Death and dating

I saw my boss’ husband on an online dating site. His profile said he is single. My boss was diagnosed with a terminal illness so I’m afraid telling her could make her more sick. I don’t know whether he and my boss have an open marriage but if so, shouldn’t his relationship status reflect that? Otherwise, he is deceiving his wife and potential matches. I consider my boss a friend and want to do the right thing. Please help.

If you were married, facing terminal illness, and your husband was dating online as a single man, would you want to know? Or if a man you met online identified himself as single but was actually married, wouldn’t you like a heads-up? My Magic 8 Ball says, “Without a doubt.” Let’s say your boss does know her husband is dating. Telling her you viewed his profile might inspire him to be more discreet. But if she’s unaware he’s cheating, telling her what you saw allows her to decide how to proceed. Either way, she’s empowered to make a decision.

One caveat: Are you certain you saw your boss’ man, not his doppelganger? I’ve scanned online dating sites and thought I saw men I’ve met before, too. I wasn’t always correct. And, occasionally online dating site staff intentionally post intriguing profiles of people who don’t exist. So before you speak to your boss be certain that, other than relationship status, even the FBI would agree the profile you saw matches your boss’ man.

I’m a 54-year-old man with major depression interested in a younger, very attractive, single mother in my apartment complex. We usually visit standing on the porch outside her apartment, but a few times she invited me in. Once she bent down directly in front of me, giving me a clear view of her breasts. I thought she did this on purpose so I asked her out. She acted put out, asked for my number, said she’d call but never did. Sometimes she mocks me. Another time I dropped by, she and a man were going out with her kids. Would I be foolish to try to progress toward something more with her?

Only visit if you can seduce your mind into making less of the cleavage flash. Your neighbor may be a flirt. Or she might just be moving her body with no idea you’d think cleavage was an invitation to something more. Think of it this way: I like biceps but if the shirt sleeve of a man I was talking to lifted and I saw his well-defined bicep, should I imagine he wanted to date me? Ah, no. Here’s what’s really going on: You’re lonely. So your mind has cobbled moments when you felt a tingle of delight and tried to interpret those moments to fit a desired end game. In this case, that means a date or sex or a relationship. But your neighbor isn’t signaling her attraction. She enjoys chatting with you, nothing more. Let that be enough. Stop your mind from thinking about her. She’s not the one for you.