Date night ideas for every type of Lexingtonian

Kids, this is the story of how I met your mother, and it was all thanks to LEXtoday.

Ok, so maybe that’s not exactly how the 2000s sitcom went, but if Ted Mosby had consulted us for date night ideas, we could’ve shaved the show down to two seasons. Whether you’ve met “the one” or are hoping to impress someone new, we’ve got 20+ local date night ideas that are legen — wait for it — dary.

For the ones who want a night out on the town

• If your loved one is a fan of the arts, see what’s happening on stage at the Lexington Opera House or Singletary Center. Pro tip: Stop in across the street from the Opera House to Agave & Rye for a pre-show drink — happy hour lasts until 6 p.m.
• Find out what makes them laugh by catching a show at Comedy Off Broadway. Feeling confident? Take them to an open mic night on the first Tuesday of the month to show off your skills.
• If music is more your thing, choose from one of our 14 live music venues depending on the vibe you’re looking for.

If the way to their heart is through their stomach

• Wow your special someone with a reservation at the picturesque and delicious Dudley’s on Short or with the creative menu + elevated vibe of Lockbox.
• If food is just one part of your date night, start things off with a happy hour at Harvey’s, Carson’s, and nearly 30 others. We recommend drinks at Harvey’s followed by a Lockbox dinner across the street.
• Cooking is a labor of love, so let Pasta Garage + La Bonne Vie help you and your partner level up your kitchen skills. Now, you can play with your food and eat it too.

If you love the great outdoors

• Soak in the fresh air + relax in the hidden urban oasis of Kentucky Native Cafe. You can also dine al fresco at one of these 18 patios.
• The ultimate outdoor adventure awaits with a hike at the Red River Gorge + a slice of pizza from Miguel’s. Then, give your muscles a break and extend your stay at one of the unique spots from The Hive at High Rock.
• If you’re looking for a more lowkey option, you can’t go wrong with a quaint picnic in one of our parks; pick up two grab-and-go $12 charcuterie “bite boards” from Fable for the perfect picnic.
• Wine country meets horse country. Taste + toast to the good times and good wine at these vineyards in Central Kentucky.

For the ones who like to play games (just not with your heart)

• Visit classic video game haven The Burl Arcade for all your old school faves. Pro tip: Pinball is free on Tuesdays + you can commemorate your date with a visit to the photo booth.
• Skip the electronics and opt for a low-key (or high stakes, you decide) board game session at table top gaming spots like Chaotic Good and Villainous.
• Test your aim at Battle Axes. This entertainment center also boasts bowling, high-speed go-karts, and ziplines so you can really show off your competitive spirit.
• Create your own candle or reed diffuser with a custom-blended scent at Wick & Mortar Craft + Candle Cocktail Bar. Or, try painting your own pottery and create special keepsake at The Pottery Place.

If you’re really hoping that it works out

• Heat things up in a different kind of kitchen. Whether you want to bond with a new shared hobby or meet fellow players, we’ll see you on the pickleball court.
• Take your love to new heights by braving the boulders at LEF Climbing Gym. Stop by the nearby Fizzy Fox Soda Shop to rehydrate and chat after climbing.
• Put on your dancing shoes and get ready for some salsa, swing, jazz, or hip-hop classes with Arthur Murray Dance Studio or The Salsa Center.
• Create connection + practice mindfulness through a yoga class or a guided meditation at Shambhala Meditation Center.
• You’ll be the eagle of your date’s eye when you show off your swing at Lexington’s links.

If you want an “old fashioned”-style date

• Two straws, one milkshake — get that, and many more shareable desserts, at Freshie’s Ice Cream & Soda Fountain. Pro tip: Dating a vegan? This spot has options.
• The old school vibes from the Burgers and Shakes on New Circle will take you back in time. If its walk-up window + classic flavored milkshakes don’t bring you back in time, the prices sure might.
• Take a leisurely stroll along South Ashland Avenue to soak in the historic homes, then wrap up the evening with a cozy drink at Charlie Brown’s or Chevy Chase Inn.
• Sip on an actual Old Fashioned at OBC — one of our favorite spots to get the cocktail — or learn more about bourbon in a guided tour of the Pepper Distillery.

If you wanna show off by knowing all the hottest events in town

• Shameless plug: Sign up for our daily newsletter, where we call out our top picks of things to do around town. Your date doesn’t have to know we’re behind it, you can take all the credit.
• Stay up-to-date on the coolest local events around Lexington with our events page (and check out this guide for our tips on navigating the page).