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Photograph: Courtesy Creative Commons/Flickr/christine kaelin

14 people you'll definitely go on awkward dates with in New York

Will Gleason
Written by
Will Gleason
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1. The NYU Film Grad
He's making films and really wants to tell you about them and will maybe even pulls out his phone and forces you to watch for 8 minutes at the table. The film is either an adaptation of a short story about snow or a gay web series.

2. The Brooklyn Bartender
He takes you to his favorite bar and you both get free drinks, but pretty soon he's too drunk to hold a real conversation, and not in a fun way, and you get the feeling that's the norm for this guy.

3. The DIY Obsessive
She dominates conversation talking about how she pickles this weird food or makes nonsense objects out of trash.

4. The Literary Scenester
Does this guy seriously not know it's rude to insist on talking about obscure literature for an hour, or to ask you point blank if you're ready to fall in love again?

5. The Real Estate Broker
He regularly checks his phone during the date, because making a deal is more important than not being alone for the rest of his life. He also judges the neighborhood you live in and explains to you why you shouldn’t live there.

6. The Murray Hill Man-Child
He spends most of the date telling you disgusting stories from his frat-bro days, and they obviously haven't ended even though he's been out of college for four years.

7. The Equinox Trainer
Words are hard. (But so are his abs.)

8. The Wrong Date
Every bar in New York is so packed with first dates every night of the week, it’s easy to sit down with someone who kinda, sorta looks like the person you’ve been talking to on Tinder, and it takes about 15 minutes registering all the details that don’t make sense to realize your actual date is the girl over there staring at you funny. 

9. The Urban Loner
He’s so desperate for human connection, 10 minutes in he proclaims, “You’re going to be my girlfriend!” Assuring that you won’t be. 

10. The Frugal Finance Guy
He has a gigantic salary and he still makes you split Shake Shack.

11. The Restaurant Regular
He takes you to his favorite spot in the West Village, and knows all of the waiters’ names. He does it to impress you, but the way the bartender is staring at you, you’re pretty sure you’re just the flavor of the week.  

13. The Recent New York Transplant
She’s so nice it turns you off.

14. The Blog Editor or Stand-Up Comedian
You can’t get over the sneaking suspicion that you may just be fodder for a future personal essay, stand-up act or, um… a dating listicle.

By Time Out New York contributors, edited by Will Pulos

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