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Attendees mingle at a singles mixer event held by 207 Connect at Ocean Gateway on Jan. 31, 2026. There were two sessions that day, the first for singles over 40 and the second for people in their 20s and 30s. (Brianna Soukup/Staff Photographer)

PORTLAND — After Robin Traub’s relationship ended a couple of years ago, she decided not to rejoin dating apps right away and instead took time to focus on herself. She went back to school, moved to Falmouth and changed jobs.

When her friend texted her a photo of a sign for a singles mixer she’d spotted while walking, Traub agreed to go, thinking it might be a good way to put herself out there again. At 40 years old, she wasn’t sure whether she’d have better luck at the session for 20- and 30-somethings or the session for everyone older. She signed up for both.

“The apps are more like an interesting waiting game,” she said. “You meet somebody upfront, and you already have the whole intonation, the vibe.”

Efficiency was a common reason given by people at one of those mixers, at Ocean Gateway in Portland last month, for trying an in-person dating event. On dating apps, conversations with matches can often drag on for a long time only to fizzle out or, worse, give an impression of someone who’s not who they say they are. When they do result in a date, people said, you can tell very quickly whether there’s any attraction — and if you’re about to waste even more of your time and money over coffee or dinner.

Attendees mingle at a singles mixer event held by 207 Connect at Ocean Gateway. (Brianna Soukup/Staff Photographer)

On the flip side, you might dismiss someone on an app because your interests or hobbies don’t align, but you’d click if you’d met in person, said a woman in her 40s at the mixer who came from New Hampshire with a friend.

Whether it’s older singles tired of seeing the same faces or younger people who view the apps as uncool, a desire for alternatives to online dating is fueling an uptick in singles events in town, with Valentine’s Day providing an extra boost.

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Gritty McDuff’s held a speed dating event for 30- to 40-year-olds last month. “Date My Friend” at Ocotillo, where people were invited to pitch their pals to other singles this week, sold out. A group called Sick of Swiping is holding its first event, “Cuties & Cocktails,” at Apero in Biddeford on Feb. 25. The next night, there’s a board game speed dating event for people in their 20s and 30s at Cowbell in Westbrook.

GETTING PRACTICE

Although any stigma of meeting online is long gone, people still say they’d prefer to find a match through friends or a chance encounter. That’s harder than ever, though, with remote work and delivery services keeping people inside their homes, a decline in drinking taking bars out of the equation for many, and reverberations of the #MeToo movement leading to more apprehension about approaching strangers.

Steven Chettleburgh, 25, thought he was doing everything right when he moved to Maine for a job two years ago. He went to events through Meetup groups and eventually started his own, a group for people in their 20s interested in activities like hikes and trivia nights.

“I really thought, I’m going to meet someone romantically through one of these things,” Chettleburgh said. He ended up only making friends.

Event organizer Steven Chettleburgh talks to the crowd at a singles mixer held by 207 Connect at Ocean Gateway on Jan. 31. (Brianna Soukup/Staff Photographer)

That’s why he started 207 Connect, the host of the Ocean Gateway mixer, which sold more than 400 tickets between the two sessions. Called Single and Ready to Mingle, it was the second round of events he organized, and he plans to continue holding them every four months or so.

Even for those who don’t meet anyone they want to date, Chettleburgh said, attending the events can give people practice talking to potential partners and a chance to build their confidence. Getting three matches at the first event helped him feel more comfortable approaching women, he said, and Chettleburgh ended up meeting someone at a bar on Wharf Street who he’s now been dating for a few months.

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His events mix the technology of dating apps with the authenticity of meeting in person by having attendees (who paid $30-$50, depending on when they bought tickets) fill out a questionnaire that matches them with other people in the room, easing their way into initial conversations. There are still some snags, however: A picture of one woman’s match only showed the prospective partner’s midsection; another woman got matched with herself.

DIFFERENT FORMATS

The two sessions had very different feels, Robin Traub said. The session for people 40 and older, which was held in the afternoon and comprised mostly women, was more subdued, like a networking event. The younger crowd was more aggressive about pursuing matches during their evening session, which had a party vibe and equal gender split. (The events are open to all gender identities and sexual orientations, but Chettleburgh said almost everyone who has signed up has been straight.)

Robin Traub at a singles mixer event held by 207 Connect at Ocean Gateway on Jan. 31. Right at the age cutoff for the two sessions, she decided to attend both. (Brianna Soukup/Staff Photographer)

Traub said she ended up hearing from a couple of men the next day, but no one she was interested in dating. Still, she’d do an in-person event again, she said, preferably with a more structured format, like speed dating.

Those are the types of events Caity Fiero, 38, has been holding through The Bug Club, which she launched after going through a breakup in 2023 and hearing so much negativity about dating apps.

She thought there had “to be a place for single people to be together in person,” she said.

Fiero, who also helped promote the Portland mixer, said she’d read that the best dates involve a “third object.” So, at her first event, attendees met beside different works on the wall of the Portland Museum of Art. Others since have incorporated goats, karaoke, arcade games, foraging, volunteering and oyster shucking. They’ve ranged in size from 20 to 40 people, and everyone meets each other.

“Even if they’re making friends,” she said, “it just feels good to get out of the house.”

One of the repeat attendees eventually asked Fiero out. Now, they live together, and she’s hoping to find someone to take over the events, which she believes “are best run by other singles.”

Based on her and Chettleburgh’s experiences, taking up the mantle might also be the best way to find a match.

Leslie Bridgers is a columnist for the Portland Press Herald, writing about Maine culture, customs and the things we notice and wonder about in our everyday lives. Originally from Connecticut, Leslie came...

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