15 First Date Spots To Eat, Drink, & Say Something Embarrassing

These Philly cafes, bars, and restaurants won’t be the reason your date is awkward.
This is an interior shot of Toska Restaurant & Brewery.

photo credit: NICOLE GUGLIELMO

First meetups are a mixed bag. They can be nervous coffee exchanges about favorite movies or wine-fueled rants until you call it quits or maybe jump each other’s bones. Dates are always going to be a little chaotic, but they should also be fun. So we put together a list of coffee shops, bars, and not-too-formal restaurants where you'll be in a good space to get to know each other, play a game if that's your thing, or simply drink one negroni and bounce. Even if the person you're with spends 20 minutes talking about Delaware's tax perks, you can sleep soundly knowing the date spot you suggested wasn't the problem.


Snacks & Drinks

photo credit: Gab Bonghi



$$$$Perfect For:Drinking Good WineSmall PlatesDrinking Good CocktailsFirst/Early in the Game DatesDate NightCatching Up With Mates
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The thing about this wine bar in Rittenhouse is that you can be in and out within an hour and not look like a classless monster. This is somewhere you go to drink something interesting, pick at steak tartare, and spend 45 minutes confirming that your date is familiar with the concept of empathy. The bar has a tight by-the-glass list, so you won't have to fumble through dozens of options. If your date takes out their phone to shoot a video of the egg served with the tartare and then gets distracted by their "very important texts," shorten the experience to 35 minutes.



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Several questions remain regarding the photo of your date doing body shots at a tailgate. (Why would they post this? Are you attracted to the image in an upsetting, dirtbag kind of way?) There's only one way to get answers: a subtle interrogation over mezcal margaritas. Whether you’re inside or outside, the casualness of this South Philly Mexican restaurant will help you get to know someone quickly and without high stakes. The food, like al pastor tacos or some very good shrimp, is all pretty light. So you’ll still have the energy to go dancing, bar hopping, or swipe right on a dating app if the conversation sucks. 

Save your favorite old-school Italian restaurant for date number four. This first meet-up should be more about atmosphere and drinks than white tablecloths and good veal parm. Queen Village’s Cry Baby Pasta has soft neon lighting and a banner that reads “I’m so tired of being good” on the walls. In other words, it's a little sexy but not too serious. The spicy artichoke bruschetta and pumpkin spice sformato won’t alter your world, but the well-made cocktails, like Luna Rossa and the Rosa Negroni, make up for it. 


Fishtown’s Next of Kin is open late, which makes it a good option for a first date when the person is hot but you know the relationship isn’t going anywhere except your apartment a few times. The space is properly dark (so many Philly bars aren't) and not pretentious at all. Drink a well-made banana daiquiri or a Penicillin. There's no food available at the bar, but you're not dating this person so you can eat well or have invigorating conversations.

There’s no better setting for rambling off the useless information in your head than at a vinyl bar with good cocktails. Because when you’re in a place that plays obscure jazz and legendary albums, you just seem 70% cooler. This Old City bar also has a fireplace where you can sip cocktails overlooking Second Street. They don’t serve food, but you can always start downstairs at Sassafras (from the same people) if you want cheddar curds before heading up and telling them how great they look over Wu-Tang.  

photo credit: NICOLE GUGLIELMO

This is an interior shot of Toska Restaurant & Brewery.

Töska Restaurant & Brewery



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Choosing the right brewery for a date could be the difference between the kind of night the Hallmark channel would exploit or you eating ice cream on the couch alone next weekend. So if you'd like to prove that you're chill and drink beer but you also want a setting that looks a bit nicer than an industrial plant, go to Toska in Mt. Airy. Their dining room has glowing, hanging lights that make the place feel moody but not cheesy. If you get hungry, order a wood-fired pizza, and smoked wings with house hot sauce that will inevitably end up on your shirt.

A first date could easily be ruined by a friend or a neighbor walking in, seeing you, and turning a quick hello into an impromptu group date. This is a scenario that will never happen at a random, regular-ass bar like Grace Tavern in Fitler Square (except maybe on Wednesday trivia nights). Don’t underestimate the power of a random, regular-ass bar—especially one that’s three notches cleaner than a typical dive and has friendly, funny bartenders.


Ray Cafe in Chinatown is a place where you can enact the greatest romantic gesture of our modern age: offering someone the last dumpling. The Chinese daytime shop always feels relaxed, which will take the pressure off. They also serve some of our favorite food in the neighborhood. Order a siphon coffee, order some rare tea, but whatever you do, convince your date to split a dumpling sampler and then get your own bowls of beef noodle soup.

Callowhill’s Elixir's roastery is the largest of all three locations. So, you won’t have to worry about being squeezed or sitting super close to other people when you're answering not-so-subtle questions about your dating history. There's a good selection of bagels, espresso, and lattes with foamy art. The most likely way you'll feel disappointed here is if the date lied about their height or their love of the Eagles on the apps. 

This bakery on the first floor of the Bok Building works for a low-commitment situation in South Philly. And, even if your date arrives and doesn’t compliment your outfit, you’ll at least get to eat a flaky apple danish next to a big window. You could always wander around the shops on the first floor if they start talking about birth charts. Or, if things are going well, stick around for a few hours after Machine Shop closes and head to Irwin’s or Bok Bar on the eighth floor. 

When choosing a first date spot, you want to give off the impression that you know about great places in Philly but you’re not high maintenance. That’s Jezabel’s in a nutshell. This Argentinian cafe in West Philly specializes in baked empanadas stuffed with beef, juicy chicken, tangy root vegetables. They’re all delicious, and the room isn’t too loud, so you can share secrets or start planning the wedding in peace.  

The thing about a daytime coffee date is that you can get to know someone without any stiffness that comes with being asked if you prefer tap or bottled water. At Càphê Roasters in Kensington, you can sit on a couch and split a bánh mí. The big Vietnamese cafe space is lined with plants and books, so you can talk about your dealbreakers or maybe just how you can’t keep a succulent alive while sipping on a frothy egg coffee. 


Forget life stories, the best way to get to know someone is by mercilessly destroying them in Connect Four. At the board game bar in Society Hill, you can have a glass of wine or a beer and decide if you want to see someone again based on how they behave during Battleship. It's the kind of place where you could wear something comfortable and decidedly not talk about your exes. They also serve a bunch of decent vegan food—we like the kimchi burgers and agave barbecue-glazed brussels sprouts—through midnight on the weekends.

Large lawn games can take the edge off of an awkward situation. We get it. If you're looking to play mini golf or oversized Jenga in a setting that’s more exciting than a basic picnic date, go to Libertee Grounds in Spring Garden. They serve drinks, as well as surprisingly good Southeast Asian food like a lamb cheesesteak and a crispy Laotian rice roll. Both should get you through the occasional lull in conversation. And with games like Cards Against Humanity on standby near the golf course, you’ll have distractions when you can’t think of a hobby that makes you sound charming. 

Something Sort Of Unhinged

Stay with us on this one. The Giant by the Schuylkill on 23rd Street has a rooftop seating area with oddly nice sunset views. You can hang out there for the price of a cheap six-pack or a random bottle of wine from the booze section of the grocery store. It’s a plan that's just weird enough to work (and inexpensive enough to ease your upsetness if the date bombs). We’re not suggesting you eat from the hot food station at the supermarket. If you get hungry and things are going well, go to Thanal down the street and eat some tandoori shrimp that tastes smoky after being marinated in curry and chili powder. 

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