Crushed on September 7, 1998…

Dear Breakup Girl,

My dilemma sounds a lot like the movie “The Object of My Affection.” You know, the one where Jennifer Aniston falls in love with her gay best friend, played by Paul Rudd? Well anyways, my problem is that I have a huge crush on my guy friend. He’s wonderful, sweet, and shy. We can talk about anything with each other. The problem, as you probably guessed, is that he’s gay. Well, actually, he’s just very confused. Lately, he says he’s been experiencing an attraction to other men, and this really concerns and scares him. But I’m completely in love with him, and I don’t know what to do. He thinks there’s also a chance he’s bisexual. Should I be hoping for this? Is it possible to have a meaningful relationship with someone who’s attracted to both sexes?

— Paige

BG’s advice after the jump!

Stuck in the middle on June 29, 1998…

Dear Breakup Girl,

Here’s the scenario. “Harry” and “Sally” are longtime friends in uncannily similar lines of work. Harry, who’s oozing unrequited smooches for Sally from every pore, finally busts a move just as Sally leaves for a job abroad for several months. She decides this is plausible, goes along, and they long distance it quite happily for awhile. Then they spend the summer working together, are actually in the same place, and Sally gets the wiggins. They travel through Europe together, on a Eurailpass to emotional hell, and eventually Sally pulls the plug. This being the real world, Harry’s seriously bruised–not the Billy Crystal kind of cutesy angst that ends in a charming speech that woos her back. Rather, they avoid each other for the better part of the year, then slowly start becoming friends again. But Harry, underneath the bruises, still oozes. (Vile, I know, but you know what I mean.) He’s a man of infinite braveness, so he starts blurring the ol’ friendship lines. Sally’s not sure what to do: she’s spooked about ending up alone, Harry is indisputably a great guy, and on paper it should be perfect. Yet: wiggins, which sometimes lift when she just enjoys hanging out with Harry, or sometimes return when she gets critical for him or starry-eyed for some perfect Mr. Right who’ll make her melt. Sally’s now out of town for the summer, there’s still no resolution, and Harry’s still twisting in the wind. AND…I’m the one whom Sally calls for a shoulder to be confused on. What do you think she should do, and how, as a friend, might I effectively help guide her in that direction?

— ABC

BG gives advice to the advice-giver after the jump!

Put out of her misery on June 29, 1998…

Dear Breakup Girl,

I’m SO in love with this guy at my school. We have a REALLY small school, so everybody knows everybody else, and their business too. This means that “my guy” knows I like him. He used to flirt quite a bit with me. Then my friends told him I liked him. They told me that they told him. Then, one day out of the blue, he told some of my friends that he doesn’t like it when I flirt with him, and that he doesn’t like me “in that way.” They told me for one reason, and one reason only, so I wouldn’t get more hurt in the long run. My friends are very sensitive and caring, so I KNOW they’re not lying. I’m still hurt by this. Every once in a while he’ll talk to me, but not very often. Now that summer is approaching, and both him and I live on farms, we’ll NEVER see each other. I’ve had loads of guys ask me out before, it’s just that I only like one guy, and I CAN’T HAVE HIM!! How can I go about getting him to like me?? How can I get him to ask me out?? PLEASE HELP ME!!

— Hurt and Confused Chick

BG’s advice after the jump

Classic advice from April 13, 1998…

Dear Breakup Girl,

How am I supposed to act around the guy I love (he knows I love him) when he has told me he loves my worst enemy?

— Kitty

Dear Kitty,

Jealousy, my dear, is your worst enemy. Act — as in Best Actress in a Drama– like it doesn’t bother you.

Love,
Breakup Girl

One of our all-time faves from January 19, 1998…

Dear Breakup Girl,

Why my best friend (is a boy) don’t like me but I love her. GOODBYE. (I am a French girl.)

Kiss.

— Aurelie

French Girl, step away from the hermaphrodite!

Love,
Breakup Girl