Ask Amy: Is it too late to visit old flame?

Dear Amy: Twenty years ago, “Sadie” and I divorced after 12 years of marriage and two children. Sadie developed a cocaine habit, which threw us into debt. She also had a string of affairs and then divorced me.

After the divorce, “Deana,” a coworker, asked me out. Our relationship lasted for several months. Although she was a wonderful woman, I was not ready. I broke it off and left for another job. I eventually remarried. Deana married at about the same time. Her husband is a terrific man who adores her.

Now I hear that Deana, who lives in another state, is in an assisted-care facility with MS and in declining health. Although the timing was not right for us after my divorce, I have retained my admiration and affection for her.

I would like to see Deana before she passes, but I think it would be inappropriate to do so. I sent a holiday card to her and her husband, expressing my sympathy for her illness. Should I leave it at that?

Amy says: If you think it would be inappropriate to go visit this long-ago inamorata, carefully examine your motives, and then decide not to do it.

Aside from your recent contact, you don’t seem to have maintained a friendship with her. My point is that she might not have lingering fond memories of you and might not want to see you. And feeling sorry for her or closing the circle on your own unresolved feelings for her would not be the best reason to connect now.

Before hopping on a plane, you should at the very least contact her and ask if she would like for you to visit.

Margaret passed away three months ago. Then Theo moved back in with his biological mother without much of an explanation. Everyone tells me that he’s grieving and that I need to give him time. I think I should confront him about moving back in with his mother, because I think the real reason he moved in with her is that life is easier for him without guidelines.

What do you think?

Amy says: Because you are stung by two momentous losses, I think you should take the issue of Theo living with you off the table for now and focus instead on ways to maintain a positive and compassionate relationship with him during this period of extreme change and instability.

You also should pursue grief counseling, which will help you to express and work through your sadness and anger.

Be patient. Reach out with kindness and concern. Offer Theo options to see you on weekends if he would like, and do your very best to be his loving dad, even from a distance.