Chaseman, a Chicago-based musician and marketing professional, is definitely not who we think of when we think of the slick and stylish stars of reality dating shows. He’s in his 50s (a young 52, if you will). He has both studded leather pants and snakeskin pants in his closet, which he jokes are either for a night out or Chabad. And while he jested about being the Jewish Brad Pitt in a Zoom interview with Kveller, I think it’s fair to say that Chaseman isn’t your typical leading man (though Brett Gelman might call him a “jaddy”).
But Stuart shines in comparison to some of the other men on the show — like Ori, who only wants to date blonde women with blue eyes, or David, who still asked Dani to sleep with him after she valiantly sent him packing for being an asshat (I think that’s the technical term).
Chaseman has come out as the unchallenged unproblematic king of “Jewish Matchmaking.” He’s candid, funny, self-deprecating, principled — his partner has to be “totally tolerant of gay marriage, no racial stuff, pro-choice… any degree of intolerance towards the way people live their lives is a deal breaker.”
“I’m 51… but I read at a 56-year-old level,” he jokes to one date. And in what I’d argue is hands down the best date of the show, he makes seasoned comedian and disability advocate Pamela Schuller laugh out loud. Though the two didn’t click romantically, Chaseman is grateful that he found a new dear friend in Pamela who he still texts with.
On TikTok and in Reddit threads, fans of the show try to breakdown the magic and the draw of Stuart Chaseman. Some credit it to his regional accent, his candor and openness. They’ve compared him to Pete Davidson (who he’s somewhat familiar with), Nick Kroll (who he doesn’t know at all) and the Basement Yard Brothers (who neither of us know of, it turns out).
Chaseman has been reading all these threads and happily interacts with his new legion of fans, much to their surprise, and sometimes, their embarrassment (someone once wondered if Chaseman spoke slowly because he was high or dropped on the head as a child, and Chaseman responded with “probably the latter.”) He even joined Cameo.
But one person who wasn’t a fan of the way Stuart Chaseman was portrayed in “Jewish Matchmaking,” at least initially, was Stuart Chaseman himself.
“I mean, to be perfectly honest with you, after the show came out, I was disappointed with the edit,” he tells me, after revealing the show didn’t air any of his meetings with his friends and dating coach.
“I haven’t watched it again, and I don’t think I will,” he professes, “but I’m extremely flattered and extremely appreciative. I couldn’t have expected anything more than what I’ve gotten. And obviously, the edit was fine in that something came across in me that connected with people.”
Talking to Chaseman for almost an hour, I’m even more won over than I was by him in the show, mostly because he’s exactly who he has broadcast himself to be. Most people as funny as him use humor as a shield, a way to stay in shallow emotional waters — but Chaseman is vulnerable and contemplative.
He’s a bit surprised about how fans have reacted when meeting him in real life. He has found himself saying, “You are far too starstruck for my level of fame. Like if you ever met Tom Hanks or something, I’m completely concerned about what would happen to you.”
Still, Chaseman doesn’t believe this is the end of his time in the spotlight, joking, “I’m in maybe minute two of my 15 minutes of fame.” He said he’d love to have his own Netflix show, if the opportunity arose, but “I couldn’t play a role other than Stuart Chaseman.”
Here are some things you may not know know about Stuart Chaseman:
He has two dogs, Rosalita and Bailey, who belonged to his late parents (when I talk to him, he’s a little mad at Bailey, because the dog has bitten him after being a little territorial with food. Chaseman, however, wants us to know that he is “the sweetest, sweetest dog.”)
The marketing company he owns is called Scholastic School Supplies and it sells advertising on school supplies, which are then given away for free to schools around the country. (Stuart tells me he has no recollection of how he got into this particular niche business, but that he loves it.)
His leather pants are still in the normal rotation of his clothes, though his snakeskin pants are not.
His limits for a partner is still two cats and no dogs (he has his hands full with Rosalita and Bailey).
While he grew up in the very Jewish Glenview suburb and Wicker Park neighborhood of Chicago, and currently lives in Wicker Park (where, he tells me, he feels like an old man hanging out at a college party), he’d be willing to move out of the Midwestern city for love.
His Jewish parents, who passed away a few years ago, showed him what love should look like. “There was no denying the fact that the two of them had chemistry, that the two of them found the love of their lives, that they were ride or die,” he tells me. “That they had something that I still have yet to find apparently.”
While he grew up Jewish — “I was bar mitzvah-ed, I went to Hebrew school, I went to Sunday school, we celebrated the Jewish holidays” — he doesn’t really connect with the spiritual part of Judaism, which he made clear in the show.
Yet being Jewish is undeniably part of his life: “My brain is wired a certain way as a result of that, and that’s not going to change.”
While he may not be joining a synagogue any time soon, he is a very active cultural Jew. “I wasn’t really aware of the degree to which I’m culturally Jewish till maybe I was 40 years old,” he says.
He’s obsessed with Chicago’s Manny’s Deli, he hates bagels that are too doughy, and firmly maintains cinnamon raisin bagels don’t go with lox. He loves chive cream cheese and an onion or poppy bagel. He’s mad about the fact that some noodle kugels are made without raisins (he is deeply offended by Katz’s kugel for this reason).
His favorite Jewish show continues to be “Curb Your Enthusiasm,” and has thoughts on “Seinfeld”: “It was like a coded thing — Jews knew it was Jewish humor, but it’s like, ‘Let’s not tell anybody else because we don’t want to exclude them. Don’t tell them this is Jewish humor, and they’re gonna like it. It’s our secret!'”
His favorite Jewish musician is Bob Dylan. Unlike Dylan, he can’t see himself ever converting to a different religion, because he refuses to replace “one book that I don’t believe half of the stuff in” with “a whole new book that I don’t believe half the stuff in.”
His own music is certainly Dylan-esque, filled with angst and contemplation. The two words he uses to describe it are “honesty and vulnerability,” and despite him coming off as quite a jovial guy on the show, his music gets pretty dark. “There’s a particular song, ‘Nights Like These,’ on the new record, and the song lyric says, ‘Nights like these always make me sad / I think about the family that I never had / How I fucked up everything / It’s probably best I ain’t a dad / Nights like these always make me sad.’ I don’t even know if I could have accessed [those feelings] if I wasn’t doing it through songwriting,” Chaseman says.
He contains multitudes. “I’m very flattered, and very appreciative that people think I’m funny. If I brought joy into their life that way, I’m very happy. But that’s not all of me. I’m a poet. I’m a deep thinker. I’m a serious person. Check out that side of me as well. If you only want to see me as the funny guy and that’s the side you like, that’s fine, but at least know there’s more dimensions to me that just making wisecracks.”
And, importantly, Chaseman still believes in love. He has some hopes of being in the second season of “Jewish Matchmaking.”(I’d argue that the fans wouldn’t have it any other way.) “I’m looking to meet my bashert at this point,” he says. “I haven’t given up on love at all.”
Talking to Chaseman, it’s not really clear to me why he’s single, except that, at the end of the day, a kind of alchemical luck is probably the greatest reason why people end up partnered in life.
As someone who has been married for over a decade, I look at my single friends and can’t really explain why I’m married, and why they aren’t. When I tell Chaseman about said friends, he very respectfully asks how old they are. So if you think you may be, or may know someone, for Stuart Chaseman, I’m sure he would love to hear from you.