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.
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.
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.
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.
Jaguar Sun has officially moved back into its Downtown dining room after a year of outdoor pandemic pop-ups, which we thoroughly enjoyed. Luckily, we also thoroughly enjoy the original Jaguar Sun, which has always been a go-to date spot for us. There are two ways to do Jaguar Sun for a date. Make a reservation and have a proper sit-down experience with great cocktails and pasta. Or, walk in and try to snag a couple seats at the bar to enjoy said great cocktails, and maybe something to share like the excellent Parker House rolls or oysters. Just know that trying to walk in might be risky, since this place is small and seems to be getting more popular by the hour, like tinned fish or Steven Yeun.
Abbey Brewing Company
The Abbey isn’t a first date spot for everyone. To start, you can smoke in this South Beach bar, which means you will both inevitably leave smelling like the Marlboro Man. It’s also on the dive bar end of the spectrum - although not at the extreme end. But if your date appreciates an old school bar or they were vaping in one of their profile pictures, 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.
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.
Spanglish is a small cocktail bar in Wynwood that works for a slightly more energetic, upbeat first date. This place is by no means a club, but they will occasionally have a DJ and music that will require you to raise your voice slightly. Still, it’s a stylish place with murals that aren’t corny and lighting that’ll make you look 60% more attractive. Also, the cocktails here are very good, especially the Old Fashioned that gets poured from a bright red cafetera.
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.