? If you men have a modest amount of experience getting women's numbers this way, what types of approach works for you? I really don't know what to say most the time, because really at that point, you don't have much of anything to work with beyond "I find you attractive, and while I don't have anything else yet to work with beyond that, I want to see if there could be more by getting your number and getting to know you better", but I don't know if being that blunt would be a good approach?

I know another thing that could help me is building up a social circle in the area, but with me going back to school to further my education, and it being a very study-heavy major (physics), my time is very limited. Plus, it's hard for me to find social groups locally I'm interested in. I've looked on Meetup, but most the groups I'm interested in aren't local groups, and the ones that are local are either about things I'm not particularly interested in, or extremely small. Like the handful of ones I'm interested in locally tend to have 3-6 "attendees" on their lists when it's close to the event. And many of my interest groups are predominantly men (eg. gaming, sciences, astronomy), so that doesn't help either.

Anyway, I'd greatly appreciate any suggestions any of you could give me.

[Gebidozo]

I’m almost 50. I’ve had several long-term relationships, including marriages, as well of my share of fleeting romances and casual stuff.

I never approached unknown women in grocery stores or comparable locations. I imagine that gyms or pools are a better environment for that, because there they are united by a common activity. I never went to either, though, so I wouldn’t really know.

I did approach unknown women in bars a few times, but very little came out of that, at most a couple of one-night stands.

I also never dated online. 

All my romantic relationships, serious or casual, were with women I met in real life, through my studies and work. The majority of them were of  the same profession as I, schoolmates or colleagues, in several cases ex-students.

I think that hitting on strangers in a grocery store is akin to shooting from half court in a basketball game. Sure, if the ball goes in it’s 3 points, but the chances are very low, and doing that on a regular basis instead of creating reliable shots would greatly embarrass the player in question, disqualifying them from any team.

I might be wrong about that, though. Back in college, there was a guy who routinely hit on women in the subway. He approached them and asked, “Excuse me, would you like to have sex with me?”. We pointed out to him that most women would say “no” to that. He said, “Yes, most say no, but about 1 out of a 100 agrees. I don’t care about the percentage, just the result.”

Edited May 19 by Gebidozo

[basil67]

I would say that women are more receptive to being approached when they are in a social situation and expect to be talking with different people.   Like if she gets in a conversation with a guy who's also queuing for drinks at a bar, they find they have good conversation and so he asks her out.   Or if they meet at a party, get talking, find connection and he asks her out.

Do you see the difference here from what you're proposing?  She feels she's being asked out because they have built a rapport and has confidence that a date may be successful.   On the other hand, asking out a complete stranger at the supermarket based on nothing more than the fact she's attractive is not going to go down well.   I have never accepted a cold approach.   But I met my husband at a party

 

[basil67]

6 hours ago, Gebidozo said:

I might be wrong about that, though. Back in college, there was a guy who routinely hit on women in the subway. He approached them and asked, “Excuse me, would you like to have sex with me?”. We pointed out to him that most women would say “no” to that. He said, “Yes, most say no, but about 1 out of a 100 agrees. I don’t care about the percentage, just the result.”

OMG I get the creeps just hearing this story!  

[BaileyB]

As basil said, I think you have to prepare yourself for the fact that the success rate with this type of approach is likely to be low.

I would say - start with a hello. And then, find something to talked about - “that’s a good book, I’ve never read it but I want to!” Or “this line is taking forever today.” If she responds favourably to your attempt to communicate, you can see where that takes you.

[Gebidozo]

4 hours ago, basil67 said:

OMG I get the creeps just hearing this story!  

Totally, even we were creeped out by that, and we were horny college boys with very shaky ideas about right and wrong back then.

 

[Els]

18 hours ago, PassionatelyCurious said:

So, one of my questions is when it comes to a man approaching you out in public, say at a grocery store, the gym, poolside at a community pool, just really anywhere in general, what are you women receptive to?

None of the above, if by "approaching" you mean "asking out". It's fine if you just mean making casual conversation that doesn't have a specific end goal, but it's generally really obvious if the person talking to us has an ulterior motive.

Look, people go to the grocery shop to buy groceries, they go to the gym to exercise, so on and so forth. You don't know if they're married, in a relationship, gay, just not looking for anything, in a rush, are going through a bad spot right now, etc. I'd say your odds of success are probably 1:1000, and your odds of annoying someone are 900:1000 (the disparity is intentional - not everyone who isn't interested will be annoyed at being asked out in such a setting, but many will be).

You're not going to like this answer, but if you want to meet women IRL you have to go to places where people are intentionally going to socialize. And you're likely going to have to get to know those women as people before you ask them out.

As to the type of places that can work... People can and do find success in meeting women at bars, clubs, etc, but considering what you've said about yourself, I think that wouldn't be your kind of scene. And as for the interests you mention, there are women in all of them, but as you said, the ratio of men to women is pretty high in those fields. So you will have to consider making the time and expanding your interests to include hobbies and clubs that aren't predominantly male.

If you really don't have the time to do that, then how are you going to find the time to date, if a woman did miraculously accept your grocery store invite?

Edited May 19 by Els

[Sanch62]

18 hours ago, PassionatelyCurious said:

My typical method in the past has been dating apps and websites, but the ratio on those are so horribly skewed, and there are so many flakes (at least on the free ones ... so I want to try something different.

You get what you pay for. People who are invested enough in finding a quality person will pay for a better site. 

Quote

... "I find you attractive, and while I don't have anything else yet to work with beyond that, I want to see if there could be more by getting your number and getting to know you better", but I don't know if being that blunt would be a good approach?

No, using a woman's looks as an approach will creep her out and give you a rep with the store. Tossing out a little comment to make fun of yourself for a lack of shopping ability or something is benign enough. That allows a person to smile and nod as they move forward, or it gives them the option to volley a comment back.

I'd leave discussing looks out of it--it's patronizing, old school, and not cool.

[basil67]

Another thing to consider: why would a random woman want to date you when she knows nothing about you?   

[Esteban]

22 hours ago, Gebidozo said:

Back in college, there was a guy who routinely hit on women in the subway. He approached them and asked, “Excuse me, would you like to have sex with me?”. We pointed out to him that most women would say “no” to that. He said, “Yes, most say no, but about 1 out of a 100 agrees. I don’t care about the percentage, just the result.”

I'm not sure what to make of this. Did he say that he did that and maybe in practice just tried it a few times and gave up? Or did he literally ask hundreds of women and have sex with a few of them. I suspect it was more the former, unless you can clearly remember otherwise?

[Gebidozo]

21 minutes ago, Esteban said:

I'm not sure what to make of this. Did he say that he did that and maybe in practice just tried it a few times and gave up? Or did he literally ask hundreds of women and have sex with a few of them. I suspect it was more the former, unless you can clearly remember otherwise?

I really have no idea, maybe he was even lying or that was his idea of bragging. The bottom line is that after that conversation we (the other college boys) realized that, while technically it was possible to have much more “success” with women than we did back then, that “success” came at the price of embarrassing and humiliating oneself, as well as causing distress to the 99% of women that would find such a suggestion creepy, disturbing, and offensive.

My partner is very far from being puritanical, yet she told me that every time men approached her like that (on the street, in a store, in the subway, etc.), she just wanted to run away. She says that kind of behavior is always off-putting, no matter what the man looks like and how he talks. 

 

[Esteban]

23 hours ago, PassionatelyCurious said:

So, one of my questions is when it comes to a man approaching you out in public, say at a grocery store, the gym, poolside at a community pool, just really anywhere in general, what are you women receptive to? If you men have a modest amount of experience getting women's numbers this way, what types of approach works for you? I really don't know what to say most the time, because really at that point, you don't have much of anything to work with beyond "I find you attractive, and while I don't have anything else yet to work with beyond that, I want to see if there could be more by getting your number and getting to know you better", but I don't know if being that blunt would be a good approach?

 

I am 45, M and not speaking from much experience on this type of tactic specifically but more general life experience. I hope at least one woman can reply to my post and comment on what they agree with and don't.

What you describe above sounds like a terrible idea, as it will be slightly distressing to many women and usually won't work.

The key here is that (after evaluating that you are somewhere where a woman would feel secure and glancing all around for possible husband/boyfriend detection), and after saying hello or excuse me to make sure you have their attention, the first thing you say, in a public place, should not be a chat up line, or saying that she's attractive. Partly as that won't work, partly as that would be distressing to many women, and also to make it less nerve wracking for you, and also to minimize the risk of awkwardness if she gets annoyed with you for chatting her up in a public place or if her father/brother/boyfriend will suddenly appear. For the first 2-3 minutes you need to have plausible deniability (i.e. you could plausibly claim you weren't chatting her up incase things get awkward) the conversation should be entirely neutral, not even flirty. Granted, there is the risk of missing out because they don't even realize you were chatting them up but that's a worthy trade off.

Still needs a little boldness though. Start by saying something observational, at the grocery store you could say "do you have to weigh this first somewhere or just take it to the check out" "do you know how to cook this?" or "I'm never sure what to pick, so many options" if you're parking your car you could say "do you have to pay to park here" or "do you know if I'm Ok to park here" at the bus stop you can say "can you get a bus to x from here" or "do you know if they still accept cash on buses" etc. Even a slightly dumb question is not too bad, as long as it's not really dumb or has a really obvious answer. Now the majority of the time you will get a neutral response or a negative response. If they say "don't know, sorry" in a neutral voice and look away sorry it's conversation over, leave them alone.

Just try to feel out whether they really want to be in a conversation with you. If they are speaking in a positive tone of voice, or smile, or make eye contact, then, after maybe 2 or 10 minutes gently flirting with a smile or hold the eye contact for a beat more than normal, for example. In the first 2-3 minutes, it's actually better I think if she doesn't realize you're chatting her up. By 10 minutes, if she's actually engaged in the conversation, it's fine if she realizes/suspects, as long as it isn't explicit. If you're unsure, just wait to see if she says anything, move one step away and see if she moves towards you or looks at you or says something etc.

Don't get her number too soon! Rookie mistake. You walk off after 15 minutes with her number all pleased with herself but maybe she gave you a fake number or plans to block you later or later she starts to have doubts. She won't want to agree to a date with someone she only spoke to for 15 minutes. You thought you won, but you blew it. Women often need to make a connection and have a good conversation before they are interested. You need to keep the conversation going for as long as possible and ideally move it into a spontaneous drink. 1-2 hours is ideal. Only ask for her number after 15 minutes if she has to leave, since nothing to lose at this point. Only end the conversation if you have to, keep it going even if you've got her number as well. Getting the number doesn't have to end the conversation.

Don't bottle it though, if you think "hey it would be nice if I bump her to again in this same place when I'm here next week" sorry but you probably won't and you've just bottled it.

Move it from neutral to slightly flirty but keep it conversational and try and find a few points in common and try and get some laughter going if you can (not essential).

Now after you're lying in bed with her a week/month later having already have sex you can actually tell her "I actually saw you from across the street and thought you were hot, so I ran across the street to speak to you" and she will probably laugh and might not care that it wasn't truly spontaneous, and perhaps she knew right from the first second exactly what was going on. But if you actually walk up to someone and say "I just crossed the street to speak to you because you're beautiful" they might feel a need to run away or call the police. Just how it is.

Most women don't like the idea of someone hitting on them in public with a line, but they do like the idea of a spontaneous meet cute, in fact many women are sick of Tinder and would love it to happen. After all the romantic movies are full of such things, often the first meeting in a romantic movies goes like I described above. You need to make your chat up seem more like a spontaneous meet cute than a chat up. She needs to feel secure and under no pressure, especially at the beginning. If you sense she seems pressured, find a way to give her an opt out.

Edited May 20 by Esteban

[Els]

18 hours ago, Esteban said:

I hope at least one woman can reply to my post and comment on what they agree with and don't.

I mean, it's a LOT better than what the OP is planning to do... So that's something, at least?

I still don't see the point, though. Why go through all that instead of joining a mixed gender hobby club or something like that? It's one thing to have tried those and failed, but the OP hasn't even tried to join anything that isn't male dominated. Because he apparently "doesn't have the time", but somehow he'd have the time to constantly chat up women buying groceries and hope that one bites?

When you're meeting women organically though hobbies, clubs, parties, whatever... You're doing a few other things at the same time, namely making friends and having fun. And you'll learn social skills, which frankly I think the OP could definitely do with.

When you opt for the "spray and pray" tactic... Well firstly you're not even really "spraying" because you're putting in so much time to move a conversation forward with a woman that you know nothing about. But secondly you don't learn or gain anything else from it. It's objectively a complete waste of time unless you get a bite, and the odds of that happening are low.

[basil67]

On 5/20/2025 at 12:47 PM, Esteban said:

first thing you say, in a public place, should not be a chat up line, or saying that she's attractive. Partly as that won't work, partly as that would be distressing to many women,

You asked for feedback from women....

Speaking for myself only, being hit on in public isn't distressing, it's annoying.  And the prettier she is, the more it will happen and the more annoyed she gets.   And striking up conversations over vegetables is very transparent

I'll stick with my response above, that being approached in a social situation is preferable.   With the caveat that he doesn't join a hobby group with the GOAL of meeting a woman

[Lotsgoingon]

You don't want to "approach women" in a store or wherever. Instead, you just want to say "hi" to someone you want to say "hi" to. Just making eye contact enough to say "hi" is huge. 

 

 

 

 

Edited May 21 by Lotsgoingon

[Sanch62]

1 hour ago, Lotsgoingon said:

You don't want to "approach women" in a store or wherever. Instead, you just want to say "hi" to someone you want to say "hi" to. Just making eye contact enough to say "hi" is huge. 

I agree that 'approaching' a woman at random will prompt her to guard herself against you rather than be receptive to you. Approaching signals that you're taking a survey or asking for money or handing out a flyer. She'll be immediately turned off.

I've had people toss me a funny comment in public that will cause me to laugh or volley back a comment. Sometimes this opens a mutual conversation. But anyone who might 'approach' me would cause me to step back and find a way to get away. Don't do it.