The En Route Meet-Cute: How to Pick Someone Up on the Subway

subway - mediumLove can happen pretty much anywhere. And your local public transportation system is teeming with love-hungry folks. The train (or subway, or bus, whatever) is a cocktail that’s being shaken around the clock: You never know whom you’ll end up next to or when.

And since you may find yourself on the subway at one point or another, there’s no reason you can’t make a connection there. You don’t need a bartender in range to connect with another single person. So, here are my tips for meeting someone on line—the MTA line, that is.

1. Get within 5 feet of that person. Obviously, you’re not going to yell across a car, especially a crowded one. Work your way into that person’s vicinity, but do it nonchalantly, as opposed to making a beeline, which can come off as aggressive.

2. Make eye contact. Now, granted if this person is staring at their phone, staring them down won’t work and will come off creepy if and when he or she happens to look up. If you DO make eye contact, don’t hold it like a crazy person, but smile and hold their gaze for an extra beat, then look away (this is, of course, Flirting 101). SMILE IS KEY—it registers a connection right away. It says, “I have noticed you.”

3. Initiate a conversation. This is key if there really is no way to make eye contact because s/he’s staring at his phone. And don’t delay. Time on a train is limited, and he who hesitates is lost. The longer you wait, the more likely you are to lose your nerve. Resist the urge to script your conversation preliminarily, because that’ll create more mental obstacles. Just start it, and let it go where it goes.

Now, the initiation has to feel natural to you. And so I offer you a few options, and what feels most natural to you will depend on your personality type. The idea that you “can’t” start a convo b/c: you’re introverted, shy, a girl—all that is garbage. You don’t need to be some alpha dude to start a harmless convo.

a) The question. This is the most harmless way to break through the stranger-veneer is to simply ask something. You don’t have to pretend to be a tourist (bad idea to lie) to ask a simple question (I do it all the time, for reals). “Hey, do you know if this goes to Wall Street” or “Do you live in this area? Would you happen to know if…” fill in the blank.

This serves two purposes: one, it breaks thru the silence and establishes contact, but it also puts the other person in the position of confidence and power because you are asking for their help. Trust me, this is key. I’ve had people ask me as I’m reading my Kindle, “So, what do you think of that Kindle?” and I am happy to talk about it.

b) The compliment. Flattery will get you everywhere, or at least, most places. It’s true. The hottest girl and even the most styling dude can’t get enough of them, nor can the rest of us. But there’s a right and wrong way, and there is a gender breakdown.


Cute girls will be on guard, because they know that compliments, while nice, can raise a flag and we wonder “What does he want?” So avoid anything that makes them feel put on the spot in a weird way, like “You have such beautiful eyes” or the like. Don’t make it sound like a line. Give a genuine compliment and give it with no strings attached. I’ve heard women say they don’t like when someone compliments a THING they have/own (“Who makes those cool shoes”) because then it’s more about the item than, well us. But I still think it’s ok, as long as it’s a genuine compliment, and I’m in there somewhere (“Cool shoes. They look great on you.”)


Men don’t get complimented all that much (maybe ever, especially by strangers), and they want them as much as anyone. So you kinda can’t go wrong here. A genuine, friendly compliment on just about anything will open a guy right up. In this case, I DO think complimenting a guy on what he is wearing/has is key because it not only says you noticed, but confirms his good taste. Ladies, you have it easy.

I will underscore this next point: DO NOT give a weirdo pickup line. I shouldn’t even have to say that. For this to work, it has to sound like genuine, spontaneous conversation.

c) The shared moment. Crazy stuff happens on the train. When it does, I consider it a gift from the subway gods. Use it. A mariachi band comes on at 8:30am in full regalia. A crazy person starts singing opera on the L. A couple starts yelling at each other. Who knows. If it happens, it’s a great opportunity to connect with this person in a way that is memorable, because it’s something you experienced together.

This is where humor really comes into play, and if you happen to be funny, witty, or observant in any way, this is the time to strike. You can make eye contact, roll your eyes, and say something like, “Man, I can’t stand mariachi in the morning. I prefer it on an evening train, during happy hour, don’t you?” You don’t have to be Louis CK to make someone laugh to get a response. It’s often a great tension breaker, and people get nervous on the train.

4. Move the conversation along. You established contact. Great! Now, move past whatever sparked the convo (the Kindle, the great shoes, etc) to real conversation. Unless all you really wanted was a consumer review of e-readers, and I doubt that. Nor is it really a shoe conversation. You want to see if you could connect with this person in a real way. Here’s where you can say something like, “You look familiar. I’m sure I’ve seen you on this train before. Do you work downtown? Yeah? What do you do?” And you’re off to the races.

5. Get a name, a number, website, a Twitter handle, anything. Remember, the goal here is not to have restaurant reservations or know her life story before you reach 72nd street, but to establish some kind of connection so that you can be in touch once you part ways. That and that alone is the goal of an en route meet-cute.

Ladies, you can do this as well as a guy can. You can say lots of things besides, “Can I get your number,” which for some reason, I’ve never liked. It sounds like you’re asking for a handout, unearned. The key is to make sure that person knows you’re interested in him or her. You must take the risk here and let someone know you’re interested in THEM, and while I know that’s the most terrifying part, all of this is worth nothing if you don’t do it.

Some options:

“I’d love to see you more than just by accident. Want to get coffee sometime?” or “Well, look, you seem really cool and I’d love to see you again, but on purpose. Can we stay in touch?” See? Harmless. Men, I’d offer your card if you have one but also get her info (whichever way she prefers—email, text, Twitter, whatever). You can take a moment to key each other’s info into your phones, but the problem is if you forget that person’s name, good luck finding it. Again, time is of the essence.

Ladies: I see no harm at all in offering a card—a biz card is fine, but it’s not a bad idea to have basic contact or ‘calling’ cards as they used to be called that has the info you want to share on them. Bottom line here, if you feel weird asking a guy for his number, etc, I like offering a card and saying, “Email me if you’d like to get together sometime.” I’ve done it many times to strangers I’ve met—some called, others didn’t. No harm, no foul. One did. That was all that mattered.

(Check out more advice on subway meet-cutes in this story on dnainfo.)