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After an amicable divorce two years ago, JL Knapschaefer was ready to get back into Pittsburgh’s dating scene.

Knapschaefer, 38, had been with her husband for more than a decade, so dating had changed a bit since the last time she was looking for love. But, eager to meet people, she started going out regularly, and joined the most popular dating apps.

“My very first time online dating, I started talking to this guy who was an investment banker, and he seemed very intelligent,” she says.

The two started texting, casually getting to know each other before making plans to meet in person.

“One night, he texted, ‘I just want to be transparent with you and tell you that I have a lot of baggage,’” she says. “And he tells me that the reason that he got a divorce was because his ex-wife actually had him committed to a psychiatric hospital. He told me the whole story — how his ex-wife packed up their apartment and moved to another city while he was committed, never to be seen again.”

Knapschaefer could feel the burgeoning relationship fizzle. “It was just a lot to process,” she says. “And a little too much.

The next night, Knapschaefer had a date scheduled with another guy she had matched with, and they started chatting about dating horror stories.

“I said, I don’t have any horror stories yet, but I do have this crazy story from last night,” She says. “I told him the story, and he immediately goes, ‘Oh my God, does he work at [REDACTED]? And is his ex-wife
[REDACTED]?’ It turns out that this guy that I went on a date with, the last woman he ever dated was the ex-wife.”

“And that,” says Knapschaefer, “is Pittsburgh dating. The scene is so, so small. You’re only a few degrees separated from everybody else. It’s insane.”

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Meeting Offline

Navigating everything from dating apps to online groups (like the private Are We Dating the Same Guy: Pittsburgh Facebook group, which has more than 40,000 female members, posting warnings and red flags about potential dates) can be enough to make a modern dater want to give up.

Add in a small citywide dating pool, and after a few weeks on Hinge, Tinder or Bumble, it can feel like you’ve already seen everyone who’s available.

Related: Remembering ‘Date Night TV’

Just ask Lauren Mims, 31, who has lived in Pittsburgh since 2021. She started dating last year, after she and her husband divorced. Having previously lived (and dated) in bigger cities like Denver and Dallas, navigating Pittsburgh’s scene has been an adjustment.

“I was at brunch for my birthday, and my waiter recognized me, apparently from an app,” Mims says. “He kept staring at [me] and at the end, he said, ‘Oh, I figured out where I knew you from. You haven’t responded to me on Hinge yet.’ And I was like, ‘Oh gosh, this is super awkward.’

“That’s not the move right there. If you don’t match with someone, you probably shouldn’t pester them in public.”

It hasn’t all been dreary though for Mims, who says she’s not looking for anything serious at the moment. “I have had so much fun this year,” she says. “I’ve had some really great dates, and I’ve had some flings that I just knew weren’t going to have long-term relationship legs, but they were still really great guys.”

But it’s not always easy, especially in the years since the pandemic with the rise in remote work (goodbye office romances) and changes in social behaviors.

“For me, the hardest part is just discovering where to go to meet other single people,” says Dan Bednarczyk, 28, a software engineer who lives in the South Hills. “I work from home, and I live a little more in the suburbs, so I just don’t organically get that interaction with other people in my day-to-day life. I try to put myself out there in places intentionally, but I’m just not finding a lot of success with that.”

There are big concerns about invading someone’s personal space, he says, or coming off as too needy or creepy.

“When I was younger and single and dating, I found that more men came up to you in public,” says Lisa Black, a 54-year-old single from Westmoreland County. “They would start a conversation with you. But I’ve found that now, when I go out with my girlfriends, or when I’m out doing things by myself, I’ve noticed that men don’t approach women anymore.”

And while a recent survey by WalletHub found that Pittsburgh is the 18th best city for singles in the country, ranking particularly high in the ‘dating opportunities’ category, which notes a high share of single gender balance, in practice, meeting people face-to-face is rough.

“I have asked out a couple of people I’ve encountered in just my day-to-day life and have received some very polite rejections from people who are already in a relationship,” Bednarczyk says. “I’m also very cautious about the culture that women experience. I’m trying not to be pushy or anything like that. I just want to give it as much space and make sure that there’s mutual interest before pursuing anything.”

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Where Are the Singles? 

For Matt Borrelli, 32, meeting people isn’t the problem — meeting single people is the issue.

“I tried for like six months or so. I went to speed dating. I went to in-person singles events. I got involved with a running club to get to know people,” he says. “It’s not hard for me to go up and talk to people, but usually the majority of people that I meet are already in a relationship or married.”

So, for most Pittsburgh daters, it’s back to the apps.

Black, who is recently divorced after a 25-year marriage, started to dip her toe back into the dating pool last year. Using dating apps has been a totally new experience for her.

She has created her own code to follow when she’s on the apps, based on her experience: No separated men, no one who says they’re an “entrepreneur,” and a hard pass if there’s nothing but pictures in his profile (“You can’t fill out the prompt or write a bio? If you can’t take five minutes to type something up about yourself, how are you going to be able to carry a conversation?”)

Right now, she’s looking for a serious, long-term relationship, but is finding it hard to find someone who doesn’t want just a … singular situation.

“If they put in, ‘looking for a fun woman,’ or ‘looking for women to have fun with,’ you know what that is,” she says. “That’s code for, ‘I just want to get laid.’ Which is fine! But when I see that, I’m done. I’m not swiping on that one.”

At first, she says, using dating apps felt like a safe way to get to know a lot of people, before meeting them in person. But she’s had a few instances that went from innocuous to scary quickly.

“There was one guy I had been chatting with, and he asked if I wanted to meet up for a drink. I said yes, and he asked for my address and said he would come over. So, I said, ‘No, I don’t know you, I’m not having you over to my house,’” Black says. “And he immediately went on a tirade and told me that if he ever saw me on the street, he would kick my teeth in. Like, holy cow! I dodged a bullet right there.”

Now, Black goes straight for a background check on Google and other searches whenever she has a full name. “All my friends who are dating do it.”

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The Matchmaker

If you want to bypass all the swiping and the heavy lifting of looking into every potential partner yourself, there is another option: The matchmaker.

For 31 years, Susan Dunhoff has been making matches for Pittsburgh singles through her company, The Modern Matchmaker. She says that with an 85% success rate (long-term relationships and marriages), the connections that she makes are lasting.

“What we do is very, very personalized,” Dunhoff says. “We get to know our clients very well.”

Dunhoff’s clients, she says, are selective people who don’t want to spend their own time looking at profiles online or in bars trying to meet other singles.

“They just want quality matches,” she says. “Some have tried the internet. They don’t want that. They don’t want to look at thousands of people with a lot of fake profiles.”

Dunhoff charges thousands of dollars for her service, which involves an in-depth meeting with clients to understand everything that makes them them: Their lifestyle, their goals, their dreams, and their plans for the future.

She’s seen a lot of changes in both the way that people date in the last three decades and the quality of partner that someone looks for — and, there have been a lot of changes in the years since the pandemic began.

“People have become even more selective than usual,” she says. “It’s like, if I’m going to spend my time with someone, it really better be worthwhile, and that’s much more heightened than before. We tell our clients to be selectively open-minded, because we don’t want them to miss meeting the love of their life.”

The key to finding the right person, Dunhoff says, is to be honest. Be honest with yourself about what you want, and be honest about who you are to any potential partner.

Borrelli, who primarily finds dates on Hinge, Tinder and Bumble, agrees that being upfront is the best way to weed through people who have hang-ups about certain life choices. As a Ph.D. candidate, he’s making plans to move out of the city in the next year. It’s one of the first things he lists on his dating profiles.

“Right now, I’m being really, really aggressive with putting out that I’m looking for a life partner,” he says. “I say that I’m going to leave Pittsburgh eventually. I say that I don’t have a car. I’m putting these common deal breakers right up front, that way people know. I want to be intentional about it and upfront about who I really am.”

Mims, still happily dating her way through the apps, says that being open minded has been the key to her having good experiences.

“My advice is just to be honest about what you’re looking for, short-term, long-term, whatever,” she says. “If you just want to have fun, be honest about it. There’s no reason not to.”