City Cast Madison logo

What To Do for Valentine’s Day if You Hate Valentine’s Day

Posted on February 11
Rob Thomas

Rob Thomas

A woman in an angel costume and a man in a suit of armor

Sure, go see “Romeo + Juliet” on Valentine’s Day. I’m sure that has a happy ending, right? (WUD FILM)


When I was in fifth grade and kids in class were sending valentines to each other, I was thrilled to receive a valentine from the girl I had a crush on. On the outside was a picture of Snoopy holding a sign that said “Be My Valentine.”

On the inside of the card, the girl had written “SNOOPY IS SAYING THAT, NOT ME.”

Which is to say I’ve always felt some ambivalence towards Valentine’s Day. Sure I love chocolates, flowers, and heart-shaped pizzas, but it can be a holiday that comes with a lot of complicated emotions and expectations, whether you’re in a relationship or not.

On the City Cast Madison podcast today, executive producer Hayley Sperling and host Bianca Martin went to two local bars to talk to Madisonians about the state of the city’s singles scene.

If you’re opting out of Valentine’s Day this year, or against the entire notion of a holiday devoted to romantic love, Madison has got some fun ways to celebrate anti-Valentine’s Day. Because heartbreak feels good in a place like Madison.

Crucible, Feb. 13

Madison comedians perform and are then interviewed about their sex lives – the good, the bad, and the ugly. No question is off limits!

Henry Vilas Zoo, Feb. 13 and 14

If you’re feeling all hot and bothered, chill out in some frigid waters in the annual plunge, a fundraiser for Special Olympics Wisconsin.

The Forward Club, Feb. 14

Everybody loves a great dating war story. Cheshire Cat Comedy has put together this showcase of top Madison comedians sharing their favorite dating disasters (and, to be fair, the occasional date that actually went well).

North Street Cabaret, Feb. 14

Drown your sorrows in an ice-cold martini and enjoy tunes from this Madison collective featuring vocalist Anna Purnell and pianist Adam St. Reiff playing classic songs of love gone wrong.

Garver Feed Mill, Feb. 14

If you’ve got your emotional armor on these days, this could be the event for you. Watch armored combat between WiscMCC and the Milwaukee Iron Stags engaging in medieval combat in full metal armor.

Union South Marquee Theatre, Feb. 14

Sure, you might think Baz Luhrmann’s take on the Shakespeare classic is one of the greatest love stories of all time. But do you remember how it ends? If nothing else, this 1996 film is a throwback to a time when it was age-appropriate for Leonardo DiCaprio to date a 24 year old.

The Rigby, Feb. 16

What’s the best breakup song? “Love Hurts”? “Since U Been Gone”? “Someone Like You”? Grab the mic and get it off your chest at The Rigby’s Monday night karaoke.

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 BestSeptember 23

‘Park People’ Will Satirize Madison’s Protest Culture

Madison filmmaker Corey Holl launches a crowdfunding campaign for his new political satire, "The Park People." Explore the proof-of-conce...

Two production staff members on the left hold equipment and a microphone for two actors sitting on a park bench being filmed.
Madison's BestSeptember 8

Ann Garvin Has a Surprise in Store For Her Readers

Madison author Ann Garvin shares her glee in throwing readers a curveball with her poignant, messy new novel, hitting stores September 8.

Author Ann Garvin poses in front of a red wall.
Madison's BestSeptember 1

What To Do in Madison in September 2026

Discover the best things to do in Madison, Wisconsin, in September 2026! From vibrant fall festivals to concerts and athletic events, pla...

A post for the theater show "Steady as She Goes" by Erica Berman. An illustration of a woman with blue flowing hair that looks like ocean waves.
Madison's BestAugust 17

Madison Artist Knocks It Out of the Park With Brewers Mural

Madison artist Emily Balsley unveils her new "Seventh Inning Stretch" mural at Fitchburg’s McKee Farms Park, inspired by her Brewers T-sh...

A woman paints a mural on a wall. The mural has a cornflower blue background and is populated with people and animals in Brewers uniforms and caps..
Madison's BestAugust 6

The Best Fish Fries in Madison

Friday fish fries are a tradition in Wisconsin, and Madison has lots of options. Here are some of our favorites, including Dexter’s Pub,...

A plate of fried fish and french fries.
Madison's BestJuly 31

Madison’s Best: Your Guide To August 2026 in Madison

Discover the best events, festivals, and activities in Madison this August 2026. Don't miss out on the ultimate summer highlights—plan yo...

The City Cast Madison team stands in front of a pop-up tent at the 2025 Magic Pride Festival.
Madison's BestJuly 17

An AC/DC Fan’s Guide to Madison

Get all the details for the AC/DC Power Up Tour at Camp Randall Stadium in Madison! Discover how to get tickets, show times, and where to...

Brian Johnson of AC/DC stands on stage with his arms extended out the side during a concert in Sao Paulo, Brazil
Madison's BestJuly 7

A Phish Head’s Survival Guide to Madison

Are you going to see Phish in Madison at the Kohl Center this week? Here’s what to know, from your chance to score last-minute tickets to...

A crowd of people wearing colorful t-shirts and bracelets smile at a Phish concert.

The latest in Madison

Food & DrinkSeptember 24

The Best New Restaurants in Madison

This month’s list of the area’s best new restaurants includes a new outpost for a wildly popular local pizza chain, a new sushi spot near...

People eating at booths in a restaurant with a glassed-in kitchen at the rear.
Madison, ExplainedSeptember 22

Know the Constitutional Amendments On Your Fall Ballot

Wisconsin's Nov. 3 election features key governor and legislative races—plus three Republican-backed constitutional amendments. Learn wha...

Multiple red, white, and blue "I Voted" stickers are scattered on a white table.
Madison, ExplainedSeptember 21

Big Changes Planned For Madison’s Breese Stevens Field

As Breese Stevens enters its second century, its owners plan to increase the number of concerts and events. But some neighbors of the fie...

A band playing on an outdoor stage in front of an audience.
Madison, ExplainedSeptember 15

The House on the Rock Is Even Weirder Than You Think

Located about an hour west of Madison, The House on the Rock is one of Wisconsin's most infamous, and certainly oddest, tourist attractio...

People in a narrow room covered in glass.
Madison, ExplainedSeptember 15

How To Guard Against Ticks in Wisconsin This Fall

Tick season isn't over yet. Learn what to expect from fall tick activity in Dane County and get expert tips on how to protect yourself an...

A close-up photo of a small eight-legged insect on a human arm.
Madison NewsSeptember 14

How the Historic Meta Settlement Will Impact Wisconsin

Get the details on Wisconsin’s $200M share of the historic $17B Meta settlement as Attorney General Josh Kaul joins City Cast Madison to...

Wisconsin Attorney General Josh Kaul stands at a podium
Food & DrinkSeptember 10

How the Essen Haus Has Avoided the Wrecking Ball...So Far

Celebrate Oktoberfest 2026 at Madison's iconic Essen Haus on Saturday, Sept. 12! Enjoy a full day of live indoor/outdoor music, German be...

The front of The Essen Haus - a grey building with gold trim. The restaurant sign is pink.
Madison NewsSeptember 9

How the U.S.-Canada Trade War Could Hurt Wisconsin Farmers

Canada has retaliated with $20 billion in tariffs against the U.S. following a breakdown in trade talks. Here is how these new trade barr...

a brown cow looks out through a holding pen.