To tell, or not to tell...

Dear Mistress,

I have been with my boyfriend for several years, and we're incredibly happy. My boyfriend works at a small company, and he's in charge of training new hires. Well, the guy they just hired happens to be the guy I lost my virginity to in college. My boyfriend will be working with him, one on one, for the next month.

We all went to the same college, so I think my boyfriend knows I at least dated this guy, and I may have even told him about losing my virginity to him — but, honest to God, I can't remember.

The company holiday party is next week, and we'll all be there! I am freaking out. Should I remind my boyfriend that I once dated him? What if he then asks about the extent of our relationship? I just want to make the proper and mature decision, so I don't hurt my boyfriend's feelings.

Signed,
Cherry

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Dear Cherry,

Don't freak out. Think this through logically: Most couples, at one time or another, swap stories about losing their virginity. Either you have already told him your story and don't remember, or it will come up at some point in the future. And, now that this guy has reappeared in your life, you must acknowledge it. Remain calm. As with any touchy situation, if you treat this like a big deal, you're more likely to get a dramatic response from your guy.

Don't waste any more time before the holiday party. Ask how your guy's day at work was, and then ask him if he remembers that you and his new trainee dated in college. From there, I would let him guide the conversation. If he wants more details, he'll ask. If he doesn't care to know the extent of your sexual relationship, don't force it on him.

Some people might say you shouldn't tell your boyfriend, but remember — if you don't have a relationship built on trust and honesty, what do you really have?

Honestly,
MM