Let’s face it: Some of us struggle to put together a date night worth remembering. And with Valentine’s Day around the corner, the pressure’s on. But don’t worry! Whether you’re meeting someone for the first time or looking to spice things up with your ride-or-die, C-VILLE has you covered.
We consulted local matchmakers Olivia and Jess Gabbay to come up with some creative date night ideas. They started Matchbook Charlottesville last summer—a free, seasonal matchmaking service that, in its first season, set up more than 120 people on first dates. Here are some of Olivia and Jess’ favorite spots.
First date
First dates are as exhilarating as they are nerve-racking, so we suggest a fun activity to take some of the pressure off. Maybe go roller skating at the Carver Recreation Center—which is totally free and includes skates—take a walk through the oak trees at Forest Hills Park, or bicycle the Rivanna Trail.
“Arrive curious and a little playful. You’re just trying to see if you want to spend more time together.”
—Olivia & Jess
Valentine’s Day
If you’re reading this, you probably haven’t made any reservations yet. Securing a table at Charlottesville’s most romantic spots might be a crapshoot at this point, so why not cook up something special at home? Foods of All Nations has spices and sauces that can transport you anywhere. Even if you’re not much of a cook, it’s the thought that counts.
“Be sure to preorder flowers at Hedge Fine Blooms! They offer a ‘Pick Your Own Stem’ bar and sell beautiful vases.”
—Olivia & Jess
Anniversary
No matter how many years have passed, marking your relationship’s milestones is your opportunity to really wow your partner and show how much you cherish the life you’ve built together. Sweets are a perennial winner, so splurge on a decadent gift box at Gearharts Fine Chocolates or share something at the downtown shop’s dessert café. If you both want a hand in making a meal, we recommend reserving spots for a cooking class at The Happy Cook to surprise your S.O.
“If you want to go classic, everyone looks great in the warm lighting at Tavola or The Alley Light, and why not look hot and eat amazing food on your special day?”
—Olivia & Jess
Friends dates
Not every date night has to be hot and heavy. Some of us just want to hang out. If you’re looking to spruce up a friends’ night in, the kind and knowledgeable staff at Market Street Wine can point you to the perfect vino to share—plus, they host free wine tastings on Wednesdays and Fridays. Pick up the group’s favorite bottle and one of the shop’s puzzles to do at home, then pit stop at Luce to grab pasta to pair it with.
“If a puzzle at home feels a little too cozy, get competitive at Decades Arcade.”
—Olivia & Jess
Show date
Hit the Downtown Mall for one of the many shows at Live Arts or The Paramount Theater. If you want to take in a movie, especially one a bit more indie, Violet Crown Cinema has you covered. Afterwards, you can debrief over ice cream at Chaps.
“It’s exciting to learn more about how the person you’re dating thinks—you might just be surprised by their ice cream choice, too.”
—Olivia & Jess
Artsy Saturday
Never underestimate the romance of an art walk. Charlottesville’s wealth of art galleries, with rotating exhibitions, offer feasts for the imagination and fodder for great conversation. Check out New City Arts, Visible Records, McGuffey Art Center, or The Fralin—or make a day of it. Get coffee, and visit all four.
“Start the day off right with your favorite espresso drink and a pastry at Lone Light.”
—Olivia & Jess
Outdoorsy dates
With the up and down weather these days, you and your date might have a surprisingly warm afternoon to plan around. Plus, Punxsutawney Phil predicted an early spring, so it might be wise to start brainstorming picnics and trail walks now. We recommend Ivy Creek Natural Area or Darden Towe Park for bird and people watching, with the added benefit of being near the water.
“If you want to be more active, a day pass at Rocky Top can fill that ‘outdoorsy’ urge in the wintertime.”
—Olivia & Jess
Book date
The Downtown Mall is lined with great bookshops to visit, from the resplendent New Dominion to the trans-owned antifascist The Beautiful Idea. And don’t forget the Central Library. Wherever you go, take some time to explore, and grab a book your date will love. All of these spots also host free events, so be sure to check their calendars for more date ideas.
“It’s extra fun to recommend each other a book and cozy up at Twisted Branch Tea Bazaar afterwards.”
—Olivia & Jess
