Fooling around on October 19, 1998…

Dear Breakup Girl,

What’s a good way to tell my sweet, incredible boyfriend that I think he’s beautiful and I adore his body, even though he’s fat, and I’d like the lights on once in a while (nudge nudge, wink wink)?

— In the Dark

Dear Dark,

You pretty much already know, but I’m so glad you asked. How about saying, “Sweet incredible boyfriend, I think you’re beautiful and I adore your body. I love what we do in the dark, but I’d also love to try having the lights on once in a while.What do you think?” If he’s bashful, start with lots of candles (think: that scene in the new “Romeo + Juliet,” except without the death part). Alternatively, you could simply “show, not tell” (nudge nudge wink wink).

See, shy big/beautiful people out there? Saying, confidently, “Here I am!” — as opposed to hiding — is what’s truly hottest of all.

Love,
Breakup Girl

Back to basics on August 31, 1998…

Dear Breakup Girl,

I am 17 years old, and have NEVER had a girlfriend. I am attracted to women and all, but have never had a girlfriend. I’ve liked many girls. It may be because I am shy when it comes to women, I just don’t know. So, is this abnormal? What can I do about it?

— Mike

Dear Mike,

BG needs to know more about your technique. If any. You say you’ve liked many girls … but is BG the only girl who knows that? Look, if you’ve been too “shy” to talk to them at all, you could not be more “normal.” (Also, single.) Just listen to what the supercute Everyguys who wrote What Men Want have to say: “When men feel that spark of attraction, we become excited and nervous. … It is the woman we really want to meet who makes us tongue-tied. We erect a barrier of fear and desire that may become difficult to break through. As soon as the spark is lit, our confidence tends to plummet, we lose our rap, and we become fearful, fumbling idiots.” So now do you feel normal? (Also, hopeless?)

Listen, Mike, if walking up to a complete stranger and saying “Where do you been here all my life often?” is not your style, so be it. It’s just as well. So try to meet and hang out with people in situations where you already have a surer foothold, a more comfortable context. Thing is, though, when you LIKE-like someone; you’re gonna feel shy. It’s part of the tingle. (Also, terror.) But take heart, not flight: we actually think it’s pretty cute.

Love,
Breakup Girl

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

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