Sex on Friday

17 Bad Decision First Dates in NYC

So, you're playing the Nintendo Punch-Out!! game that is Tindering in NYC, and it's come time for the in-person meet-up -- known in some parts as a "first date."

You remember that Vince Vaughn line from Wedding Crashers: “And all the while you're just really wondering are we gonna get hopped up enough to make some bad decisions?” More often that not, that's what results from first dates in New York. Bad decision first dates don't always lead to those kinds of decisions -- although, truthfully, a lot of them do. Some will just lead to irrevocable awkwardness that destroys any hope of lasting love (looking at you, couple who decided to bike to the Cloisters on a first date).

The worst part is that bad decision first dates can be hard to identify, as they masquerade as pretty solid dates on paper (or that Tinder chat box). So it’s in your best interest to peep the 17 you should be wary of, because they don’t always yield the expected results -- except happy hour at Niagara, that’s always exactly what you expect.

Drinks on someone’s rooftop

Their bed is, like, right there.

A brewery tour and/or wine tasting

Those cups may be tiny, but it hardly matters when you fill and then down their contents 100 times.  

Netflix and chill

The modern-day equivalent of “make it a Blockbuster night” still means getting it on, by the way.

A lobster dinner cruise if you’re prone to getting seasick

You know the scene from The 40-Year-Old Virgin in which Leslie Mann pukes fish sandwiches on Steve Carell? Yeah, it’s gross.

A bar that doesn’t serve food

Skipping dinner and going right into drinking equals incalculable bad decisions.

Or day drinking without a food break

If you remember, we’ve gone into great detail about why this is a bad idea.

Hiking upstate if you don’t really hike

It will be especially awkward if you bragged about how many spin classes you take a week, and you can’t even make it up Bear Mountain... let alone down it.

Really anything upstate if you don’t know the person all that well yet

How’s that long, awkward trek back to the city?

Biking to The Cloisters

You know you gotta bike back, right?

Drinks at your home-base bar

True story: one time I took a date to my favorite local bar. Due to my friendships with the staff, I was a tad over-served. Next thing I know, I’ve excused myself from the date, and am writing my number on a napkin and not-so-stealthily sliding it across the bar to the bartender. Then, I made out with my actual date. This is now brought up every time I return to this spot. I repeat: do not go on a date to your home-base bar.  

A sporting event if you’re actually pretty serious fans

You’re a diehard Jets fan, she bleeds Buffalo blue and red. This could honestly go way beyond playful competition, and turn into both of you wanting to punch the other in the face. It will suck even more when the girl actually does this.

A super-romantic NYC date

Perhaps you start your night off at one of these romantic rooftop bars, then get swept up in the city’s palpable romance as you stroll hand-in-hand through Gramercy and talk about the dream townhouse you’ll share one day. But first, you should start with something sensible and close to work. Wait, did you just agree to move in together?  

An office holiday party

Two words: open bar. Two more words: your boss.

An all-day music festival

You’re going to try a “special” brownie. And things are going to get really weird for both of you pretty damn quick, depending on how “special” it was.

A food festival

That last cheddar-smothered brat just didn’t sit well, and well, you’re still in the middle of a food festival with no actual bathroom in sight.

Bottomless brunch

That’s not the only thing that will be “bottomless,” amirite?

Happy hour at Niagara

Every $3 beer comes with a shot. No good is coming from this. Ever.

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Liz Newman is a freelance writer for Thrillist and has vowed to never return to Niagara happy hour, until undefeated at the penis game. Follow her on Instagram at @lizn813.