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.

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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:

Most men do not want to hear about a woman’s past relationships. Men don’t need, nor do they want, to be reminded that they were not your first conquest. Discussing every past relationship you had with your present mate is counterproductive and could potentially damage your relationship.

This, however, is a different case. My philosophy is that nothing beats honesty! Explaining to your boyfriend that the gentleman the two of you have befriended was once a lover of yours should not bruise his ego too much — especially if it was a lifetime ago. That is also assuming that you are dating a strong man who is confident and comfortable in his own skin.

Even if your boyfriend is angered or embarrassed at first, he will eventually come to his senses and realize that it is your love, trust and devotion that led you to bare your soul and be honest with him. In my opinion, this can only solidify the relationship and make your bond stronger. If you choose the other path, you run the risk of your former flame admitting the truth to his girlfriend or, worse, to your boyfriend. Then you are caught and might be viewed as being sneaky, which is never a good thing and can possibly destroy the relationship you have been building.

If you truly love someone, then you need to be honest! No, that does not mean that you need to bring out all the skeletons in your closet — just the ones that could affect your relationship. Believe me, in the end he will love and respect you more for being honest than for trying to spare his feelings.

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

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