Ask Amy: Reuniting couple need relationship rehash – The Denver Post

Dear Amy: My (much older) brother-in-law, “Walter,” is a healthy, attractive, heterosexual man in his early 70s who is comfortable financially, but has never settled down.

He’s had girlfriends throughout his life, but he never found someone he thought was “The One.”

Walt is now realizing and regretting his past emotional insecurities and fear of commitment. He doesn’t want to be alone for the rest of his life.

His most recent girlfriend left him abruptly (without explanation) after a couple of months of dating.

I think it’s because she was looking for a “green card ‘Sugar Daddy,’” and he wasn’t proposing fast enough.

He discovered that she was playing the field, looking for a husband. He was pretty devastated.

Next week Walt is going to be in his hometown to see family, and he invited a former lady friend, “Barb,” to lunch with the intention to see if they still have chemistry.

They dated years ago, but he called it off.

He now thinks he was being too narrow-minded. Barb is a lovely person and will be retiring soon. I’m surprised she’s still single.

Mutual friends of his and Barb’s have suggested that she is still interested in him.

Walt asked me if he should lay it all out on the table: He wants a companion to enjoy life with for their golden years.

I thought that might sound insulting to her, as if he couldn’t find anyone else and so he’s circling back to her.

What do you think?

– Younger SIL

Dear Younger: My instinct is that “Walter” is getting desperate, or at least, he is sounding desperate.

If his ex was “playing the field, looking for a husband,” isn’t he now “playing the field, looking for a wife?”

His goal should not be to seal the deal with this first lunch, but to get to a second date.

I suggest that he start by offering to do a little “relationship rehash” with her, in case there are any lingering issues he may need to explain or apologize for regarding their previous relationship and how it ended. He should focus on listening to her during this initial meeting.

If Barb is a woman of substance who has been single for a long time, she has already been to the puppet show and seen the strings.

If Walter listens to his date and discerns her wants and needs – rather than leading with his own – she might be responsive to rekindling their relationship.

Dear Amy: As we emerge from this dense fog of isolation caused by the pandemic and socialize more, I’m wondering how to handle a certain situation.

I have a few acquaintances who are “friends of friends,” who have suffered immeasurable loss during this year due to COVID, drug abuse, or other life events.

What can I say to these people at festive affairs, knowing they’ve suffered so much?

– Speechless

Dear Speechless: At festive affairs, grieving people may sometimes try to take a break from the daily burden of processing their losses. However, you should acknowledge these losses, and then give them an opportunity to have a conversation with you and expand on their situation, or thank you and move on to another subject.

For someone who has lost a loved-one: “Janet, I was so sorry to learn that your mother passed away this year. I can only imagine what this has been like for you.”

For people who have survived challenges or other tragedies involving family members (and their situation is well-known to you), you can say, “I understand it has been a rough year. I hope you’re doing OK.”

You should not convey that you are aware of intensely private family matters if you are unsure about the source of your information. If your mutual friend passed along private knowledge about another family’s struggle without their tacit permission, your choice to bring it up would create problems in their friendship.

Dear Amy: I am a 71-year-old male living in Southern California.

I have been called “Sweetie, Honey, and Dear” at various stages of my life by female service providers of all ages and backgrounds.

Admittedly, I don’t get called by these harmless endearments in a professional setting or in the healthcare arena, but I don’t take offense and certainly do not register “disgust.”

Could it be that women of a certain age are the ones feeling disrespected, while guys just roll with it?

– Tim

Dear Tim: Your theory is possible, except that this topic was originally raised by a group of men.

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

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