Tim Gunn on His Last Great Love Affair

The only real relationship I've ever had ended badly after nine years. The hurt I felt after the divorce was the most painful experience I've ever had. My biggest mistake was telling myself I'd never fall in love again—and all the decisions I made when I finally did start a new relationship 10 years later.

In 1992 I was working for Parsons School of Design as associate dean. I was the liaison to our campuses abroad, and I flew to Asia once a month for eight years. I met a flight attendant named Daniel, and I became very fond of him. On one of the flights, there was a baby broker coming back from Korea, bringing back babies who had been adopted in the United States. He didn't have enough handlers, and I was sitting in an exit row, and I thought, I'll hold a baby. This was a bonding experience for me and Daniel. When I left the plane, he asked if he could call me. I said yes.

We dated for about a month. It was long enough for me to know how easy it was, how wonderful it felt, that he was the person I was meant to meet. I could feel from him it was the same way. For me, the thought of merging two households had always been enough for me not to want a relationship, because I'm very meticulous about my apartment and my decoration. But since Daniel was a flight attendant, he had no stuff. It was all perfect.

I gleefully told one of my dear friends—I'll call him Frank—about Daniel one day, and he went nuts. He was very controlling. He went into a diatribe about what kind of cliché this was for a designer to date a flight attendant. He thought it was such a gay stereotype. It became apparent I had to choose. I was either choosing Frank, which was no romance but a strong friendship, or Daniel, with whom I could potentially spend the rest of my life. I chose Frank. I had a tearful, anguished goodbye with Daniel.

I had all these characteristics you have when you're in love or smitten. You think the whole world is rosy. Nothing can go wrong. And then—pow! You're smacked across the face. I know I hurt Daniel. I know I hurt myself. And I ended up developing an enormous anger toward Frank, and that anger ended our friendship. I should have mitigated the situation with Frank and kept Daniel. This is still something I think about with a good deal of frequency. The irony is I ended up with no one.

Interview by Ramin Setoodeh