A Single’s Guide to Dating in Milwaukee, WI

Dating in Milwaukee | © VISIT Milwaukee
Dating in Milwaukee | © VISIT Milwaukee
Photo of Victoria Borisch
Freelance Writer14 February 2018

While movies like Love Actually make picking up attractive singles in any Milwaukee bar look super easy, city locals may need to put in a bit more effort to find love in “The Good Land.” Despite some disappointing statistics, not all hope is lost for Wisconsinites seeking romance. Milwaukee is a vibrant, young city full of singles who are ready to mingle, and offers plenty of fun settings for first dates.


Unfortunately, the dating scene in Milwaukee seems pretty grim. According to a recent study, Milwaukee comes in at a disappointing 65th place on the list of best cities for singles in the USA. For those seriously searching for a special someone, it might be worth the commute to Chicago (7th place) or even Madison, which comes in at a respectable 15th place.

Milwaukee | © Jeramey Jannene / Flickr

How to meet

Dating apps are a good place to start for those who aren’t familiar with the singles scene. Bumble and Tinder are popular favorites for Milwaukeeans. However, dating apps can be tiresome and frustrating, so for those wanting a more proactive approach, there are a number of events for singles that take place in Milwaukee, including a variety of singles Meetups, speed dating, and even an occasional singles night at Miller Park. Milwaukee also has a matchmaking service to help out those who are struggling with meeting people in general. For a more casual approach, spend some time people-watching in Milwaukee’s beer gardens in the summer or strike up a conversation with an attractive stranger you bumped into while walking your dog.

Fun date ideas

A great way to find out if you’re compatible or to start off a relationship on the right foot is with a fun first date. Even if the date doesn’t go as you had hoped, at least you will have a memorable time. Check out a few of these unique first-date spots in Milwaukee with your new love interest:


Everyone loves to laugh, so attending a show at ComedySportz is a great way to take the pressure off when dating someone new. Their improv comedy shows are set up as sporting events with a referee and two teams playing against each other. You may even have the opportunity to show off your wit in front of your date by volunteering to join in the game.

Improv Comedy Show | © ComedySportz

Holler House

The Holler House might not look like much from the outside, but on the inside, this tavern is home to the oldest sanctioned bowling alley in the USA. This historic location, which opened in 1908, is considered to be one of the best bars in the country. Be sure to make a reservation in advance though, as two of the lanes are so old that a pinsetter will have to attend to them while you’re playing.

Indulgence Chocolatiers

For those who enjoy the sweeter things in life, Indulgence Chocolatiers offers the unique experience of chocolate pairing classes. Skip dinner and a movie, and instead spend the evening learning which chocolates taste best with different wines, beers, and spirits. These classes take place at Walker’s Point pairing bar, and pre-registration is required. If you aren’t up for a full class, you and your date can simply stop by the pairing bar, and the helpful staff will be happy to give you some recommendations.

Indulgence Chocolatiers | © VISIT Milwaukee

For those who love still eludes, try falling in love with Milwaukee itself! Exploring all that the city has to offer will surely introduce you to new people who share similar interests. Don’t forget that some of the best relationships start through mutual friends.