Ask Amy: Widow Seeks Dating Advice

By Amy Dickinson | August 19th, 2020

To dump the baggage, or not to dump the baggage – that is the question


Widow with another man who broke her paper heart

Dear Amy: I am a widow and have started dating again.

I am currently seeing a man who gets up early to go online. He is always complimenting women online, even telling them that he loves them.

He and I dated before, and I walked away because of his online activities.

Then he got back in touch, saying that he missed me. He asked if we could try again. During the time we were broken up, he went on a couple of dates with another woman. He promised that she would be gone! Nope. He still keeps her number and has her on his Facebook account.

I am not on his Facebook account, and his page still says that he is single, even though he tells me that we are in a relationship.

I have told him I will not be second to a computer and a bunch of single women.

Amy, I got married at 18 and was married for 32 years when my husband passed away. I don’t know what to do at this point. Should I walk away? I have told him that I do not think it is right to keep old baggage hanging around because it doesn’t give us a chance to move forward as a couple.

I have had a lot of other men interested in taking me out, but I have turned them down because I don’t believe in playing these games.

Please help. I’m thinking of just being alone!

— Worried Widow

Dear Worried: You say you don’t think it is right to keep old baggage around.

Has it occurred to you that in this scenario, you might be the baggage that he is keeping around?

You had a very long marriage, followed by a huge loss. Surely during your marriage, you learned that you are important. You should be the most important person in your world, certainly much more important than a skeevy guy who can yank you back into his orbit just by asking.

Please don’t “move forward as a couple” with this dude. He is showing you exactly who he is. You need to believe him.

You don’t want to play games, so stop playing this one. If you walk away from this person, you will (without question) be the winner.


Want to get even more life tips from Amy? Read more of her advice columns here!


In the tradition of the great personal advice columnists, Chicago Tribune’s Amy Dickinson is a plainspoken straight shooter who relates to readers of all ages. She answers personal questions by addressing issues from both her head and her heart. A solid reporter, Dickinson researches her topics to provide readers with informed opinions and answers. Ask Amy, P.O. Box 194, Freeville, NY 13068

© 2020 by Amy Dickinson

More from Boomer