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Kids, this is the story of how I met your mother, and it was all thanks to 608today.
Okay, 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). Whether you’ve met “the one” or are hoping to impress someone new, we’ve got plenty of local date night ideas that are legen — wait for it — dary.
A night out on the town
- Tickets are on sale for upcoming Forward Madison FC games. Catch a game before heading to the Robina Courtyard for dinner and drinks. Then, enjoy a night of friendly competition at the Aftershock Arcade.
- Take a free tour of the State Capitol and chat about what you learned over chips and queso at Canteen. Round it all off with an early evening show at the Overture Center. With everything in such close proximity, you can spend less time finding parking and more time flirting. Don’t want the date to end? Check out Tornado Room’s late-night menu.
- Heading out to Willy Street? Start with dinner at the Weary Traveler, and grab a drink at Crystal Corner before catching a show at Cafe CODA.

Some friendly competition could make or break your date. | Photo via Turnkey
The way to the heart is through the stomach
- Mint Mark serves up small plates that are great for sharing. This makes for an engaging meal full of food-centric conversation starters and even better meal starters — try the biscuits.
- Impress your date with a meal at one of New York Times’ top 50 restaurants in America: Harvey House. Customize the experience by indicating on your reservation whether you’d like to sit at the bar, in the main dining room, or in the more private upstairs dining area.
- If you like Settle Down Tavern, you’ll love its elevated sister restaurant Turn KeySupper Club. The Thursday date night special costs $60 and includes a salad, two entrees, dessert, and a bottle of wine.
- Lallande offers a cozily romantic ambiance and a seasonal menu that is sure to impress self-proclaimed foodies.
Play games (just not with your heart)
- As home to one of the state’s largest collections of pinball machines in addition to over 150 arcade games, NerdHaven is excellent for double dates.
- You don’t have to be a golf pro to have fun at Blind Shot Social Club. Reserve a golf simulator to play mini-games, or sit at the bar and try your luck at the indoor putting green.
- If your date likes bubble tea, board games, or craft beer Roll Play is the place to be. This casual board game cafe serves up Asian-inspired handhelds and hosts a variety of themed trivia and game nights.
- Figure out how well your partner can defend you from a zombie attack by getting an axe in their hands at Madison Axe. Just fingers crossed the night goes well, because... well, they have an axe in their hands.
If you’re really hoping that it works out
- This 13-mile trip at Lake Loop gives you plenty of time to chat with your date and enjoy the local scenery. Pro tip: Take a pit stop at the Olbrich Biergarten or Monona Bait and Ice Cream Shop for a mid-ride pick-me-up.
- Madisonians are no strangers to the art of pickleball. If all goes well, you and your boo can join a local pickleball league to ensure some recurring date nights.
- What better way to practice trust in your budding romance than by relying on your other half to spot you as you traverse the rock-climbing wall at Boulders? Be sure to get an orientation session if anyone in your party is a newbie.
During the warmer months
- Think: Picnic Point, but less busy. This 3/4-mile paved hiking path at Governors Island offers a view of the isthmus from the north shore of Lake Mendota.
- Rent a tandem kayak at Marshall Boats this summer and paddle into the sunset with your date. If you really want to get cheesy, opt for the swan paddle boat over at Wingra Boats.
- While strolling the Allen Centennial Garden tucked away on the north side of campus, you’ll forget you’re just minutes away from the heart of downtown. Love can still bloom in the winter months, but you’ll have to head over to Olbrich’s indoor conservatory to see living flora.
If you want an “old fashioned”-style date
- It doesn’t get more old fashioned than drinking an old fashioned at The Old Fashioned.
- Transport yourself to the 1950s at the Monty’s Blue Plate Diner known for its ample vegan options and stellar dessert menu. Order one milkshake with two straws to have your own “No Strings Attached” moment.
- Mini-golf is as classic of a date as they come. Cold outside? No worries, you can choose from the indoor or outdoor course at Vitense Golfland.
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 Madison with our events page (and check out this guide for our tips on navigating the page).