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Dear Breakup Girl,

My boss and I frequently communicated with instant messages while using the Internet at night and one night we ended up talking suggestively and ended up having cyber-sex. It was great and a few weeks later, he made an advance towards me at work and I willingly encouraged it more. After about a month, he decided that he couldn't handle it and said he wanted to end things....then he changed his mind again and wanted it again. I was so attracted to him that when he ended it I was devastated so when he wanted it again, I was willing. Now he has changed his mind again, I'm devasted again. We have never actually had sex...just messed around a lot. I'm 41 and he is 63.....I know that he is attracted to me and gets aroused but I think that he is afraid that he will not be able to perform to my expectations and that is the reason he keeps ending it. I have never felt so aroused before in my life than when he touches me....I want to pursue this with him but he keeps backing away. Any advice from you as to how I can talk to him would be welcome.

-- Cindy

Dear Cindy,

I'm sorry, but I could have sworn you said this guy was your boss. Never mind his "performance;" I'm worried about yours. As in, the job kind. Look, I understand the whole vacation-day-makes-the-heart-grow-fonder vibe going on here, and maybe you're experiencing a very real forty-something "Now where will I find someone?" loneliness ("Oh! Right here under my desk!"). But this erstwhile relationship breaks all of BG's rules for worthwhile office romance, including the meta-rule that you must really understand in the first place that it's taking place in the workplace. So. Especially because he is backing away, then so too must you. Men may seem harder and harder to find as the decades go by, but so do jobs. And firing someone, I promise you, is way easier than dumping them. So please please please take some time to do a performance review with yourself: what's missing from your work, your after-work, your future, such that this pursuit would seem like an excellent idea? Then pursue that.

Love,
Breakup Girl

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