Adapted from a recent online discussion.
Help Mom explore her dating choices
Q: My mom and I are incredibly close, and we talk about everything. However, we kind of clash about one BIG thing: who she dates. She tells me all about what kind of guy she likes and how she wants a man who complements her lifestyle (classy and adventurous), yet she keeps bringing home losers — there's really no better way to put this. I mean, these guys are everything she said she doesn't want, and if my boyfriend were like this, she would have nothing to do with him.
They're typically way older than she is, not adventurous at all, not classy at all, not nearly as intelligent or attractive as she is, and they generally just don't complement her. Example: She dressed up for a date, and one time the guy wore windbreakers.
I would care a lot less if she was just casually dating, but she keeps talking marriage with these guys and then saying what a loser each of them was after they break up. In the past, I've been very forthcoming about my feelings and it would hurt her, so my new method is to stay out of it. But I'm worried that if I don't tell her something, she'll end up marrying one of these guys and then will end up unhappy (signs she shows while they're dating).
A: I started an answer, but backspaced because I need to say this first: The windbreaker example is terrible if your intent is to prove these men are "losers." As a compatibility measure, it's fine, but are you really judging the character of these men by such superficial standards?
If so, then I'm going to suggest as kindly as I can that you and your mom perhaps share a people-reading disability, where you mistake a tuxedo for "class," whatever that is.
And that could indicate a chasm between what you two regard as a sign of quality, and what really is one. This could easily stem from a family's emotional pattern — and explain why you and Mom are in this pickle to begin with.
There's also this: You and your mom apparently want her to date James Bond, and, unfortunately for you both, he's fictional. Consider that your mom is dating the men reality provides for her — the men who are willing to ask her out, or even the ones she feels comfortable approaching.
Regardless, it sounds as if you have the right idea in deciding not to get up in her grill about every guy she dates — but there's one more choice available to you, if you haven't tried it yet: calling attention to the pattern versus the guy.
By that I mean, instead of challenging (and forcing her to defend) This Guy or That One, express concern that with every guy she has chosen lately, she has broken up and cried "loser." Express sympathy for her string of disappointments, and ask if there's a common denominator she might have missed.
One caveat: You get to do this once. Dwelling on it beyond that, unless she invites you to, is a boundary violation. This is your mom's life, and it's not your job to prevent her from marrying one of these guys. It's just not.