How to Ask Out a Stranger in New York

So, you're out in New York, and you have just found yourself checking out someone really hot on the other side of the room. Ok, first off, stop staring! You don't want to come across as creepy or perverted. I'm going to give you some tips on how to go about asking out this amazingly attractive person that's caught your eye, even though you've never met before in your life. I know it's hard. I know you're scared. Just read this article, do what it says, and remember to breathe.

Make sure they're not married.

Ok, first things first, it's best if you can find out somehow if the person you're thinking about asking on a date is single or not. Do you remember which hand people wear their wedding ring on? Check out the left hand. If there's a gold band on the ring finger or a diamond the size of a walnut, the person's married. You can stop panicking and just be on your way. No point in trying to break up something special, no matter how good looking they may be.

If you can't see the left hand from your vantage point, you'll have to be a little sneaky about it. Most people also wear a watch on the left hand. Pocket your own watch and go ask them if they happen to have the time.

Not yet! Keep reading! You need to know what to do if they're single!

Pick a relevant topic.

If you're going to go up and talk to this hottie, you're going to need something to TALK about! Don't comment on the weather unless it's exceptionally nice or very bad... in fact, even then it's probably not the best way to start things off. Make a quick mental note of what the person is doing while you're checking them out right now. Are they browsing through a particular genre of book? Did they just order an unusual drink? Are they comparing the ripeness of cantaloupes? Good! Use that! Talk about what you see them obviously being interested in. This will show interest and hopefully getting her talking. Try to keep the conversation moving if you can, but it needs to be relatively based on a general theme. For instance, if you start talking about the author of the books she's reading while sipping her wine, bringing up last night's basketball game probably isn't the greatest segue into "Can I buy you dinner sometime."

If you can make her laugh, do.

If the topic wanders to something that you either know an amusing anecdote or you can make a witty, then go ahead and use it. If you can make them laugh (or even genuinely smile) that's bonus points for you! It shows that you're not only funny, but confident enough to be funny around a perfect stranger! But, make sure that it's actually funny before you say it! There's nothing worse than cracking a joke to a stranger that's either totally unfunny or even rude/crude. It could make you seem uncaring or even creepy, and will make them suddenly be "in a bit of a hurry, if you could excuse me."

Don't be creepy!

Don't ask questions that are too personal. "What do you do for a living" is acceptable. "Who do you live with" might be creepy. "That's a really great shirt" is fine. "Do you wear it to bed?" is creepy! Also, don't be a little lapdog. If it's clear that the initial conversation is dying or dead, don't take it upon yourself to start following the person around or standing there awkwardly. Know when it's time to move on.

Don't ask for numbers.

Don't say "Can I get your number". If they want you to have their number, they'll give it to you. Feel free to offer yours, but don't expect them to do the same.

Be Bold!

If things are going well, and you've been talking to this person for a bit, you've got them laughing and comfortable and they aren't trying to make an escape break, then perhaps you should be bold and ask to continue the conversation elsewhere... say, over coffee?

Asking a stranger on a date, if done right, could be charming to the point they can't refuse and intriguing enough for them to be interested. If done incorrectly, you could come off as "some creepy guy that wouldn't leave me alone". Don't be creepy.

Ok. Think you're ready now? Go on over there and strike up a conversation. And remember, be yourself, act natural. Finally, if you really show interest in a person and you are really interested, you can't go wrong.

-Henry Betran for

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