Starting doubts young on May 25, 1998…

Dear Breakup Girl,

Hi. I am 14 years old and even though I shouldn’t worry about guys, I do. Right now I have a boyfriend. This is the second time I have gone “out” with him. He told me that he never thought he was good enough for me, and to his and my dismay, I am starting to believe it. My friends say he isn’t good enough for me, too, and that I could do much better. Complete and utter strangers that I have never seen before in my entire life tell me I could do much better. I want to follow my heart and do what my heart tells me. But I am not sure exactly what my heart is saying. Even though I am only 14 and probably insignificant to you adults, please help!

— Young, Naive, and Confused

Dear YNC,

Okay, first of all, you are hardly insignificant. In fact, teens and adults pretty much have the same problems; it’s just that teens have them in smaller units of time (e.g. “I am hopelessly in love with my girlfriend of three days;” “It’s 3:15:29 and he hasn’t called since 2:47:31 — should I dump him?”). A grownup would have written a letter with your exact question after, like, eleven years.

Anyway, your question. Um, were you a guest on a daytime talk show? That’s the only way Breakup Girl can fathom total strangers telling you your boyfriend’s not good enough (“Girl, toss that chicken dinner and get yourself a winner!”). To be sure, this whole “good enough” thing is risky, highly subjective territory, but if, like, the whole town is turning out to give you their opinion, maybe there’s something to it. Never mind the strangers, ask your friends: “What do you guys mean, not good enough? I need specifics.” Then listen. To them and to your heart.

Love,
Breakup Girl

Madonna? Whore? It’s not so complex on February 16, 1998…

Dear Breakup Girl,

I have been celibate for six years. Why? The one-night stands got old a long time ago (I’ve been sexually active since age 16), and the chance of AIDS is simply too great to risk my life on a piece of plastic. My buddies ask me, “Why don’t you just get a girlfriend? At least you’d get laid.” However, I can’t justify dating someone solely for the purpose of having sex — it would be an empty relationship at best, and ultimately doomed to failure.

Also, most all of the women I meet nowadays, in my age group (late twenties), quite often have morals lower than the average college jock. I simply can’t imagine that type of woman one day becoming the “mother of my children.” My friends tell me my standards are too high, and that I’ll never find anyone who will “fit the bill.”

Should I lower my standards? Am I being unrealistic? Is wanting a reasonably attractive and intelligent woman, with morals, a sense of humor, and not of baggage too much to ask these days? Right now, my focus is on developing my future so that if/when I meet “Miss Right,” I’ll be financially prepared to provide a comfortable life for ourselves and our children. In the meantime, it’s difficult not having anyone with whom to share things. It can become quite lonely at times. I’ll admit, my standards are high. I may expect a lot, but it’s only because I have just as much to offer. What’s your opinion?

— Hopeful

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Doubt sets in on January 9, 1998…

Dear Breakup Girl,
I fell in love with a 3-year-old (not literally) and I thought he was my knight in shining armor. I was seriously disillusioned the other day and now I’m not sure how to feel. Help!
— Sarah

Dear Sarah,
Standards, yes. Larger-than-life expectations, no. Listen, sistren, we have to relate to boyfriends as bonuses in our lives, not as Bob Villas who are going to spackle and caulk and make it look like everything’s all pretty and together. When we think, “Oh, if I can just have this boyfriend, then my life will be complete, world suffering will cease, and Buffalo will win the Super Bowl,” then of course disillusionment strikes — maybe even in the wrong place and for the wrong reason. So chalk this one up to “Whoops!” and start looking for someone whose personality type falls somewhere between the age three and medieval.
Love,
Breakup Girl