Here's the deal: Mom just spilled the beans regarding her new boyfriend. Dude is 27! That's three years younger than me! She has been seeing him for 10 months but until today had not told me or my brother, I presume out of fear of a bad reaction on our part.

The thing is, I'm not entirely sure how I feel about this. On one hand, mom is a wispy, youngish, 50-year-old woman/gypsy fashion priestess who can do as she pleases, and I'm her adult son who has no business judging her. I'm well past the age where infantile jealousy should be playing a part in my reaction, right? And after seeing her in one failed relationship after another, I should be only interested in her happiness. On the other hand, the whole situation makes me deeply uncomfortable, on multiple levels.

First, the guy is younger than me by three years. I don't know how to expand upon this other than to just repeat it over and over: the guy is younger than me by three years.

Secondly, she's had relationships with younger men before, but usually during very unstable periods of her life. When I was just finishing high school, she was struggling with addiction and there was a 21-year-old blues band bass player shacking up with us. A few years after that, a 26-year-old con-man who stole her life's savings. While none of these guys were old enough to be her son, they were all closer to my age than hers.

Third, she seems to swing from one extreme to the other, in relationships either with men old enough to be her father, or young enough to warrant the cougar moniker.

I'm not sure what my issue is here, Dan, but I'd like your help. When I was younger, her relationships with younger men bothered me to the point that I managed to get myself all messed up in the head, and, throughout my early twenties, many of my own relationships were severely dysfunctional. I don't feel anywhere that uncomfortable with this, but it does dredge up some old, weird emotions. I guess I'm not really even asking for advice, just your opinion. I know cougars are cool nowadays, and love conquers all, and age is just a number, but are there certain circumstances under which I'm allowed to be a little freaked out by this? What's the damned protocol?

A Cougars Eldest Son

My response after the jump.


First, cougars aren't cool—cougars are a myth. I read it in the Daily News. Technically speaking, ACES, sociologically speaking, your mother doesn't exist. Heavy.

Second, just as your mother is allowed to do what she likes—old men, young men, blues men, con men—nothing in the damned protocol says that you're not allowed to have feelings about what and who your mother does. And it sounds like you have some old, unresolved and/or unexpressed feelings about the chaos your mother's love life visited on your childhood. So why not tell her something like this: "Hey, mom, I'm glad you're with someone you like, and I'm glad you're happy, and score one for all the fifty-something women out there whose husbands left them for twenty-something bimbos. But I gotta say that your new romance dredges up some unhappy memories for me. Your boyfriend isn't responsible for what happened decades ago, I realize, and there's nothing you can do about the old days, and I don't think your intent was to created chaos and grief for your kids. But your love life was messy, it impacted me negatively, and, well, I just wanted to get that off my chest."

If your mother has any sense—and that's a big "if," I realize—she'll apologize and you can guys commiserate about the string of assholes she dated back in the day. Her apology won't rewrite the past, of course, and it won't magically make you feel any more comfortable about your mom's present. But it will carve your issues about your mother's love life into two separate, smaller, and more manageable chunks: residual anger about your mom's past boyfriends, freakiness about her current boyfriend.

And look on the bright side: you don't have to live with her current boyfriend, her next boyfriend, or the boyfriend after that.