Insecurity lockdown on June 1, 1998…

Dear Breakup Girl,

This guy I’ve been dating for five months is sweet, smart, cute, loaded, calls twice a day minimum, respects what I have to say, etc. He just can’t seem to stop mentioning how many girls have the hots for him. He’ll have a business lunch and then let on that he’s a little upset cause his lunch partner was “working him” (his term). Or, he’ll have weirdness with this girl or that cause she “kinda liked him” and he “wasn’t into it.” He makes it very clear that he’s not interested in anyone but me. I just don’t get why someone so handsome and accomplished should feel the need to point out constantly how desirable every girl on the planet finds him. I have tried to tease him gently about this but it doesn’t seem to sink in, and I don’t want to start a fight.

— Liesel

Dear Liesel,

Oh, Breakup Girl could advance a million theories: he’s insecure about women liking him, he doesn’t know how to tell you how he feels so he “shows” you by telling you about the ones he’s not with, he can’t relate to women as peers but only as Theoretically Dateable People, etc. Handsome and accomplished are not inoculations against these ills; sometimes, they are, respectively, cause and symptom. Hotties (I’m told) wonder if people like them for who they really are; over-achieving can be a way of compensating. (If BG ever uses the words “relate,” “insecure,” and “compensating” in one paragraph again, tell her she needs a vacation.) Still, I’d have to go on a business lunch with him to be absolutely sure.

Anyway, you can’t use any of this information when you do the only thing you really can do: tell him gently but firmly that it bugs you. Using “I” statements will help you not start a fight. (“I” statements are the kind of thing Dr. John Gray et. al. talk about all the time. They’re when, instead of saying, “You suck,” you say “I feel that you suck.”) (In his case, “I” statements should come naturally, as my impression is that most of his sentences start that way, anyway.) Don’t analyze, don’t attack. Just say, “You know, I appreciate that I’m clearly Numero Uno here, but frankly I just get a little tired of hearing about all the women who are ‘working’ you. I’m not jealous, but it strikes me as more information than I need, and we’ve got so much else to talk about. I’d love it if we could keep that kind of stuff down to a minimum.” If that mild, straightfoward request makes you feel insecure– or if he can’t relate to what you’re saying — then you’ve got to stop compensating for both his and your … okay, I’m going to Tuscany in July.

Love,
Breakup Girl