Ask Amy: Widower worries about dating again

Dear Amy: I am a 73-year-old man. My wife died three years ago. This year would have been our 50th year of marriage.

Although we had many ups and downs throughout our marriage, we loved each other and raised two wonderful children who now have children of their own. (I also have a daughter from a previous marriage.)

I have many grandchildren and great-grandchildren.

I love and live for my family. I don't know what I would have done without them after my wife’s death.

Over 40 years ago my wife caught me kissing “Doreen,” my friend’s wife, while we were at a party. Nothing more ever happened. My wife never really got over the betrayal, but we agreed to stay together and work on our marriage. We also stayed friends with Doreen and her husband. He died 25 years ago.

Through the years Doreen and I have stayed friends through email, Facebook, phone calls, kids’ birthday parties, etc. My children know her and have always been friendly toward her.

Doreen and I have spoken on the phone many times in the years after my wife’s death (the "kiss" has never been mentioned). I’ve become interested in dating her.

I mentioned her to my son recently and he was very adamant that he did not want me to date her. He said his sister(s) agreed with him.

I don’t even know if Doreen would go out with me, but am I wrong to want her to be a part of my life? I'm afraid my kids will turn away from me. I think my wife told them about this long-ago kiss.

I was totally surprised by my son’s reaction.

What should I do?

– Just Friends

Dear Friends: When you essentially ask someone for permission to live your life within completely respectable boundaries, you take a risk that they will say, “No.”

And – reporting my own non-scientific findings and insight, I’d say that around 70 percent of adult children say a quick “no” to the prospect of their older parent dating after a loss. (They often come around later.)

Just as you don’t have the power to run your kids’ lives, you should not give them the power to run yours.

So, don’t ask.

For now, the only asking on your part should be confined to “Doreen.” Furthermore, I hope you won’t make the mistake of believing that you need to explain or apologize for a regrettable choice you made 40 years ago, which you and your wife dealt with as well as you could.

My overall point is that your health and happiness should be the most important thing to the people who love you. Handle this new relationship discreetly and in thoughtful stages.

Dear Amy: In January I loaned my granddaughter $9,000.

She agreed to pay me back when her bank opened the following Monday. I know she had the money because her father (my son) was involved in a lawsuit and she received a large sum of money.

It has been several months now, and she has not paid me yet.

I am considering suing her because I am retired and living on a fixed income. What should I do?

It pains me that I am being treated this way after I was so kind to loan her this money.

– Stiffed

Dear Stiffed: Some of the details you offer don’t quite hold together.

If your granddaughter could have paid you back from money in her own account on a Monday, then why did she need this money so urgently before that?

Did she tell you why she needed this large sum, or why her father didn’t loan it to her?

I hope you have some documentation regarding this loan.

Start by asking her – in writing — to repay you.

You could also try asking her father to repay you.

If you don’t receive satisfactory answers (and your money), then – yes — depending on where you live, you could take this to small claims court, which would be an easier (and less expensive) process for you.

I hope you charge her interest.

Dear Amy: Ah, I sighed when I read your response to “A Friend” about a broken friendship: “True friends are daffodils in the snow, and they are well worth freezing for.”

I’m currently experiencing a friendship that is dying on the vine; this helped me to put it in perspective.

– Moving On

Dear Moving On: This analogy was inspired by venturing into a snowstorm to rescue some wounded daffodils.

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(You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.)