Kyle Grossmeyer, a 33-year-old actor turned financial planner who returned to his native Milwaukee last year after seven years in Los Angeles, says texting is his least favorite method of communication. And where is texting unavoidable? Dating apps.
Like many 30-somethings, Grossmeyer is no stranger to the apps. He’s experienced many of the challenges you hear about – ghosting, being left “on read” and meeting someone IRL only to quickly realize you don’t have a connection. “There are so many people on the apps that you can just keep swiping,” he adds. “A lot of people get anxious, overwhelmed or have decision paralysis.”
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So, there are plenty of reasons why Pitch-A-Friend Milwaukee is Grossmeyer’s favorite singles event in the city.
Grossmeyer has been pitched once and presented a friend another time. He says Pitch-A-Friend is a great way to meet like-minded folks who are trying to bypass the downsides of dating apps.
“It hits the sweet spot of being fun while people are still looking for something serious,” he says. “Some speed-dating events feel like a five-minute interview … this is more lighthearted.”
Pitch-A-Friend isn’t the only new service dedicated to combatting dating-app fatigue in Milwaukee. UnHinged Speed Dating, founded this October, holds invite-only events at local bars for singles 30 and up. Here’s what to know about both groups.
Pitch-A-Friend hosts singles PowerPoint nights at Milwaukee bars
Pitch-A-Friend’s Milwaukee chapter – one of numerous chapters across the country – was founded in October 2024. The concept is simple: You, a single person, attend one of the twice-monthly events with a trusty friend, family member or co-worker (who doesn’t have to be single), and that person presents a 3-to-5-minute slideshow “pitching” you to a crowd of other love-seekers.
Julia Graybill took over as Pitch-A-Friend Milwaukee’s chapter host in September, meaning she plans, hosts and promotes all of the events. Graybill is a self-described “lover of the grind.” This is her third job in addition to full-time work as an accountant and weekend gigs as a wedding day-of coordinator.
Graybill was eager to grow Pitch-A-Friend’s presence in Milwaukee because she hopes to bring back the “personalized aspect” of dating that she feels has been lost with the apps.
Pitch-A-Friend events kick off with a fun game like “This or That” or “Red Flag, Green Flag.” Then come 6-10 pitch presentations (for $5, you can apply to pitch your friend here). Every three presentations or so, attendees break for intermission, giving aspiring lovebirds a chance to grab drinks, chat or even play another game. At the end of the night, Graybill re-presents the last slide of each presentation, which features the contact info of the eligible singles pitched earlier in the night. It’s your responsibility to reach out to a potential match!
Feeling shy? You don’t have to pitch or be pitched to attend. Graybill estimates between 50 and 70 people attend each event, meaning at least 30 are there just to hang out. The only requirement is that you’re over 21.
“Our normal age range is mid-20s to late 30s. I believe our average age right now is like 33,” Graybill says. “But we do have people that are like 21 or 22 and up to late 40s, early 50s.”
Pitch-A-Friend held its first-ever event at Uncle Buck’s. The Deer District bar has since become the “home base” for many subsequent events, but Pitch-A-Friend has also set up shop in suburban venues like The Hounds on Tap in Menomonee Falls and Wauwatosa’s Lion’s Tail Brewing Company. Graybill has even hosted LGBTQ+ and 40+ events. In the new year, she hopes to expand Pitch-A-Friend’s reach in the suburbs and step up its number of events to at least three per month.
Interested in Pitch-A-Friend? Stay up-to-date at pitch-a-friend.com/milwaukee or on Instagram.
UnHinged brings application-based speed-dating to Milwaukee
Chelsea Freuck, a 36-year-old business owner, was inspired to start UnHinged Speed Dating by her own experiences. While living in New York, she enjoyed the “structure and efficiency” of the classic speed-dating format, but wasn’t meeting people similar to herself.
“I’d been to several speed-dating events that were really closer to singles mixers. There was no guarantee you’d actually get to talk to someone you were interested in and potentially no easy way to exit a conversation you didn’t want to be in,” Freuck recalls. “Most of the events were also 21-plus, and in my mid-30s, my friends and I often felt we were in a completely different stage of life than many of the people attending.”
UnHinged (Freuck admits the name is a play on a certain popular dating app) has hosted three speed-dating events so far at downtown Milwaukee bars, with aspirations to expand to the suburbs.
How does it work? Any single person over 30 is welcome to apply to UnHinged’s Date-A-Base by answering a short list of questions about their dating preferences and uploading a photo. The UnHinged team then hand-selects up to 30 attendees (15 men and 15 women) for each two-hour event.
“We select attendees… based on age range and who we believe might genuinely click,” Freuck explains. “We look for thoughtful, engaging answers about why you’d like to attend, great photos and, just to be safe, we do a quick online check to make sure everyone is real and trustworthy.”
Events begin with a 30-minute check-in period where singles can grab a drink and mingle. Once speed-dating kicks off, women stay seated while men rotate every five minutes. There’s a one-minute break between each speed-date to jot down notes.
At the end of the night, everyone submits a form indicating who they’d like to speak to again, Freuck says. “We review the selections and, the next day, let each attendee know about any matches,” along with their contact details.
At UnHinged’s most recent event, three-quarters of attendees ended up with at least one match, Freuck says. Friendships have also blossomed.
“I’ve even seen Instagram photos of attendees who didn’t know each other before the event hanging out weeks after, and it’s been so rewarding,” Freuck says.
UnHinged currently aims for about one event a month. Three are scheduled for 2026 so far, including a 40+ event on Jan. 8. Stay up-to-date at unhingedspeeddatingmke.com and on Instagram.
