After months of swiping, messaging, Instagram lurking, and bargaining with a higher power, you finally did it - you’re going on a first date. But that also means you have to do that thing where you meet a complete stranger and attempt to convince them that you are a cool, stable person who’s worthy of love and affection. To pull that off, it helps to have alcohol. Preferably at a bar that’s not so fancy it’s uncomfortable, not so loud you have to shout, and not so quiet you can hear the other person regretting this decision. Oh, and it wouldn’t hurt if that bar also has delicious drinks and a decent food menu, either. It’s a tall order, but we have some ideas.
Key Biscayne's Vinya is the kind of casual-yet-fancy wine bar that'll really help you nail the "I'm trying, but not too hard" messaging of a first date. There's indoor, outdoor, and bar seating that's all walk-in friendly. The wine selection is, obviously, great (with glasses for as low as $8). They also have excellent cocktails and beer too. But the food here is so much better than your average wine bar charcuterie. There are small plates, salads (including a gorgeous niçoise), and bigger entrees, like lobster thermidor sitting in a delicious gruyère sauce you get to mop up with slices of toasted brioche. It's never too loud to have a conversation inside, the service is attentive (but not suffocating), and it's pretty close to the beach in case you want the date to end in a sunset stroll, because you're just romantic like that.
The NIU Kitchen team’s latest pivot, NIU Wine, has almost immediately become our favorite spot in town for a date night. The narrow space has an intimate dinner party energy, a noise level that’s perfect for conversation, and lots of candlelight, which will elegantly conceal the pimple that sprung to life six hours before your date. There’s not really a wine menu here. You just chat with the owner and she’ll bring you some bottles to try. But there is a rotating food menu, and it’s full of wine bar appropriate tapas like bacalhau with sofrito aioli, charcuterie, and a spiced chocolate truffle you definitely want alongside a glass of that red you picked because you liked the label.
The Sylvester feels like the living room of your aunt who never misses a good estate sale. So there are plenty of comfortable spots to sit and have a conversation among the mismatched furniture at this Midtown bar. Also, the cocktails here are great and so is the food, which includes small things like empanadas and larger things like a pastrami medianoche. They also have a pool table, in case you want to impress your date with your pool skills and/or let them win in what will surely be an irresistible display of vulnerability. Also, they do accept reservations online, in case you also want to demonstrate how organized and prepared you are.
If the president gathered a team of NASA’s top scientists and ordered them to build the perfect first date bar, you’d get Margot. The narrow Downtown spot is a very romantic shade of pink, has lots of natural wine options, and can simply be described with no word other than “cozy.” Plus, there are very tasty small plates you can eat without making a mess - like crudo, marinated olives, and a big pile of ham and potato chips. (That last one might actually be a little messy, but it’s also worth it.) Before you plan a date here, we should warn you that this place is popular and doesn’t take reservations, so try to come at an off-time, or risk waiting 40 sober minutes for a seat, which is a first-date worst-case scenario.
Casa Florida is one of our favorite places to drink outside, because it has a lovely, spread-out space, solid cocktails, and feels secluded even though it’s just across the river from The Wharf. Your date will (hopefully) appreciate all of these things, including the retro bus that’s been repurposed into additional seating. Maybe you can hide in there if it starts raining. That sounds like a cute story you could tell the kids one day, huh?
For something a little more intimate, go to Swizzle in South Beach. We really love this bar, mostly for their stellar cocktails, but also because it feels like a basement bar (even though it’s only three steps below sea level) and we so rarely get the chance to feel like we’re drinking underground in Miami. Even though it’s in a touristy part of South Beach most locals vow never to step foot in, this place still feels like a secret and it’s not so loud that you can’t have a conversation. They have outdoor seating too, in case you’re feeling a little claustrophobic inside.
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If your idea of a perfect date involves tinned fish and wine, then you should come to Paradis Books & Bread. The excellent little North Miami spot straddles the line between bar and restaurant. They serve things like sardines with seaweed butter and slices of fresh bread, excellent pizza by the slice, and plenty of wine, both by the glass and by the bottle. It’s a lowkey, quiet spot where you’ll have no trouble hearing your date, who will assume you’re very cultured since you brought them to a bar with lots of books. You don’t have to tell them it took you’re currently re-reading Harry Potter for the ninth time.
Jaguar Sun is a little different than it used to be. Whereas before it was an even split between a bar and restaurant, the Downtown spot feels more like a bar now. They've closed the dining room and are only using the bar area. They aren't taking reservations either, so seats are a precious resource and (unless you come very early) you'll probably have to wait. The good news: they're still serving the same great cocktails they always have. And there is also still food, courtesy of Gilda, a pop-up serving really delicious Basque pintxos. They have all sorts of oily fish perfect for bar snacking as well as slightly more substantial things like meatballs and a bikini, which is a fantastic, crispy sandwich stuffed with ham, cheese, apple butter, and black truffle.
Abbey Brewing Company
The Abbey isn’t a first date spot for everyone. It’s on the dive bar end of the spectrum - although not at the extreme end. But if your date appreciates an old school bar with lots of charm, then go for it. Despite being just off Lincoln Road, The Abbey feels like a local’s spot. The staff is friendly, they have darts and pool, and you can sit in these adorable little mini booths perfect for couples. The Abbey feels more vaguely European than South Beach, and could make for a delightful change of pace if you’ve spent the last seven first-dates at Lagniappe.
Taking a date to Gramps is like having them meet your best friend, or your dog. If they don’t like it, it was probably never going to work out. Because what’s not to like about Gramps? It’s a tropical bar that blends old Florida dive-i-ness with the atmosphere of a modern cocktail bar. The drinks are awesome, they sell great pizza by-the-slice, and the music is always on point. Because you are in Wynwood, weekend nights can get a little crowded and loud. Weekends are more subdued and first-date-friendly, except for the (very fun) Thursday Double Stubble party.
Speaking of Lagniappe: Lagniappe. Is it a bit of a first-date cliche? Yes. But is it also still a really lovely spot to enjoy a bottle of wine and some cheese outside? Absolutely. The hardest part about planning a date here is the uncertainty of whether or not you’ll be able to find a table in the always-crowded backyard. So, this is another place where you’ll want to come during an off time, or pay a friend $15 to arrive 45 minutes before you to claim your table.
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There’s nothing too complicated going on at Lost Boy, which is why we love it for a first date. This place is pretty casual, but not at all divey. Grab a seat at the long bar, order a gin and tonic, and enjoy a noise level several merciful decibels below most of the surrounding Downtown bars. This is a great call for both a post-work Happy Hour or a post-9pm meet-up.
Sweet Liberty should always be high on the list for date night consideration, because there really is no downside to coming here. They make some of the best cocktails in the city, have a solid kitchen serving things like oysters or caviar onion dip with house-made potato chips, and the service is always on point. So even if your date won’t stop talking about their high school football career, you’ll at least have something delicious to distract you from the regrettable realities of online dating.
Mini Bar is a rare kind of cocktail bar for South Beach. It has a local crowd (despite technically being a hotel bar), is small but rarely overcrowded, and serves pretty good cocktails that don’t cost $18. So it definitely deserves to be on your roster of potential date spots. There are some outdoor tables where you can hang out on a nice day, but we really like sitting at the bar here, which pretty much takes up the entire space. And if things are going much better than you expected, see if you can get a table at Orilla next door for dinner.