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.”

(more…)

Getting un-stuck on June 15, 1998…

Dear Breakup Girl,

You may remember me as the one whose boyfriend dumped me by cassette tape last year [that’s another story for another column — BG]. Since then we have broken up and gotten back together probably five or six times. After the last breakup we decided to be “friends” but started having four-hour-long online conversations that revolved mostly around cybersex. Perhaps I can be forgiven for thinking that this was going to be the beginning of the NEXT phase of our relationship … until last week when I forced the issue and flat-out asked him if he’d already found someone else that he was seeing…and he said yes. When I said, “You’ve been having those conversations with ME and seeing someone else?” he told me to stop giving him my “self-righteous bullsh*t.” (Keep in mind we’ve been seeing each other on and off for four years.) Anyway, my question — yes, what IS my question, you are asking — is, even though the guy is a louse, and seems incapable of being honest with me, and clearly doesn’t care much about me…WHY CAN I NOT SEEM TO GET HIM OUT OF MY SYSTEM? Thanks for any insight you might have: your website, Jonathan Kellerman books, and Haagen-Dazs “Dulce de Leche” ice cream are the only things keeping me going right now.

— PerpetuaG

Breakup Girl’s response after the jump