Sunday, October 12, 2025

Don't Ask, Don't Get

My girlfriend, who is in her early 60s and a longtime divorcee, texted me the other day, saying that she wanted to talk. My first thought was Oh No! because all too often that’s code for Help!

I told her to call, and she did right away, so I assumed something was wrong.  

However, her voice didn’t reflect that. She sounded hyped up, like she just consumed an extra cup of coffee. She then proceeded to say that she had taken a friend of hers – a much older gentleman – to do his errands and, on their way home, out of the blue, he began to reflect on their friendship.

“We have been friends for a long time,” he said…and “I’ve been thinking about this for awhile…if you ever want to cuddle, I’d be happy to do that.”

He went on to say that he is sure she misses the closeness she shared way back with her ex-husband and that he isn’t suggesting they be intimate but rather that he could provide comfort for her.

Maybe he simply expressed what his heart felt. Maybe he was so appreciative for their bond that he wanted to do what he could to soften the loneliness he perceived she felt. Maybe HE missed the cuddling, etc. since his wife passed over a decade ago. Maybe his proposal was a smokescreen for let’s just start here and see what happens. Maybe he was moved by the compassion he felt for his friend at that moment and surprised himself by saying it. Anything was possible.

At the time, she was speechless, as much about his boldness as his intention. In the moment, she wasn’t put off by it, but she also wasn’t interested, primarily because she couldn’t picture herself with a man who was a good 20 years her senior, but that feeling was about her, not him.

If the request was about what HE wanted, she and I agreed that it was pretty impressive that he put himself out there like that, just going for what he wanted.  What admirable chutzpah! I guess at his age, he’s figured out that If you don’t ask, you don’t get.  You don’t live that long and not learn that lesson. I’m sure he knew it was unlikely that she would take him up on his offer, but if he was going to wait for her to make a move, that definitely wasn’t going to happen.   

And if the request was solely about her, he truly is a good friend, and she feels very lucky to have him in her corner. Hopefully the two will move forward enjoying one another’s company as they always had, despite the possible contrast in feelings.

I ran into her a couple of days later and asked how it felt being the object of desire. She then asked me if I thought he was her target demographic now…should she be expecting to attract more 80+-year-old suitors?

Either way, she was smiling.