With more and more women speaking openly about street harassment, a straight man can get a little confused about approaching a lady in public. "You mean a woman doesn't like it when I pull off her headphones on the subway?" he might say. "What if I stand too close? She doesn't like that either? It's like you can't even talk to anyone without being labeled as sex predator anymore! Damn feminism!"
If this is you, then yes. You're an idiot and you probably shouldn't talk to anyone. Ever again. But let's say that you're just a chill dude who still can't quite grasp the best way to approach an unfamiliar woman in a public space. Your confusion is okay. Dating and flirting is, in general, an awkward thing to do and that goes double for when you're going up and introducing yourself to someone out of nowhere. But guess what? It is possible to approach a lady in a respectful and flattering way that probably won't leave her feeling offended or worried that you might be a subway masturbator.
When the right approach isn't obvious, it's not always easy to discern what's okay and what's not. In the interest of human connection, here's a handy guide on how to approach a woman in various situations.
On the Street
Let's start with the toughest one. Say you see a girl on the street who looks exactly like Amy Pond from Doctor Who or is wearing the t-shirt of your favorite obscure '80s hardcore band. You want to say hello, understandably, but first, please take notice of whether or not she wants to say hello to you or anyone else for that matter. You may think it impossible to make that call, but women are human beings and, just like other human beings, they show signs of wanting to be left alone. Is she walking fast? Is she not making eye contact with anyone? Is she focused on the sidewalk or her phone? If the answer is yes, then maybe you should let it go; she probably doesn't want to be bothered and you have to respect that. Remember, no one other than your therapist or attorney owes you a conversation — so be fucking cool already.
What if she's not power-walking in the opposite direction or actively avoiding looking at anyone on the street? Then it might be okay to approach (remember, different people react to things differently). The most important thing, as is the case when talking to anyone, is to treat her like a person (\ˈpər-sən\). Don't make kissy noises at her like she's a dog (we women tend to really hate this), don't imitate the sound you think her butt makes when she walks (a "hello" is much more effective than "badoombadoombadoom") and don't tell her that she'd be prettier if she smiled. She knows what face she's making and doesn't want anyone telling her to change it.
Granted, approaching someone on the street is tricky. Chances are that you'll be shot down, so be prepared for that. You interrupted someone's day, plain and simple, if they respond negatively, the only thing you can do is sincerely apologize for bothering them (and do so quickly; don't get dramatic or make a thing of it) and politely get out of her way as quickly as possible.
Also, is it dark outside? If so, leave her be.
At a Cafe
Again, take notice of what she's up to. Is she studying? Is she speedily typing on her computer? If so, she's a lady with an agenda and, by interrupting her, you risk being a jerk. If you aren't deterred by that, then the most important thing is that you don't make her feel embarrassed or like she has to leave. Try to pick a table that isn't directly in her line of vision; this way she doesn't have to stare you down on the chance that she rejects you. Try approaching her as you're on your way out the door, apologize for interrupting her (really, most people don't mind being bothered if you politely acknowledge the possibility that you might be bothering them) and make your case with kindness and confidence. If she says yes, great! Months from now, you might be arguing over seating arrangements for your indie wedding or mounting a sex swing in your newly shared home. If she says no, nicely respond with an "Okay, cool. Just thought I'd ask," and then get out of her way.
If you both happen to be regulars, all the better. Start saying hi, warm up to "how are you?" and establish a rapport. That way, when you ask her out, she'll be far more likely to think of you as the nice guy from the coffee shop instead of the creeper who keeps trying to interrupt her as she reads A Visit from the Goon Squad. Of course, she might still say no and unless she's been explicitly telling you how much she wants to go out with you and giving you bathroom handjobs throughout the course of your conversations, you've got to let it go. And remember: She's not a bitch. She's just not interested.
On Public Transit
Keep in mind that women deal with sexual harassment on public transit all of the time. When we get on the train or bus, the majority of us are pretty guarded and with good reason; we've most likely dealt with some shit. We're not being paranoid or defensive when we don't want to talk to you. We're remembering the time just yesterday when someone literally rubbed their naked dick on us (Mondays!). It's easy for you to get defensive and say, "Well, I would never do that," but try to remember that the majority of us aren't fucking psychics and we have no idea what you'd do or not. My point is that if you're going to hit on girls in the subway, expect to be shut down. For one thing, the majority of us don't really like to be asked out in closed space that's often used as a toilet. Secondly, I once had a man on the Q train refuse to break eye contact with me as he ate an entire rotisserie chicken with his mittens on. Public transit is not a safe space.
But maybe you see the woman of your dreams and want to proceed anyway. If you catch her eye, politely smile at her. Does she smile — and not a perfunctory tight lipped one — back at you? Does she keep making open, non-suspicious eye contact with you, too? As I've said before, women are people. If we like what we see, we send signals of our own (generally hard winks and and excessive lip-licking, but we've been known to be more coy about it).
So you decide to go up and talk to her. Try complimenting her on something that isn't physical or sexual. It's easier than you think: "Awesome sneakers." Or, "Is that a vintage messenger bag? I want one, but I'm worried the straps will hurt my shoulders." (If she lets you try it on, consider running away with it. Just because you're not a pervert does not mean that you can't be a mugger.) If she seems open to conversation, chat away, staying friendly and light. If she doesn't, smile politely — again, POLITELY — and leave her alone. Half of the worries women have on the subway is that someone is going to go off on us for being bitchy and entitled just because we don't want to be bothered. Don't be that someone.
Oh, and please don't approach us if we're reading or listening to music. Those are things we do to be left alone. Half the time, the headphones we're wearing aren't even connected to anything.
She's Your Server in a Restaurant
I worked as a server in a restaurant for many years and watched my colleagues get asked out in several different ways, with some methods being much more successful than others. If you're a bro at P.F. Chang's who thinks he's really hitting it off with his waitress, stop and remember that your server might not be as into you as you are into her. While she probably is a lovely person in real life, a huge portion of her (or any server's) income is based on her ability to make you and the rest of the table like her. By being nice to you and making you feel welcome, she is doing her job.
But maybe you think the sparks are there anyway. Maybe she did that whole hard wink, lip-licking thing that I mentioned earlier (seriously, women do this all the time). If that's the case and you want to ask her out, go for it, but do it after the bill is paid and she has already been tipped. It's shitty to make a woman feel — even if you're doing it unintentionally — like her income will be determined based on whether or not she says yes to going on a date with you. By settling your tab beforehand, you give her the chance to respond with honesty. If she says no, don't take it personally. As is always the case with strangers, you don't know anything about her life. She could have a boyfriend, she could be gay, she could be just plain disinterested. So chin up, act respectful and carry on.
If You Sit Next to Her On a Plane
Nope. Leave her alone. Unless we're on Rihanna's 777 plane or your voice holds the secret to making our Xanax kick in faster, we don't want to talk to you.
Of course there are exceptions to all this advice. Maybe your grandparents met when your grandpa honked your grandma's boob on the crosstown local. Maybe one of your friends met her boyfriend when he interrupted her to ask her what she was reading. These things can happen. Furthermore, different people like different things. Follow this list to a T and you still might manage to offend someone — because we all have our own shit going on.
Also, and I know this goes against everything phrenology has told us, but women aren't stupid. In fact, a lot of us are actually pretty good at reading people. If women keep responding to you like you're some weirdo creeper, then chances are that you're acting like a weirdo creeper. The problem is you. On the other hand, if you make an effort to be polite, respect our space and recognize that we don't owe you anything (which, hey, we don't), then we'll pick up on that, too. Does that mean that we'll definitely go out with you? Absolutely not, but it certainly raises your chances and makes you a lot less of an asshole.
TL;DR? Be polite and respect someone's space. The end.