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Wednesday, October 05, 2022
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This weekend is Tu B’Av, and it got me thinking about my own dating life. And I remembered: everything about dating my now-husband, Caleb, was wrong.

I had just experienced a devastating heartbreak, and a close friend suggested I head to a Chanukah party with her to get me out of the house. I reluctantly agreed. The party was an eclectic group of 20- and 30-somethings, and I found myself sitting on the kitchen counter, chatting with several people. Across from me was a man who was very inquisitive, listening to me intently as I spoke, but not saying all that much. At the end of the party, he offered to walk me home.

Caleb made his first move by asking me to Shabbat dinner at his apartment, with other friends of course, which I attended. Shortly after, he began texting with me, trying to find ways to take me out on a formal date. The problem was, I was completely uninterested.

Not only was I recovering from my last relationship, but I had also discovered that Caleb was a decade older than me—a detail I wasn’t sure he knew either. On top of that, my roommate had divulged that Caleb had received semicha from Yeshiva University (with a memorable, “Channa, he’s a rabbi!”) and I took this to mean he might be too frum for me. I made up my mind that Caleb was not someone I envisioned marrying, but it didn’t stop him from trying to get me to go out with him.

A few months later, I was home visiting my parents for Pesach. In recounting my dating woes with my younger brother, he said to me: “Channa, what do you have to lose?” He had a point. When I returned to New York, I finally agreed to a date with Caleb. And, as they say, the rest is history. When everything seemed wrong, it turns out, it was right.

This is exactly the sentiment that my friend, Michelle Siegel, expressed to me when we spoke about dating. Michelle is a shadchan for YUConnects, an online dating platform for singles who affiliate in one way or another with YU. In her short time as a shadchan, Michelle has made several successful matches and counting.

“I try to encourage everyone I work with to just give it a shot,” she shared. “You never know what you might be missing. Especially when you haven’t met in person yet.”

My conversation with Michelle was driven by the fact that although I may have had a “meet-cute” story with my husband—a serendipitous introduction worthy of a rom-com—most Orthodox 20-somethings are introduced to their spouses through either a shadchan or an online dating platform (or both). I wanted the perspective of someone working on the ground, and someone who really understands what it’s like to be a 20-something in the dating world.

“Most people expect to see an older yente-type when they meet the shadchan, and they’re surprised when it’s me.” Michelle continued that she sees her age as an advantage, since it makes her all the more relatable to the singles she works with. “I have so many single friends, and I feel that I’m more in tune with what they want. Plus, there’s a benefit in having a network of people I know that I can set up.”

Michelle and her husband, Moshe, are committed to setting up their 20-something friends on their own time, hosting meals with only singles in the community and constantly brainstorming which couples might be compatible. Michelle explained that she joined YUConnects as a shadchan to expand her personal network of singles, especially because she has so much fun with matchmaking. “It’s really satisfying to know that I’m helping create Jewish homes,” she told me. “I just love learning about people and making connections for them.”

So what’s Michelle’s advice for all the singles out there reading this column?

The same thing my brother told me: don’t knock it till you try it. “A lot of people are really hesitant when they see something on a dating profile or shidduch resume that they think might not be for them. Of course, everyone is entitled to their red flags, but I say if it’s a ‘maybe,’ then make it a yes.”

Needless to say I wish I had a Michelle in my life back when I first met Caleb—because once I got to know him, it became an immediate yes.

*Michelle Siegel, LCSW, lives in Washington Heights with her husband, Moshe, who she also met at a Shabbat dinner. When not setting her friends up, she works as a social worker with the elderly and volunteers as a matchmaker for YUConnects. If you’d like to connect with Michelle, she can be reached at [email protected]*


Digital editor Channa Fischer is the token 20-something in the office. She lives in Washington Heights.

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