Bintel Brief: Shoshanna Rikon Says Not All Skeletons Should Be Left in the Closet

Dear Shoshanna,

My boyfriend rarely asks me anything about past affairs, which is fine by me. But I’m wondering if I’m obliged to divulge some facts nonetheless.

The problem is that one of our best couple friends includes a man with whom I had a brief affair several years ago — well before I met my boyfriend. This other friend and I remain close, but I’m no longer interested in him sexually or romantically in the least, and so I hesitate to tell my boyfriend about it. I don’t want the friendship made awkward by the past and, more importantly, I don’t want to hurt my boyfriend needlessly. I get the impression that the girlfriend of my old fling also knows nothing of our affair.

Should I tell my boyfriend about my history with this friend? Or is it better to keep quiet about it?

MUM’S THE WORD?

Shoshanna Rikon replies:

Shoshanna Rikon is the founder of Shoshanna’s Matches, which serves Jewish singles in the New York tri-state area.


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Bintel Brief: Shoshanna Rikon Says Not All Skeletons Should Be Left in the Closet

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