Statistically speaking, there's a pretty good chance if you don't already work in the Flatiron area, you will eventually have to organize some sort of drinks gathering in the Flatiron area. Whether you're catching up one-on-one, have gotten stuck planning a coworker's big group going away party, or just want to find a kind of crappy bar with cheap drinks, we've got you covered.
We've broken it up based on size of the group you're rolling with. Also, for the sake of this exercise, we've extended the western boundary of Flatiron to 7th Avenue. Now go enjoy yourselves.
Casting directors looking for a real "speakeasy" for the date scene in your romantic comedy, check out Raines Law Room. They do the whole shebang: an unmarked door, dark and low ceilings, plush old-timey couches, and of course, fancy cocktails. Naturally, a good spot for a one-on-one.
A relatively non-descript, but very useful modern-looking wine bar on 7th Avenue. In addition to wine and cocktails, they do easy little Italian small plates and paninis. We've been on both job interviews and dates here.
This place serves a similar purpose as Veloce, but on Broadway, if you need an option a few blocks further east. It's connected to a relatively corny restaurant below called Punch, which you should avoid. However, although its name might suggest differently, Wined Up is a nice spot where you can actually hear the person you're talking to.
The Clocktower, on the second floor of The Edition hotel, is a great new restaurant to have dinner - due in part to the fantastic room. But it's also a nice spot for a drink - settle into the bar room on the early side.
The brewery-style rooftop of Eataly exists. Don't forget it. Make a reservation for a small group to keep things stress- and wait-free.
A Belgian restaurant on 21st and 6th, Markt's Belgian beer selection and lack of crowds make it a perfectly suitable choice for a little group drinks gathering.
Bo's Kitchen & Bar Room6 W 24th St
A nice Southern-inspired restaurant, Bo's is a solid choice for dinner, but we use it most for getting together with a few people in the nice downstairs bar room.
Right off Madison Square Park, hit Live Bait for a cheap happy hour in a kitschy Cajun-themed bar. If you're looking for a well-crafted Manhattan, head elsewhere (also, chill out) - this is a sh*tty margaritas and shots of well whiskey kind of spot.
Flatiron Hall38 W 26th St
Flatiron Hall is run by the same people behind Houston Hall, the massive Soho beer garden that feels somewhere in between Oktoberfest and a tailgate on a Saturday. Think of this space, which looks like one of those nice old fraternity houses, as the more buttoned-up workday version. Get a stein of beer, naturally.
Belgian Beer Café220 5th Ave
More #beer. Belgian Beer Cafe is exactly what it sounds like: a two-floor restaurant and bar focused on Belgian beer.
Yes, there's a Barcade on 24th Street. Take the dev team here and emerge a hero.
The theme of the bar is quite literally "one star on Yelp." The self-awareness sort of works perfectly: it's non-descript, kind of cheap but not that cheap, and probably everyone is drinking a serviceable but watery whiskey ginger. Take your coworkers here and everyone will inevitably complain about it relentlessly, but will also end up here once a week.