Why Does Everyone Treat Being Single Like A Problem?

The desk was made by her grandfather. Her father said he had been planning to refinish it for her wedding, but added: “I don’t know how much longer we would want to wait, and I also wouldn’t want to go to the trouble otherwise.” The listener, a 37-year-old artist living in New York, left the room and cried. When she told her father she felt hurt that marriage seemed to be the only achievement worth celebrating, he apologized and they never spoke of it again. Months later, she was still thinking about it. On this episode of Oversharing, co-hosts Jordana Abraham and Dr. Naomi Bernstein unpack that exchange alongside two other listener dilemmas about the social pressure on single people — a pressure that, they argue, is often reinforced by the very people who love them most.

The Desk, the Wedding, and the Achievement Hierarchy

Bernstein validated the listener’s hurt — she rated it a seven out of ten — but she also saw a deeper dynamic at work. The father’s comment, she said, was a “pylon” for an insecurity the listener already carried: that she was behind her younger brothers, both married in their thirties, and that her own timeline wasn’t working out. The desk comment hit because it confirmed an internal fear. “It would be great to feel like it wasn’t also an insecurity of yours,” Bernstein said.