Essay: A Year of Mediocre Dates in Milwaukee

What it’s like to move to Milwaukee and start dating

This Story is Part of MilMag‘s February Love & Sex Feature

Name: Libby, 25

Height: 5’4″

Location: East Town

Alcohol? Sometimes.

I’m Catholic, an editorial designer. I went to Ohio University. The key to my heart is pizza and beer. 

THAT, IN A NUTSHELL, is my Hinge dating profile along with six pictures of myself. Hinge is a dating app that is “designed to be deleted,” focusing on relationships rather than one-night stands. 

When I moved to Milwaukee at the start of 2019, I saw dating as the best way to explore the city through familiar eyes. I went to more bars and ate more cheese curds than I would have alone, and even the bad dates were better than any I had in my previous two years living in a retirement community in Central Florida, a decidedly low bar.  

I clicked through my standards in the app: men ages 25-32, living within 25 miles, open to all religions and ethnicities. Most dates took me to the East Side. I awkwardly pushed through the quiet, shy guy at Up-Down MKE. I watched a Bucks game at The Garage with the guy who returned a call from his grandma mid-date. At Black Husky, I politely smiled across the table from the one who told me how his ex just dumped him and left him with a puppy. These were the better dates.

The lesser dates included the guy who lectured me on the appropriate amount of alcohol to drink when out with a stranger, and the guy who talked so much that one of the only sentences I got out was, “You’re a talker, huh?” 

And the guys who didn’t even make it to the dating round were about equal to the one who asked for a full-body picture because the last girl he met “lied about her weight.” We hate that guy.

The dates came in waves. I would have one or two a week until I felt hopeless and deleted the app. A couple of dates turned into short-term flings, and at their demise, I re-downloaded it. Amid my last fling with a 26-year-old designer came a new job opportunity in New York City. The spark with the guy was so mild that I didn’t think twice about taking the job. 

Looking back on my year of mediocre dates, my best advice is to tell your date you are new to town; he will ALWAYS order the cheese curds.


This story is part of Milwaukee Magazine‘s February issue

Find the issue on newsstands or buy a copy at milwaukeemag.com/shop.

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