Annie's Mailbox

Ask Amy column

Q. Our single, older, male next-door neighbor has become very chummy with our 19- and 20-year-old boys, who are in college and living less than one hour away.

He often invites them to join him for dinner, movies, and bowling. We used to socialize with him occasionally but don’t anymore.


Our sons think he’s a great and generous guy. We see someone who makes a lot of effort to see our sons often, and we are uncomfortable with it. He’s been fairly close to our family but as he’s been way too generous (at times) with gifts in the past, I’ve asked that we stop exchanging gifts. All the same he sneaks gifts to our sons and tells them not to tell us.

I’ve mentioned boundaries, but it seems to make no difference to him. We don’t want our sons to see us as being negative. They see no boundary issues concerning him.

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This feels just a bit creepy to us.

Parents in a Quandary!

A. If you are creeped out and trying to protect your sons from inappropriate contact, then you shouldn’t worry about seeming “negative.”

I can certainly understand an older individual having young friends. But the red flag is that this neighbor has asked your sons to keep secrets from you. No responsible and respectful adult would ask young people to lie to or deceive others.


You should be completely frank and honest with your sons. In the age of Jerry Sandusky and countless other stories of trusted adults “grooming” and then victimizing young people, if you “err” it should be on the side of transparency and honesty.

You should also tell this neighbor — plainly and clearly — that you do not feel comfortable with his overt focus on your sons. Beyond that, if you have further (and concrete) reason to suspect anything creepy is going on, you should notify the police.

Q. I’m a single woman in my 20s. Six months ago a new employee was hired at my office. I was instantly attracted to him but he was married and so I never acted on my feelings. His wife is a wonderful person and we have socialized together.

Recently he confided that he has been completely preoccupied with me for months. He finds reasons to visit me at work, overanalyzes my text messages (or lack thereof), and says he loves me like he has never loved anyone before (including his wife). He says he regrets marrying his wife because now he is experiencing true love for the first time.

I love him, too, but have told him nothing can happen between us while he’s married. We have had long, intimate conversations but have never been physically intimate.

He has confided that his marriage is ending. I refuse to allow anything to start before then, but I still can’t help but feel like a home wrecker. I so desperately want to be with him but I can only imagine the judgment from co-workers and friends if we end up together. Can I follow my heart or should I cut ties with him entirely?


A. Assuming that you are accurately reporting the details of this relationship, I’d say he — not you — is the home wrecker.

It would be best if you could take a step back — way back — to consider this objectively before taking the relationship further. People leaving their marriages always say they never should have married in the first place. And maybe that’s true. But you should be very careful and skeptical.

Send questions via e-mail to or by mail to Ask Amy, Chicago Tribune, TT500, 435 N. Michigan Ave., Chicago, IL 60611.
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