Dating question: When is it ok for a man to approach a women he doesn’t know to ask for her number?

In My Humble Opinion
1

So, my divorce was granted last 9/11 (so apropos); we’d been separated for 2 years prior to that. Me, an introverted man who works a lot, did date 2 people during that time, but one came from a dating app and another was, well, an unsustainable one-off (for reasons).

I’m fine with single-hood, but occasionally you get that itch, and another round of online dating app yielded little but a quasi-stalker (harmless though she is), and online dating advice was that you shouldn’t be relying on online dating anyway.

The advice, from female dating coaches, was instead a reassurance that women want eligible men to approach them and speak with them.

So…just approach.

What confounds me is that this necessitates a little dance, wherein you must first banter, to achieve the end of approaching a woman to ask for a date.

And so, in the thread about normalizing things, I offered

To which I got the following (friendly; I’m not at all bothered by these, as I think they make for an interesting discussion) replies

Now, let me clarify a few things. One, as I noted, there are reasons why this may (and oftentimes is) not appropriate. Some women are busy and not to be bothered; some are with people, who may or may not be their significant other. And I also get that people feel far more comfortable getting to know somebody if they’ve at least talked with them first, so an immediate request for a date is off-putting.

I personally hold to a theory that a woman makes the first “move” in any “just approach” interaction- it’s likely subtle, but it would be something like a smile, or positioning herself in a position to be seen and confronted while making eye contact.

Secondly, I realize I’m over analyzing what is simple human interaction. I’m doing so here because we are the Dope, and it’s something I find curious about human behavior. So if it comes across as creepy, I do apologize in advance.

I fully understand that women are not merely conquests, and that male female interactions are not “moves” to obtain sex. I’m not an Incel or anything, but the courtship of humans is compelling, especially as a person who has to make a conscious effort to put myself out there.

Finally, this isn’t my request for dating advice. I actually managed the courage to get the phone number of the mom I’ve been speaking to at my son’s martial arts practices. Instead, I’m really just interested in this:

2

This would be good. I don’t care if folk think its out dated, but if a man doesn’t pursue a woman he isn’t interested. I have made the first move way too many times, and the guy figures, oh well, might as well take her for a bit.
Being too bold is bad, but a conversation about anything like the weather.

3

For me , at least , it’s got nothing to do with personal space or privacy. If it did, I’d get annoyed when a man started to talk to me about the weather or how expensive the apples are. My issue is that if a man just walks up to me and proposes a date , there are only two things I know about him. He’s willing to commit to a date based on nothing other than how I look, which already makes me inclined to say no. Apparently looks are important enough to this person that he doesn’t even feel the need to talk to me for a few minutes first to see if I’m such a wack job it’s immediately obvious. The second is that business about too awkward to make small talk but not too awkward to ask me out. It seems weird to me and I’d be worried that the weirdness wouldn’t end there.

4

Yeah, this. IMO, the only way to skip the small-talk stage AND make it not weird is if you’re in a venue where it’s already assumed people are looking to meet someone, like a singles event or a bar / club that is a known hookup spot. But even there, why would you not want to find out first whether they’re someone you actually like?

5

Everything @doreen said, plus: why on earth would a man think I’d want to date someone I know absolutely nothing about? I don’t think the OP is conceited - far from it - but the idea of a man assuming I might want to go out with him despite the fact I know nothing about him is kind of gross. Seems like he’s either assuming he’s incredibly attractive, or I am desperate.

6

What if he just asks for a phone number? (The difference being that you’d communicate by phone before discussing whether you’d want to go out on a date)

Yeah, in the other thread I phrased that poorly. I guess what I was lamenting was the fact that the whole social interaction is expected to begin with some banal discussion about something, when the reason for the discussion is to obtain a way of communicating for the prospect of a date.

So, yes, while it’s normal and expected to go some version of “what brings you here”, with the hope of being witty and getting a positive vibe, it’s, well, cumbersome.

Undoubtedly it has a purpose; it, in theory, provides a polite way for the woman to reject the advance, and it also offers her a chance to assess whether she even wants the advance at all.

I guess I just don’t like small talk.

7

That’s kind of a risky theory.

It reminds me of an antivax celebrity (on X) med student who was convinced that nurses he encountered were coming on to him.* He was recently bounced out of his program for what may have been related reasons.

*“Yeah I love the nurses and love to compliment them. I think I might be in some small trouble for flirting this coming week. I had no idea I had to watch every single word that comes out of my mouth.”

8

Isn’t the whole point of going out with somebody to find out about them to determine if you like them and want to spend more time with them?

Would it change the equation if the reason they came up to you was because they saw something about you that led them to think that they may have something in common with you? what if you were reading a book and they came up to you and said “I’ve read that book. I’d love a chance to talk with you about it over coffee sometime. Here’s my phone number.“

Would that be considered gross?

9

Miss Manners once said this kind of thing is proper if both of you met ‘under the roof’. Of a church, school, class, a club, the office - where you probably have something in common - and something to talk about if you approach a stranger.

I would run like the wind if some stranger approached me in public, out of nowhere, coming on to me and asking my phone number. I know it’s against every Hallmark Movie meet-cute, and I know it happens and people hook up and live happily ever after (with a nice how-we-met story). And it’s not that far removed from meeting up from an online dating app. I may be prejudiced, I’ve been followed and almost grabbed by handsy strange men a couple of times, simply walking through downtown heading for the bus stop.

Yes, it’s tiresome and dreary to try to make small talk instead of cutting to the chase, but one must suffer through it. (Easier to drop one’s pants and point without words, I know.) At least opening your mouth to look at each other face-to-face and say a few words about the quality of the deli salad or where to find the party goods in this huge store is a start.

10

There are two times I gave my number almost immediately to guys who came up to me out of seemingly nowhere, and started a conversation, and then ended up dating them. Neither of them proposed what was necessarily a date, though it was further interaction. And, we skipped “weather” talk and went to something in the middle area of talk-- not intimate, but practicably personal.

One came up to me when I was about 22 and said he understood from mutual acquaintances that I played D&D, and he was getting a game together, and was I looking for a game?

The other time, we were the only two teenagers at a showing of a silent movie not there with our parents (or grandparents), and he asked if I went to a lot of old films, or if this one was special. We ended up going to a lot of old movies together, since, in fact, most of our friends weren’t interested unless it was something big, like Gone with the Wind, or sci fi, and not all that old, like The Day the Earth Stood Still (I was a teen in the 80s).

One time when a guy came up to me and tried to pick me up out of nowhere, he was unsuitably old for me, but I was at a university library, wearing a sweatshirt for that university, tall, and somewhat developed for my age, so I never knew whether he was being creepy, or made an honest mistake.

So, really, you ought to do a sliver of info gathering on a woman before approaching her.

If she’s 10 years older or younger than she looks, still mourning a miscarriage, or just won the lottery, those are important things to know.

11

The part about the book makes all the difference in the world.

12

As I figured it might.

But, if having a mutual reading interest is relevant, then why isn’t mutual attraction? Now, I get that the woman may not be mutually attracted to the guy, but he’s going up to her to find out if she is. So, let’s assume that is so. Is there anything wrong with people deciding “I think you are attractive. You think I’m attractive. Let’s get to know each other to find out if we have other things in common that make us compatible.”

I’m guessing that mutual attraction is too superficial a quality, but I also believe that this is the reason that a lot of relationships begin.

13

That’s worse. Why on earth would I give my phone number to somebody I know nothing about, for a reason I know nothing about? I get enough junk phone calls as it is.

Even if you’ve had some conversation: for men, don’t ask for a woman’s number. Offer her your number instead. If she wants to talk, she’ll call. If she offers hers in exchange, then you can call her. But she may want to think about it – and one of the things she probably wants to think about is whether you’re going to push her for information she may not be ready to give.

You’re lamenting the idea that you ought to talk with the person first, in order to get some idea whether you even want to ask them for a date? and to give them some idea of whether they want to have any further interaction with you?

AIUI, even on dating sites on which the whole idea is to find dates, it’s usual to have some conversation before agreeing to meet.

That’s better – except, wait till she looks up from the book, and see what she does when she notices you. Interrupting somebody who’s really into a book isn’t polite. And – she may be reading the book casually while looking around at people at intervals; or she may be reading the book seriously and/or as urgent work; or she may be using the book as a defense against being spoken to by random people.

The problem is that for some people the only thing they’re interested in sharing with the other person is sex. If that’s true for both of them, no problem – but it isn’t true for a lot of others. Expressing (preferably genuine) interest in something else about them is a way of expressing that you’re not only looking to get laid with Something Female, you’re interested in an actual relationship with Specific Person.

If you are only looking to get laid and don’t care about finding some Specific Person who you want to hang out with otherwise, then go to a singles bar or something of the sort. Not that everyone at a singles bar only cares about the sex; but that it’s more acceptable there and your chances of finding somebody else who just wants to get laid are higher.

14

This is all hypothetical, mind you, but the reason would be that you are not dating somebody, would be open to dating somebody, and you’ve been approached by somebody that - if they were nice and decent and smart and employed and not a creep and whatever other standards you’ve set - you would like to date.

The reason is that they are not dating somebody, would be open to dating somebody, and they think - if you were nice and decent and smart and employed and not a creep and whatever other standards they’ve set - they would like to date you.

I’m not trying to be flippant. The pretext of somebody trying to start a conversation with a stranger while out in the world is usually related to an interest in getting to know them better, and that interest is usually triggered by some measure of physical attraction.

I don’t see anything off putting about that.

(And the reason I emphasize the hypothetical part is because you personally may be married, or not interested in dating, or have some reason to decline any inquiry. But, generally, I don’t see anything gross about it).

I’m distinguishing between the sort of “getting to know you” conversation that’s a part of newly dating somebody and the type of discussion that is part of asking if you can go on a date. One is interesting and fun. The other is odd, to me - if I see somebody I’d like to know, I must find something, anything to talk about other than the purpose of the conversation. I mean, other than deciding if I stutter or have bad breath (or can make a joke), that initial banter doesn’t exactly convey anything about me.

Of course not, and I do personally err on the side of polite. In my OP, in fact, I mentioned how I personally believe that it would be foolish to try to make conversation with a stranger who didn’t at least make eye contact and smile.

But my point in mentioning the book is that it is a superficial thing that appears to connect the two people, who otherwise know nothing about each other. And, so, if that is an ok pretext to begin a conversation, then some other superficial quality might also suffice.

Yeah, but that can be true of the guy who begins by discussing the book, too.

I mean, sure, if the guy is overtly sexual, that’s obviously distasteful (she don’t even know him!). Or if he never tries to get to know anything else about the woman (he just stopped at “she’s pretty”).

But why is it wrong for a man to merely decide that a woman matches physically, and therefore the man would like to meet her and learn more? Why should he lie, or prevaricate, about the feeling? If he is otherwise respectful, why is it bad that his physical attraction has motivated his interest?

15

They may be all that, but there is no way to know this from some guy just walking up to a woman and asking for her phone number.

16

Isn’t that why they exchange phone numbers? To talk more and find that out? And, if it’s going well, meet up again?

Do all of you people require your dating prospects be vetted by somebody else first? It can never begin with a chance meeting?

17

I’m a guy, and while it’s been a while since I dated, I never simply asked a woman out (or asked for her phone number) without already actually knowing her at least a little bit (e.g., from having classes together, from other social activities, having been introduced by a mutual friend).

IMO, and take that for what it’s worth, but walking up to a person about whom you know nothing, other than you find them physically attractive, and asking to go out with them (which is what you’re asking when you are asking for their phone number) is creepy and presumptuous.

You may not be internalizing this, but wanting “to talk and find that out” is asking for a date.

As was said upthread, the “meet cute” chance meeting is a trope of fiction, but don’t be at all surprised when the vast majority of women will be turned off by this, and will be concerned that you are a creep or a potential stalker or assaulter.

18

That wouldn’t be gross and in fact it happened to me once. I was reading Mrs. Dalloway in a cafe and a guy at a nearby table said, “Oh, I love that book!” and started chatting with me about it. It was pretty obvious he was hitting on me, which was fine - obviously we had something in common, which was a love of literature.

As it happened I was in a relationship so I didn’t end up going out with him. But I almost certainly would have otherwise.

19

IMO you should just approach in your best non-creepy way and ask for the number. If rejected, break contact immediately (but politely) and don’t approach that person again.

Will some women find it creepy? Of course. Women aren’t a monolith. What one woman finds courageous or romantic, another may find desparate or creepy. It’s a numbers game, you accept the possibility that your approach may not be received well. But it’s true what others said, some commonality (even minimal) is ideal if you can swing it.

As long as you are nonthreatening and respectful in the face of rejection or disinterest, go ahead and make some practice runs and figure out your best move. The only person whose opinion matters is the person you’re approaching.

20

I used to chat on the Internet with a guy who picked up a lot of one-night-stands, and he said his opening line was, “Hi, I’m Matt”. (That was his first name.) He was very good looking. Most women shied away. But he did it often enough and enough women returned his interest that he claimed to have picked up a lot of women, and I’m inclined to believe him.

(In addition to being a professional personal trainer and having the body that suggests, he was also very wealthy. I’m sure that helped, too. And people i know who met him said he was charismatic.)

So, sure, that method can work. Although i think he did chat women up for a bit before actually asking them out. And i think he also went after women who had looked at him, first. He claimed you can tell within seconds whether someone is attracted to you, and that also seems plausible.

Anyway, “hi, I’m Firstname” is a good opening line. It expresses interest without asking for anything. It’s respectful and nonthreatening. It invites, but does not demand, a similar reply.

(And yes, it will annoy the attractive woman who gets too much interest from men. But at least it will be a brief annoyance, and she can turn away from you and go on with her business. If you try this, expect a lot of women to literally turn their back on you and then try to avoid you. Please let them do so.)