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 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.
Madison's BestJuly 1

Your Guide To July 2026 in Madison

Plan your perfect July in Madison with our ultimate guide. Discover top summer events like Fete de Marquette, Maxwell Street Days, and At...

A large group of people sit at tables on a terrace overlooking the beach.
Madison's BestJune 16

How To Celebrate Juneteenth 2026 in Madison

June 19 is Juneteenth, the day that America celebrates the end of slavery. But there are events all week in Madison to commemorate the ho...

A group of people walk down the street on a sunny day in a parade celebrating Juneteenth. People in the front hold a banner that reads "June 19, 1865."
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.

The latest in Madison

Food & DrinkAugust 13

These Madison Restaurants Are Gone But Not Forgotten

We also asked our readers and listeners to share their favorite defunct Madison restaurants, and dozens of you responded. Here are some o...

A strip mall restaurant with a green-and-white sign.
Madison NewsAugust 10

Listen to Our Interviews with Wisconsin’s Candidates for Governor

There are still seven candidates in the running for Wisconsin governor. Find out where they stand on the issues.

Four voting stations sit empty in front of a windows on a sunny day
Madison, ExplainedAugust 10

Meet the Madison Democrats Running For Assembly District 76

Find information about the candidates running for Wisconsin's Assembly District 76 seat in the upcoming primary election.

Five political candidates sit on a stage with microphones in front of them.
Madison, ExplainedAugust 10

Your Guide to the August Primary Election in Wisconsin

Get ready for the Wisconsin election on August 11. Learn where to vote in Madison, what ID to bring, how to vote early, and mail-in ballo...

A white sign with a United States flag image and the words “VOTE HERE VOTE AQUI” stands upright in front of a Madison municipal building.
Madison NewsAugust 5

Madison Police Clear Ruiz Memorial and Encampment Site

Madison authorities dismantle the Corey Ruiz encampment at Baldwin & Williamson. District 6 Ald. Davy Mayer discusses the fallout on City...

Candles and flowers form a makeshift memorial.
Madison, ExplainedAugust 3

How State Government Is Reducing Its Footprint in Madison

Wisconsin is shrinking its downtown Madison office space. Learn how the long-term Vision 2030 plan will change the state government's phy...

A gray multi-story building in downtown Madison.
Food & DrinkJuly 30

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...

Two people standing at a counter at a pizza restaurant.
Madison NewsJuly 29

Site of Corey Ruiz Shooting Becomes a Living Memorial

Protesters close Madison blocks for a Corey Ruiz memorial site, sparking debate over safety and traffic. Chief Patterson shares no new up...

A sprawling makeshift memorial for Corey Ruiz with flowers and candles.