When/how is it appropriate to hit on someone?

So… I’m poly, have a high libido, and enjoy meeting new people. I also am seriously worried about coming across as overbearing, creepy, or douchey, and want to be a good feminist. So maybe you guys can help me out - when is it appropriate to try to strike up a conversation with someone, based primarily on your physical attraction to them, with the intent of potentially asking them out on a date? (To hit on people, in other words.)

In some cases, I’m pretty aware that it’s a bad idea - when they’re at work, for example - but in others I’m not sure. Some examples where I’ve been unsure/hesitant:

  • At the beach while they’re sunbathing (walking up to where they’ve put out their towel)
  • At the nudist beach while they’re sunbathing (seems a lot worse than a normal beach for some reason)
  • At the pool
  • On the train/bus
  • On the train/bus while they’re reading
  • On the train/bus while they’ve got earplugs in (I get the impression this one is generally a bad idea)
  • At the supermarket
  • Randomly walking down the street (seems unlikely to go well)
  • Working out at the gym
  • Hanging out in front of a landmark/fountain/etc.

Situations like that.

Let’s assume that for any given interaction, I have some measure of decorum, act generally respectful, and don’t come off like a total weirdo. I’m assuming the rules are different for men hitting on men, men hitting on women, women hitting on men, and women hitting on women, and while I belong to the former two categories, I’d still be interested in the other two.

And feel free to point out other situations that would/wouldn’t be okay where you think there’s some way people like, say, me could get it wrong. Or just general rules of thumb.

“Why don’t you want to go out with me? It was *appropriate *for me to hit on you. I followed the rules.”

For some reason, I can’t help reading the OP in a mock German accent.

Funerals. Avoid funerals. Especially if it’s your grandma’s funeral. Although I’m sure that even that has worked for someone, once.

Perhaps a little background: until someone explained it to me, I had no idea that it was a really unpleasant experience for a service industry worker to be asked out at work. It just didn’t quite click in my head that this was a really shitty place to rebuff romantic advances, and I’d seen enough of the trope of people leaving phone numbers for starbucks baristas to assume that this was kind of a normal thing. I had, in fact, considered asking out the cute girl working at the local KFC. I know for a fact I wasn’t the only one surprised by this. I’d prefer not to accidentally blunder into other situations like that through stupidity and ignorance, or at least not do so repeatedly.

That said, thanks for your advice, funerals do seem like a terrible idea.

In another thread, I told a (not very interesting) story about my encounter with a lady working at my local pharmacy. I didn’t ask her out. It wasn’t on my mind, and it hadn’t occurred to me before that thread. But we had a fun conversation. We laughed. She was working behind the counter, but she basically *happened *to be working behind the counter. I didn’t hit on her or anything, but I still can’t find it in my heart to think of it as UNPOSSIBLE. At least for certain loose definitions of “hit on”. Even though the thread was full of “NEVER hit on people at work.”

If there’s chemistry, there’s chemistry. Sniff the air for chemistry, I guess. No pharmacy puns intended. If you like the KFC girl, and she already likes you, then why the hell not?

That’s different than harassing the checkout girl at the local supermarket. Or drunkenly hitting on bartenders who get hit on all the freaking time.

Oh, BTW:

Hi! I’m hairy, have a large shoe size, and I’m currently holding a massive aubergine. My favorite movie is “2001: A Space Odyssey”, and my favorite musical artist is Leonard Cohen. I like walks in forested areas, and randomly scaring tourists. Want to go on a date?

Hang on, I have another one.

I had this STD test once. The doctor was a lady. She was young-ish, blonde. Very pretty. She seemed pretty cool, too. I had read up on this particular STD the day before, because I study for my STD tests. (Yes! Finally got that joke in, awkwardly.) She was so impressed with my knowledge that, after she was done taking samples, she let me look through her microscope. The whole thing was good fun.

And I was sort of idly thinking to myself: Would there be any point during this encounter where it would be appropriate to make a romantic advance? Before she’s scraping skin samples off my schlong with a scalpel? While she’s doing it? Or after?

Not that I was going to in a bazillion years, but you know. Hypothetically. I concluded that, no. No, there really wasn’t one.

Besides, she was wearing a rather prominent wedding ring. I was also sort of wondering if there was a reason for that. Besides her being married.

Approaching a stranger unknown, based solely on their looks, seems a little skeevy to me (apologies if skeevy seems too harsh a word).

If all you care about is one’s looks… well, there’s an app for that. And you needn’t bother random people going about their day.

If however, you find yourself striking up conversations with people for reasons other than physical attraction, and if you feel a genuine connection, by all means, ask them out.

That said, I’d be very wary of asking people out who are paid to be nice to you. (Waitstaff, cashiers, etc…)

I’m beginning to realize that I’ve never actually understood how this “asking out” thing works. When I think about it, it has only ever occurred to me that I might want to, I dunno, “hit” on someone, for lack of a better word, *after *some chemistry has been established. Or at least something that might be mistaken for chemistry. Even if it’s online. Even if it’s only an exchange of glances. Something, beyond just looks.

Not saying that I’m better that y’all. I’m not. For one thing, I’m just not. I mean, it’s just a fact. I have documentation. For another thing, when I say “after”, it’s sometimes anywhere from six months to eleven years after. For a third thing, I can be so oblivious and insecure that it might take anything up to and including actual sex before I realize that I have chemistry with someone.

Huh. Something just occurred to me about a relationship I was in once. This was ages and ages ago. I was super young. I talked about it another thread, which is why it comes to mind now. I was talking about how the breakup was so benign and drama-free that I didn’t even noticed that it happened.

But I also just realized that by the time I was thinking “I think I like this person, and maybe it would be cool to have a relationship with her”, we had already kissed. And we’d already had sex. I think it’s safe to assume that, as far as she was concerned, we were already in a relationship.

I guess I kind of missed both the beginning and the end of that relationship.

My ex-boyfriend asked out the 411 operator (back in the day). Apparently the connection (hat har) they had on the phone didn’t translate to real life. But hey, nothing ventured and all that…
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Unless they’re on fire, never bother someone with earbuds in.

I wear earbuds frequently. Sometimes I’m listening to music or a podcast. Sometimes the other end of the cord is just in my empty pocket. Please, take a hint or buy a vowel.

Well, how would you meet someone who looks interesting to you? I guess I could put more focus on online dating, but I’ve found that online dating doesn’t really play to my strengths. How else do you meet people? Perhaps the regular gaming meetups are a good place, but given how male-dominated that space is, I feel super unsure about hitting on people there, despite the fact that people there are among the most likely to share my interests.

This is good advice that I will definitely take seriously.

See, the way it tends to work with me is, I see someone I find attractive, and wonder if there’s any chemistry, or mesh of personalities. So I go and chat them up, and see how things go. Is there a problem with this? Is my approach somehow backwards?

Fine. But when I offer you a paper towel, just take it. I know that you’re reading. I know that you’re wearing headphones. But you have a cold. Your nose is dripping, and you’re going sniff every three seconds. I’m not being nice. I’m not making advances. It’s just driving me completely nuts. And this is a crowded train, so I can’t change seats. Really? Sure? I’ll only poke you thrice.

Wait, that probably wasn’t you. Yes, I tried explaining. She didn’t seem to speak English. I think she was Chinese. Anyway, carry on.

No. That’s logical, I guess. I suppose I hadn’t really thought about it. Yikes, though. How many people do you have chemistry with? Don’t you have to approach boatloads of people to find one? It sounds exhausting. Seems to me that it would make as much sense to go about your day, where you talk to people anyway, wait for the chemistry, and then do the thing. Maybe not, though. What’s your signal-to-noise ratio?

And yes, I know about the “pickup artist” thing. But that’s different, right? As far as I understand it, that’s about getting people into bed, regardless of whether you actually like them or not. Or, well, more or less that.

That’s the problem with kids these days. Unless it’s through an app, most of them have little idea how to actually interact with other humans.
The answer to the OP’s question is that there is no wrong answer, so long as you don’t act like a jerk. Really, the question is “when is it appropriate to strike up a conversation with a total stranger?”. Are they at work? Do they look like they want to be alone? Are you creating a situation where a person is forced to talk to you (like an elevator or subway).

Generally the “problem” with hitting on a total stranger is that people naturally are leery of total strangers who seem like they want something. Also, the whole “pick up artist” thing of guys using canned lines and routines like a salesman pitching potential clients is pretty skeevy as well.

The “how” is basically you pay close attention to their mannerisms and body language and realistically gauge whether they are interested, just being polite or reaching for their mace and rape whistle.

I would say:

  1. Make sure you’re not blocking their exit route. On a train is a bad idea, usually, because if they feel weirded out (probably for reasons that don’t even relate to you) it’s easy for them to feel trapped into being nice. This is also why hitting on people who are working is a problem.

  2. Have a little conversation first before you pop the question. If they’re not willing to chat for a couple minutes, then they probably don’t want to be put on the spot.

  3. If you get rejected, head for your own exit route, with a pleasant smile and maybe even a, “Thanks for the chat!” Move away promptly so that they don’t feel like they have to get away. Take it on yourself to give them space.

If you cross paths in the future, limit your contact to a smile and little nod, before ignoring them. Leave the ball in their court.

That’s how I see it.

Well, fair point. For my part, I guess I mostly don’t, unless I happen to.

Or, I might talk to their dogs. There are lots of people around here with dogs. Usually, I only talk to the dogs, because I’ve grown to enjoy meeting dogs. The ones around here usually like me. Although they also like to sniff my crotch a bit too much. I’m still working on my dog-whispering style, I guess.

Just now, there was this lady outside. Not an, as you put it, interesting looking lady. Just, you know, a lady. She said “hi” to me. I didn’t have a clue who she was. But then I recognized her dogs. I’ve talked to them lots. They come up to me when I’m sitting outside, smoking. Apparently, the lady thinks we’re acquainted now. Sorry, lady, I only know your dogs. Anyway, where was I?

Oh, yeah. There was an interesting looking lady around here for a while, too. Quirky dress sense. Good looking. So, I tried talking to her dog.

But this one barked at me, and growled. I guess it had instincts. It could sense that I was going for the owner. Or it was just an asshole dog. So, well, I’m not sure. I guess you meet more people than me.

*Nice weather we’ve been having.
*
Yeah.

How about them Yankees?

Yeah.

Will you marry me?

Except in romcom movies, not a good idea to approach strangers in a public place and ask them on a date. That is just creepy. I would nix all but one of the situations you list in the OP. That person has no idea of whether you are a nice person that something could work out with, or a total psychopath. It is more acceptable if you meet people in social situations (parties, going out with a group of friends), other situations that are not social in nature but where you get to see the same people repeatedly and can have more than one conversation with them (classes, gym, but work is not ideal), or other situations where the person you are interested in will feel safe. I once asked out someone I sat next to on an airplane, but that was after an hour and a half of conversation.

I’m not sure the rules must be followed at all times. The ‘‘getting hit on at the beach’’ concept sounds creepy to me, but there has to be an exception, some confident woman somewhere making eyes at the guy playing beach volleyball… I dunno, I’m not sure how attractive people work. Do they play beach volleyball?

To me it’s all about context and body language. Pay attention to nonverbal cues. If she’s got her nose buried in a book, that’s a good nonverbal cue she wants to be left the fuck alone. If she’s got her nose buried a book but keeps looking up at you and smiling, maybe that’s a game-changer.

I trust someone like you to use their best judgment about what is and is not appropriate given the circumstance, to pay careful attention to the body language and signals you’re getting, and behave accordingly.

Often when we say ‘‘Do not do this under any circumstances ever’’ we’re talking about the idiots who don’t grasp the basics of nonverbal (or even verbal) consent. There are a much higher percentage of those out there than there are of you. I would say it’s not wise to approach a woman who isn’t giving you some indication of interest. Believe me, if she notices you, she’ll make sure you know it.

This thread is even more enjoyable if you imagine the OP using this as his pickup line. :stuck_out_tongue: