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Date night ideas in Lexington

Got a hot new fling? Hoping to spice things up with your longtime partner? We’re here to help plan your next date in the Horse Capital of the World.

Lexington, Kentucky's skyline with a sunset of blues, reds, and oranges

Lexington’s vibrant nightlife scene is ready to host your picture perfect date night. | Photo by @femibranded

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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 (and saved his kids a lot of time). Regardless, whether you’ve met “the one” or are hoping to impress someone new, we’ve got 19 local date night ideas that are legen — wait for it — dary.

For the ones who want a night out on the town

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 the creative menu + cozy vibe of Cole’s 735 Main.
  • If food is just one part of your date night, start things off with a happy hour at Harvey’s, Carson’s, and 30 others.
  • 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.
A group of men playing pickleball under lighted courts.

It’s not uncommon to see the courts packed at Kirklivington Park. | Photo by Paul Hooper

If you love the great outdoors

  • 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.
  • You’ll be the eagle of your date’s eye when you show off your swing at Lexington’s links.
  • The ultimate outdoor adventure awaits with a hike at the Red River Gorge + slice of pizza from Miguel’s. If you’re looking for a more lowkey option, you can’t go wrong with a quaint picnic in one of our parks.
A man and woman standing in front of a row of pinball machines

Enjoy happy hour specials from 4 p.m. to 6 p.m. while you try your luck free pinball on Tuesdays. | Photo by The Burl Arcade

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

  • There’s nothing like a little friendly competition to strengthen your bond. 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 Chaotic Good or Villainous.
  • Test your aim — and theirs — at Battle Axes. But that’s not all this entertainment center also boasts bowling, high speed go karts, and ziplines so you can really show off your competitive spirit.

If you’re really hoping that it works out

If you want an “old fashioned”-style date

  • The old school vibes from the Burgers and Shakes on New Circle will take you back in time. It’s easy on the wallet — burgers start at $1.23 — and brings back that nostalgic feeling with its walk-up window + classic flavored milkshakes.
  • Two straws, one milkshake — name a sweeter situation. Get that, and many more shareable desserts at Freshie’s Ice Cream & Soda Fountain.
  • Take 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.

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).

What did we miss? If you know a perfect date spot that’s not on the list, guide us in the right direction using this survey.

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