Dear Amy: My (much older) brother-in-law, "Walter," is a healthy, attractive man in his early 70s who has never settled down.
He 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, and he wasn't proposing fast enough.
Next week, Walter 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. Meanwhile, mutual friends have suggested that she still is interested in him.
Walter asked me if he should lay it all out: 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?
Amy says: My instinct is that "Walter" is getting desperate, or at least, he is sounding desperate. 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 needs 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 Walter discerns her wants and needs — rather than leading with his own — she might be responsive to rekindling their relationship.
Sympathize without intruding
Dear Amy: As we emerge from the pandemic and socialize more, I'm wondering how to handle a certain situation. I have a few acquaintances — "friends of friends" — who have suffered loss because of COVID, drug abuse or other life events. What can I say to these people at festive affairs, knowing they've suffered?
Amy says: At festive affairs, grieving people sometimes try to take a break from the burden of processing their losses. You should acknowledge these losses, and then give them an opportunity to expand on their situation, or thank you and move on to another subject.
For people who have survived challenges or other tragedies (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 without their permission, your choice to bring it up would create problems in their friendship.
Send Ask Amy questions via e-mail to Amy Dickinson at askamy@tribpub.com.
