How To Approach A Stranger, Because Sometimes Love Is Waiting Behind The Barista Counter

If you're single, striking up a conversation with a guy or girl you don't know can seem really daunting. Actually, it can seem really daunting whether you're single or not, but if you're single and on the prowl, the desire to do so greatly increases. It can strike at any time: at a reading, at a coffee shop, on the subway, on the street. Although it's true that opening your mouth and saying something absolutely sets you up for the possibility of rejection, it also sets you up for the possibility of a fun conversation. And maybe a date. You never know. It's a risk, but there's actually nothing to lose, so — why not?

I remember this first dawned on me when I was single, and I was at a restaurant with a friend. I kept looking at this guy because he looked just like a dude I knew in high school, and I was trying to figure out if it was him. He wound up coming over and talking to me, and I was so convinced that it was this other guy that I was like, "Thomas??" He was like, "It's Marcello!" And then he turned out to be a weirdo and hit on me. But no worry. I came away from this experience with the realization that it's all about getting a conversation started. Once it starts, if there's attraction and chemistry, the conversation will take care of itself and continue on a natural route, as certain conversations are wont to do. If it's not a good fit, it might be awkward for a moment, but then you can continue on your merry way. So, here are a few possible spots where you might meet an eligible bachelor(ette), and if/when you do, some suggestions as to how to break the proverbial ice. When all else fails, pretend like you recognize the person and be like, "Marcello??"

1. At a reading:

If you know any of the people reading, you can turn to the person you're into and ask if they know the writer you know as well. If it's an event where you know no one, you can casually ask them what their favorite book or article by the writer you came to hear is. Remember: It's just about opening your mouth!

2. At a coffee shop:

If your crush is a barista or waiter at your local haunt, this is tricky, because you don't want to embarrass yourself and not be able to frequent this spot any more. You probably don't want to be so brash as to scrawl your number on the bottom of your receipt and write, in big block letters, "Call me!" But there are ways to finesse the situation, and finesse you should do. Ask if they're doing anything fun this weekend, and see if there's anything in there that you have in common. If they mention they're going for a long bike ride and you're into bikes, you could mention you've been looking for people to bike with and ask if they'd like to take a spin sometime. If they're like, "Nah," no harm, no foul. You can still order a double macchiato with a straight face.

If we're talking just a rando with long eyelashes who's chilling at the next table over, assess the situation. Are they reading a book you've read? Tell them you've read the same book, and ask if they've gotten to your favorite part (without any plot spoilers, obviously). If they're reading something you've never read, never fear: You can ask what it is, because it looks so interesting. It's all about finding an in.

3. At yoga class:

If it's your yoga teacher, proceed with the same caution you'd take with your barista, because we all know it's hard to replace a favorite yoga class. In fact, I'd go with the same technique I'd take with the barista as well: Strike up a conversation, find something you have in common, and see if they'd like to have it a little more in common sometime soon. An added bonus: You already know they love yoga, so you could tell them about a particular class you like or you heard about at another yoga studio, and see if perhaps they'd like to check it out with you sometime. This is all about giving the other person the opportunity to say yes. If they're not down, they'll politely say no. But they might be down! You never know.

4. On public transportation:

The best route: Compliment their shirt/backpack/sneakers/nail polish color/whatever. A compliment is a sneaky way to start a conversation, because everyone loves to be told they look good. From there, you can ask where they got their item of clothing or accessory. If they're not interested in having a conversation, they will politely answer your questions and stop talking. If they're into it, they'll ask you something or the conversation will continue to unfold organically.

If they're reading a book, you can also try the above-mentioned coffee shop book technique.

5. At a bar or a party:

Good news: Most single people at bars and parties want to meet other single people, so half the battle is already won. It can still feel like a tall order to shimmy up to some hot stranger and say, "Sup?" But really, that's all there is to it. Speaking from personal experience, sometimes it's as simple as asking a person what they're doing as they take snapshots of the moon with their best friend on a roof.

6. On an airplane:

This is actually a lot easier than you might think. If you're sitting near someone you find attractive, ask them to help you with your carry-on luggage, or where they got their suitcase, or what they were doing or will be doing in L.A./Tokyo/Milan, or if they have any extra Xanax (joke). People are bored on planes. If they're game for a conversation, they'll bite back. If not, small talk will peter out and you can put on your headphones and enjoy the ride.

7. On the street:

If they have a dog, you're in. Ask if you can pet the dog, ask the dog's name, breed, age, etc. Even if the person turns out to be a bust, you get to pet a dog, so this is a serious win-win situation. If the dog is cuddly, your day has already improved. If the person is talkative, even better.

If they have no dog, but are holding a beverage, you could ask where they got it. When I moved to my neighborhood, I'd see strangers walking by with coffees and thought maybe I'd ask them where the coffee came from, since I couldn't figure out where the coffee shops were at first. (They just turned out to all be at least a five minute walk away.) I actually didn't ask, because I figured it out and I didn't really want to start up a conversation with any of them, but if I had wanted to talk to one of them, I would've had something to say.

Worst case scenario: no dog, no drink. In this case, approaching a person walking down the street is pretty much impossible, which brings me to my final point: You don't have to throw yourself at everyone. If the time is right and the connection is there, it'll happen. Sometimes being single is about summoning your courage, opening your mouth, and not being attached to the outcome. But sometimes it's just about admiring someone from afar and knowing that sometimes other people admire you from afar, and there's a certain magic and mystery to that.

Images: Angie Chung/Flickr; WiffleGif (7)