Sexting Miss Robinson on September 21, 1998…

Dear Breakup Girl,

I’m fifteen, my friend D is fourteen, and Kay is twenty-six. D met Kay online awhile back. She’s rather the party-have-sex-with-everybody type of person, and he and she have had their fair share of cybering/phonesex (she called him; his parents are very strict). Now, I wouldn’t think anything of it, except for the fact that Kay’s birthday is coming up, and D is planning on buying her a gift. However, the gift that he wants for her is a $120 painting (plus shipping). Remember that he’s only fourteen, and he doesn’t even have a steady job. I’m probably just being a friend giving unwanted help, but I wanted to hear your perspective, BG.

— T in Ohio

Dear T,

Okay, yeah, eeeeuw. Belleruth and I struggled a bit with this one.

First, before we get to the creepout part, we concede two things: (1) in BR’s words: “If it doesn’t get weird [too late?], the world being the way it is, a shy, awkward 14-year-old can gently induct himself into the world of sex online without getting too banged around, and avoid diseases too. Also, (2) I can see why he’d want to get her something “big.” He’s probably thinking: “Wow, she’s old, I can’t just buy her, like, a Care Bear. Instead, I’ll buy her an expensive, sexy, soft-black-velvety … painting of the Care Bears. And then have it shipped because it’s too big to schlepp on my Huffy.”

As for your plan of action, here’s what we’ve got so far. BR says: “I dunno about doing anything at this point other than telling him once that this woman sounds like a sicko and the whole thing sounds like a bad idea. I’d ask him what kind of a 26-year-old woman hangs out with 14-year-old boys — I mean, Breakup Girl loved Leo on Growing Pains, but she didn’t, like, buy him stuff — and not men her own age. I’d tell him he’s gonna miss that $120 real bad later on. But then, I’d wait and see. If he can come up with that kind of cash, let him blow it on this babe. How else is he gonna learn? I suppose if he keeps sending her expensive stuff and goes through every cent he has, or if this thing escalates and she wants to meet him, then it’s time to intervene more aggressively, bust him to his parents, etc. I’m assuming that you have D’s confidence and will continue to.” Until further notice, try to play the role of less-strict parents, the kind that (within reason/safety, of course) let you mess up — and wise up — all by yourself.

Love,
Breakup Girl