A Single’s Guide to Dating in Milwaukee, WI

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.

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.

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:

ComedySportz

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.

CSZ Milwaukee, 420 S. 1st Street, Milwaukee, WI, USA, +1 414 272 8888

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.

Holler House, 2024 W. Lincoln Avenue, Milwaukee, WI, USA, +1 414 647 9284

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.

Walker’s Point Kitchen, Shop & Pairing Bar, 211 S. 2nd Street, Milwaukee, WI, USA, +1 414 223 0123

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.