Ask Amy: Long-ago love wants to visit ill friend

Dear Amy: Twenty years ago, “Sadie” and I divorced after 12 years of marriage and two children.

Sadie developed a cocaine habit, which destroyed our finances and threw us into debt. She also had a string of affairs and then divorced me.

After the divorce, while I was in shock, “Deana,” a coworker, asked me out. Deana and I had an affair that lasted for several months.

Although she was a wonderful woman, and I was falling for her, I was not ready. I broke it off and left the company for another job.

After five years taking care of my children, I 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 Deana and me after my divorce, I have always retained – but have not acted on – my admiration and affection for her.

I would like to fly out 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?

– K

Dear K: If you think it would be inappropriate to get on a plane to visit this long-ago inamorata, then carefully examine your motives, and decide not to do it.

“Deana’s” illness has not robbed her of her memories or relationships. Aside from your recent contact, you don’t seem to have maintained a friendship with her.

Years ago, after she pursued you and you two engaged in a relationship, you broke up with her and left.

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.

Dear Amy: I have a teenage son, “Theo,” from a previous marriage. Theo lived primarily with me and my second wife, “Margaret.”

Theo and I had an extraordinarily strong relationship.

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 it’s time to confront him about his choice to move back in with his mother, because I think the real reason he moved in with her is that life is just easier for him without guidelines.

What do you think?

– Sad Dad

Dear Sad Dad: 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 should pursue grief counseling, which will help you to express and work through your sadness and anger.

Most teens over a certain age (depending on where you live) are legally allowed to choose which parent they want to live with. You should review your custody agreement.

However, in my view, you should NOT attempt to legally force your son to return to your home, unless living with his mother presents threats to his health or safety.

You don’t offer any details about your wife’s recent passing, and I’m assuming that this was a fairly traumatic time for both of you. Now you are both behaving in a way designed to avoid dealing directly with your grief – or each other – in order to shield your wounded hearts from your vastly altered reality.

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.

Dear Amy: I appreciated your advice to “Cheerful Giver,” whose “love language” is giving material gifts, but was disappointed that on her birthday, her friends and family members didn’t reciprocate.

Thank you for pointing out that calls, texts, and cards represent caring relationships, and that these are gifts, too!

– Grateful

Dear Grateful: As I pointed out, “Words of Affirmation” is another love language. She should become fluent.