Dear Dategirl, A young friend and occasional co-worker has started seeing

Dear Dategirl,

A young friend and occasional co-worker has started seeing someone I briefly dated. I know you’re probably suspicious that I’m writing because I’m jealous. I’m not. I’m married now, and very happy.

Here’s the thing. He is 11 years older than me, and I’m 39 now. She’s 24. He actually dumped me and his last few girlfriends because we were “too old” 
for him. Yes, the jerk actually said this. I was 34 at the time, and none of the others were any older.

Besides being an ageist, he’s never had an actual job—it’s always these shady quick-money schemes that never pan out, so he’s constantly borrowing money to stay afloat. He even talked his mother into liquidating her IRA. As far as I know he’s never even had a bank account or paid taxes. And sexually, he pushed me a lot further than I was comfortable with, and got very cruel when I refused to go along with what he wanted me to do.

Before they started seeing each other, she asked me about him, and I was honest to a point—but didn’t tell her the less-savory stuff because I didn’t see any reason to. It never occurred to me that she might date him. This girl is beautiful and intelligent. And so young! He’s not even a good-looking geezer, and I’ve been there so I know that his powers of persuasion don’t lie between his legs either. If he were rich or handsome, I could understand the attraction, as shallow as it might be. But this?

Now that she’s going out with him, I feel awful for not giving her full disclosure. I’m afraid that if I do now, I’ll look like the spurned ex. But I feel guilty and also mad that he’s getting one over on such a nice young woman.

—Do I Tell?

The good thing about the young is that they are extremely resilient. So hopefully when she finds out he’s a pervy part-time Amway salesperson living off his mother’s retirement account, she’ll bounce back and be no worse for the wear.

Whether or not you fill her in further depends—how close are you? Given your age difference and the fact that you had no inkling she was interested in him, I’m guessing not very, in which case I’d keep my yap shut unless she asks. If she asks, all bets are off, though there is a good possibility you’ll be discounted as a disgruntled ex. So do your best to maintain a neutral tone as you relay the story about how he tried to bully you into group sex with his half-brother and -sister.

Tell her you’d originally spared her the worst of it because you had no idea she’d be interested in someone so . . . seasoned. And who knows?—maybe it’ll work out for Pattycakes and Pepaw. After all, she won’t be “too old” for another 10 years.

Just keep in mind that if you do wind up spilling the dirt, he may go ballistic. A person capable of gutting their own mother’s IRA is ruthless and obviously ready to do anything to get what they want. Honestly, I don’t hear much that makes me clutch the pearls, but that did it. On the bright side, most of us—including you and me—have dated chumps at one point or another. I’m sure she’ll survive—and when she comes out the other end, you guys will have plenty to talk about over canasta and prune-juice cocktails.

Want more? Listen to Judy on The Mike & Judy Show, follow her tweets @HitOrMissJudy, or buy her book, The Official Book of Sex, Drugs and Rock ’n’ Roll Lists.