Old School Jewish Matchmakers offer timeless perspective on dating

The dating scene for seniors isn’t always as glowing as it’s portrayed on reality TV. Between the catfishers and the two-timers, one older dater described her prospects as less “Golden Bachelor” and more “like panning for gold in a sewer.” Knowing how seniors can struggle to connect online, friends Freddie Weisberg and Char Cohodes launched Old School Jewish Matchmaking, a pro-bono dating service for Minnesota Jewish singles 65-plus.

Supported by the nonprofit news and networking group TC Jewfolk, the duo has been handpicking pairings since Valentine’s Day. They share what they’ve learned about senior daters’ desires and dealbreakers. And why matchmaking is not for the faint of heart.

This interview has been edited for length and clarity.

Q: How did you get the idea to do matchmaking for seniors?

FW: After my mom passed away, within a pretty short time, my father’s brother fixed him up with a blind date, who became the second love of his life. I thought about how wonderful it was that he met this person. And I don’t know how he would have met anyone otherwise, because we wouldn’t have had him doing online dating. He had an AOL mail account, so that tells you something right there.

Q: You’re building on a long tradition in the Jewish community, sticking with an approach that relies on intuition vs. algorithms.

CC: This is the last generation that won’t have complete computer literacy, that won’t completely understand how to connect electronically.

Q: And you personally vet potential partners.

FW: We meet everyone in person. And it’s the chemistry of meeting someone, and both of us looking at each other and saying, “Wait a minute. That person could probably go with this person.”

CC: It’s a gut thing. The true matchmaker had the gut.

FW: In about 10 or 15 minutes, we already know someone in common. We’re not doing official background checks, but our background check is basically the community.

CC: 10 minutes is generous. I’d say it happens in closer to 4.

Q: In light of the loneliness epidemic, I’d think there’s value for daters simply in having you listen to their story.

FW: It’s like they were waiting to be able to come in and talk about it. They’re giving us their life story, and they’ve had a love relationship, and somehow have lost that relationship, whether by divorce or death. And depending on what they had, they’re embracing the possibility of another chance at that.

CC: You can almost see a spring in their step as they leave the interview. It’s like they have set something in motion. They leave a little taller and that for us is reward right there.

Q: You sought advice from Bobbie Goldfarb, who founded Jewish Dating Service in the 1980s and helped many young singles start families. How is your cohort different?

FW: We ask, “Do you drive? Do you drive at night?” Because this is important.

CC: You’re not gonna tell an 80-year-old man to tuck his shirt in. If he isn’t going to tuck his shirt in by now, he isn’t going to tuck his shirt. So we’ve got to find somebody who doesn’t care that the shirt isn’t tucked.

Q: What are older daters’ dealbreakers? Do they have lower standards?

CC: They’re like, “I really I don’t think I could handle a smoker or a heavy drinker.” But they are really willing to tolerate a lot for this.

Q: What are daters looking for?

FW: Some are looking for romance and love and a starry night. But there’s also people who are looking for companionship and for someone to go out to dinner with or go see a play.

Q: What determines a pairing?

FW: The word I like to use is the tone of the person, their gestalt. Maybe they’re intellectual and they like highbrow things and like to go deep in a subject. Where someone else might be lighter, they’re more carefree. It’s kind of like their pulse.

Q: Sounds complex.

FW: It’s not for the faint of heart. There’s so many nuances. We’re not making matches just to make matches and send people out on dates. We want to be saying: This will be successful.

CC: And if one of our guts is saying, “I don’t think so,” we don’t fix them up.

Q: So after you decide on a match, you each call one party and make sure they’re not cousins or haven’t already dated.

CC: That has happened.

Q: What happens after you give them the other person’s information?

FW: We very intentionally say, “Do not create a whole conversation in text.” Now they can google, and some are even googling them while we’re talking to them on the phone. They’re like, “Oh, yeah, I see him.” But I had done some online dating at one point, and this writing back-and-forth thing, you create this whole persona. It’s ridiculous. Writing is very different from talking and meeting in person, and you’d have this whole long thing created, and by the time you met him, it was like, Oh, God, they’re nothing like I thought they were gonna be.

Q: I appreciate how you prevent ghosting by letting one person know if the other doesn’t want to see them again.

FW: It’s hard to break that news. It’s not happy news. But I would say, if you’re thinking about dating again and you’re hesitant, you’ve got nothing to lose, really, by trying. It’s not scary. You have us as backup.

Q: Have you been asked to match younger daters?

FW: We’ve heard from some moms who are trying to fix their children up. We’ve also had some younger people say, “Would you consider a 48-year-old?” And we want to say to the community: Someone else should pick this up for the younger people. The younger people want it, but we’ve got our hands full.