Chicago’s breakout star of ‘Jewish Matchmaking’ to share his songs

Stuart Chaseman may be the perfect man.

“What I bring to a relationship is: I’m very handsome, I’m very intelligent, I have a ton of charisma. But by far my greatest quality is my humility,” the 53-year-old Wicker Park resident says when we first meet him on the Netflix show “Jewish Matchmaking,” the first season of which aired last year.

But don’t take Chaseman’s word for it.

Thousands of people on TikTok, Reddit and other social media platforms apparently agree that the shortish, slightly jowly man with a nasally voice that brings to mind the late comedian Gilbert Gottfried would be a catch.

One Chaseman TikTok video drew 24 million views.

It might have something to do with his deadpan delivery.

“Within 100 feet of a Jewish event or a synagogue, I’m like Tom Hanks-level famous,” he said during a recent sit-down in his condo.

Almost a year after he appeared on the show (No, he didn’t find a match: “I’m still on the prowl.”), he’s still milking his unlikely fame.

Netflix

Chaseman, a singer-songwriter, is set to perform with his band, the Born Again Sinners, Friday at Hey Nonny in Arlington Heights. On tap: songs from the new album “Secrets, Lies and Alibis,” as well as other original music and some covers too. He also plans to do a meet-and-greet after the show, answering questions about his appearance on “Jewish Matchmaking.”

“Ironically, it focuses a lot on failed relationships ...,” Chaseman said of the album, which was released in 2023. “There’s a lot of grieving in the record, a lot of coming to terms with the universe’s plan for me, (which) was different from what my plan was and I just have to go with the flow.”

He runs an advertising company, but has always hungered for a music career.

“You’re talking to someone who has managed to make hundreds of dollars in the music industry ...,” he says. “But I’ve never really supported myself with music.”

Another part of his plan was not being 50-something and single, which is how he came to apply online for the Netflix show. The application process involved proving his Jewish heritage, he said.

“They took it really seriously,” Chaseman said. “I took pictures of my parents’ graves, where you could see the Jewish stars. That wasn’t good enough.”

He also had to sign up for Ancestry.com, he said.

While he’s talking, the phone rings.

“I’m in an interview right now,” he politely tells the caller. “I have a publicist and I’m not looking for another one.”

He didn’t really hit it off with either of his two dates on the show, but he certainly made an impression with viewers, who found his rough-around-the-edges look, humor and vulnerability refreshing.

Netflix

With one date, Chaseman, an only child, shares how he lost both of his parents recently and never expected to be quite so alone in the world.

On the same date, he tells the woman, who is 4-foot-6, “I cannot stand movies with Hobbits.”

“You were being so honest and vulnerable. I’d try to set you up with my aunt if I thought you wanted to date someone older than you. Then you could be part of my large, loving, and loud Jewish family!” says one Reddit user of Chaseman’s appearance on the show.

Chaseman gets a lot of that even now, he says — people trying to set him up with their daughter, their mother.

He isn’t totally alone, though. He has plenty of friends and his two dogs, Bailey and Rosalita, to keep him company.

“I’m interested in entering the last relationship of my life, and that hasn’t happened yet,” he says.

In the meantime, he keeps dating.

Of a recent date, he says: “She kept talking to her cat just like it was a person. I thought, this chick is crazy. So as soon as I got home, I told my dogs about it and we all laughed.”