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Whether you’re on a first-time Bumble date or practically on your way down the aisle, your time is too precious to waste on a boring outing. That’s why we’ve put together five foolproof date scenarios perfect for whatever relationship stage you’re in. Let’s just say you’re winning the dating the game.

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wynwood miami
Courtesy of KYU

When You’re Meeting For the First Time: Wynwood

If you’re looking for a laid-back place to meet someone, plan your date in Wynwood. Arrive a half hour before sunset, which is the absolute best time for exploring the neighborhood’s many graffiti-clad walls. Walk up and down the main strip on NW Second Avenue and pop into a few open galleries. By 6:30 p.m., make your way to the rooftop bar No. 3 Social for a fancy drink or a boozy ice pop before an 8 p.m. reservation at KYU, a wood-fired restaurant known for its Japanese barbecue-style eats and dimly lit vibe. After dinner, head across the street to Wood Tavern for a casual beer, a game of giant Jenga and live music.

upper buena vista miami
Courtesy of Vista

For a Second or Third Date: Upper Buena Vista

Surrounded by large banyan trees, Upper Buena Vista has all the fixings for a perfect (and quiet!) afternoon-into-evening date. This serene enclave is filled with local shops, restaurants and the area’s first rooftop bar. (Hint: That’s where you’ll end the night.) First, stroll through the micro-boutiques, stocked with everything from bohemian clothing to sunglasses tohome goods. Once you’re both hungry, claim a table at Vista, a modern Italian restaurant. Order a bottle of wine and enjoy conversation over a charcuterie and cheese board and pistachio-mint gnocchi. Keep the night going at Vista’s rooftop bar, which offers music and a spate of drinks (wine, beer, cocktails) to enjoy while gazing at the unobstructed views of the downtown skyline.

kaido miami
Courtesy of Kaido

When You’re Approaching the ‘What Are We?’ Stage: The Design District

When you and your date are ready to take your relationship to the next level, it’s time for an evening in the Design District. The pedestrian-friendly area is filled with art, restaurants and shops. Arrive just after 7:30 p.m. for dinner at Swan, a modern American-French restaurant by hospitality vet David Grutman and Pharrell Williams. It’s one of the most gorgeous restaurants to open in the past year and the food is next-level. (Order the “Corn Corn Corn,” a creamy polenta and popcorn dish, and a bowl of caviar spaghetti.) When you’re finished, stroll through the open-air mall and make your way to Brad Kilgore’s Kaido, a swank Japanese-inspired cocktail lounge with high-end drinks and small bites. While you may not be hungry, nurse a cocktail at the bar or sit outside near the DJ.

west palm beach
Courtesy of the food hall

When You’re Both Sick of Miami: West Palm Beach

When you’ve exhausted every Miami hangout option and you’re ready to go on an adventure—not necessarily a multiday trip, but somewhere you can spend an entire day—drive north to West Palm Beach. From the world-class art and history museums to the gorgeous beaches and stellar restaurants, this Florida town is the perfect place to bond and enjoy each other’s company. Start with a tour of oil tycoon Henry Flagler’s 100,000-square-foot Gilded Age mansion, Whitehall. Then explore the outdoor grounds of the Norton House, which includes 250 tropical plants and 100 different sculpture works. In addition, make sure to have a cocktail at The Breakers and embark on your own personal food tour inside Palm Beach’s first-ever food hall, Grandview Public Market. We’ll take a fried chicken sandwich and some wine at Clare’s, followed by Thai rolled ice cream at Crema.

Jeff Greenberg   Getty Images
Jeff Greenberg/Getty Images


You’ve been dating for a few months, you’ve met each other’s friends and you’re even planning a summer vacation in Cabo. But when it comes to date night, you’ve run out of things to do, which means it’s time to get creative. You don’t have time to go far, but you want something that’s romantic and fresh. Enter Sunset Harbour, a charming neighborhood in South Beach. This relaxed area offers minimal crowds, pristine beaches and delicious detours. Start with a late lunch at Dirt, a farm-to-counter fast-casual eatery replete with fresh salads, wraps and bowls. Then set up beach towels in South Pointe Park and relax with books and a bottle of wine. Once the sun sets, grab dinner at Joe’s Take Away. We’re thinking stone crabs (it’s the season, after all) and, of course, key lime pie.

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