City Cast Madison logo

Treat Yourself to the Best Solo Dates in Madison

Posted on February 11, 2025   |   Updated on September 30, 2025
Rob Thomas

Rob Thomas

A woman sitting alone at a table in a restaurant.

Sometimes a meal on your own can be a great date night. (Westend61/ Getty Images)

No date? No problem. While Valentine’s Day is typically thought of as a time for couples, it’s essential to love and appreciate yourself first before trying to connect with another person. Here are some ideas for solo dating in Madison, for Valentine’s Day and any time you want to show your favorite person a little affection.

🧘Take a Meditation Class

Meditation can be a great practice to be present in your body and pay attention to how you’re feeling. Listen to the City Cast Madison podcast today as host Bianca Martin talks to Buddhist monk Khenchen Konchog Gylatsen Rinpoche about the benefits of the meditation practices he hosts through the Wil-Mar Center and the importance of self-love and community care.

City Cast

A Madison Buddhist Monk's Guide To Self-love & Compassion

00:00:00

💆 Get a Massage

Now that you’ve gotten your mind right with meditation, treat your body with a massage. Indulge Spa, Kneaded Relief, and A Healer’s Hand are three locally-owned options that will take good care of you.

🚶 Take a Nature Walk

Sure, it’s a little chilly out there, but if you’re bundled up and the sun is shining, a Wisconsin nature walk can be invigorating as well as beautiful. Stroll through the Arboretum (and maybe search for the Lost City), or take a walk out to Picnic Point and gaze out on frozen Lake Mendota.

📚 Browse an Indie Bookstore

A great way to spend an afternoon is looking for your next great read at an indie bookstore in Madison, like Lake City Books, A Room of One’s Own, and Leopold’s Book Bar Caffe. As the name implies, you can also get coffee or a cocktail at Leopold’s while you browse.

🍜 Have a Great Solo Dinner Out

It might feel a little awkward going out to dinner by yourself, but trust me – everybody’s focusing on their own thing and nobody cares that you’re all alone. My advice is to eat at the bar at a nice place like the Tornado Room, Merchant or Nattspil, and bring that new book you got at the indie bookstore for company. Also, just like you wouldn’t want to be constantly on your phone on a date with another person, put it away and enjoy being out on your own.

🍿Take Yourself to a Movie

There is nothing like seeing a movie on your own – you don’t have to negotiate with somebody else about what to see, and you don’t have to share your popcorn. If you’re in a romantic frame of mind, AMC Fitchburg is showing a restored version of 1990’s “Ghost” starting on Valentine’s Day, and Marcus Palace is showing, “Let the Sparks Fly,” an all-day marathon of Nicholas Sparks movies (including, you guessed it, “The Notebook”) on Saturday.

On Valentine’s Day, Union South Marquee Theater is hosting a double feature of two somewhat unusual love stories, “Lisa Frankenstein” and “Portrait of a Lady of Fire.” And it’s free!

Share article

Hey Madison

Sign up for your free daily toolkit to get the most of the city you love.

Can't subscribe? Turn off your ad blocker and try again.

Madison's Best

See All
Madison's BestJune 10

How to Celebrate Pride Month 2026 in Madison

The city’s biggest LGBTQ+ gathering, OutReach Magic Pride Festival, isn’t actually until August, but there are still plenty of ways to ce...

A group of 6 people sit on a bench smiling, looking on at the Middleton Pride Festival
Madison's BestJune 3

Your Guide to Frank Lloyd Wright's Madison

Legendary designer Frank Lloyd Wright called Madison home and he left his mark on the city. Here's some of his most famous buildings, fro...

A building with glass windows and a triangular roof.
Madison's BestJune 2

Your Guide to June 2026 in Madison

If you’re looking for a page-turner to take to the beach this summer, UW-Madison graduate Joseph Eckert is coming back to town to Lake Ci...

A group of people at tables in front of a marble building.
Madison's BestJune 1

How Madison’s Capital City Theatre is Reinventing ‘RENT’

Madison's Capital City Theatre is putting on a bold new version of the Tony-winning musical 'RENT' at the Orpheum Theater June 5-7. For i...

A woman gestures to several other people in a room.
Madison's BestMay 12

Wisconsin Authors Are an Open Book on New Podcast

On the new podcast "Writing Forward," Madison writer Jeff Oloizia interviews Wisconsin authors about their writing process, how to be suc...

A man in a blue shirt stands next to a shelf of books.
Madison's BestApril 30

Your Guide to May 2026 in Madison

From Brat Fest to Tulip Fest, from 'Newsies' to Charlie Berens, there's lots going on in Madison this spring.

A man in a gray shirt in front of a blue brick wall.
Madison's BestApril 29

The Madison Mystery Tour Is Coming To Take You Away

Over a half-century after they broke up, the Beatles still have a huge hold on popular culture. For over a decade, the Madison Mystery To...

A man in a bow tie plays an electric guitar behind a man playing a keyboard.
Madison's BestApril 27

Madison’s Circus Scene isn’t Clowning Around

While Circus World in Baraboo is what put Wisconsin's circus scene on the map, there's lots of acrobatics, clowning and more going on in...

A man and a woman in a circus ring juggling hoops.