Making a move on November 2, 1998…

Dear Breakup Girl,

I guess this question isn’t too hard to answer. I’ve liked this girl, let’s call her Joan, and for four years now I’ve been crazy about her, but I never had the guts to really go for her. I’ve since supressed all my feelings for her because I don’t feel I’m good enough for her. So, NO ONE knew that I had these feelings for her. Joan’s the sweetest, kindest, most beautiful, most perfect girl in the world, but she’s just a regular friend to me and that fact is killing me.

I’m not the ideal guy for girls. I’m the quiet guy who no one really bothers to talk to (hardly popular), except to ask for help on a homework assignment. I guess you can call me a nerd, but I’m not that dorky. Her friends can stand me, but they don’t really enjoy my company if you know what I mean.

Well, I know for a fact that Joan doesn’t like me in that special kind of way, and I need to find someway to let her know how I feel without completely scaring her away. I don’t want to lose her friendship. I talk to her whenever possible about little things and I spend as much time as possible around her without seeming conspicuous. I call her from time to time just to talk. I make up some excuse and ask about what assignment we got from which class and then go onto other, more casual things.

Joan’s been in a few bad relationships before where she was the one who got hurt each time. I just want to show that I can be that person that she’s been looking for.

Joan knew that I liked her a year ago from a big hint I gave her, but that was as far as I got. From what her friend said, she wasn’t disgusted with that thought (which is good), but she wasn’t excited either. I’m not sure whether or not she still thinks that I like her, but I still do. I guess that’s all I can say right now. Please help me.

— Jonathan L.

Dear Jonathan,

Let’s just say for the record that helping with homework is not always a bad place to start.

But you should also check your own grammar. I’m quite sure that Miss Joan is fantastically sweet, kind, and beautiful. But gramatically, Jonathan my man, no one is “most perfect.” And human-ly, for that matter, no one is “perfect.” (Even David Duchovny has made foolish choices.) Especially someone who you “know for a fact” doesn’t like you in that “special kind of way.” I’d call that a major flaw.

I’d also bet that, unless Joan is a dim bulb — which doesn’t seem like your type – she knows you LIKElike her. And she knows that you’re a good person who’s not just out to jump her bones. You’ve made your trusty friend point quite well, I’m sure.

So I’d say you’re left with two choices:

1. Ask her out. Sure, you might be the person she’s looking for, but if she hasn’t acted on that yet, you might need to upgrade your image from assignment-checker to asker-outer. YIKES, yes, but look at it this way: an invitation (“Joan, would you like to go see I Still Know What You Did Last Summer?”) is a way less scary (for both of you) way of “letting her know how [you] feel” than an announcement (“Joan, I need to let you know that I’ve been crazy about you for four years.”)

2. Keep doing what you’re doing … but less. You have found a way to be a pleasant presence in her life, and to get a flirty fix for yourself. But is it really working for you? As long as you’re Joansing, you get to work the martyr/savior/tutor angle, but other than that, it doesn’t necessarily get you anywhere. I’m sure your taste is good, kiddo, but again, check your judgment: you’ve spent four precious years having only excuse-based conversations with someone who — according to you — is at best “not disgusted” with the thought that you like her and whose friends can at best “stand” you. It is she, Jonathan, who is thus “not good enough” for you. I don’t mean she’s a bad person; I just mean that as far as Breakup Girl is concerned, this crush may not be the world’s best use of your time and energy and heart valves.

Here’s your homework assignment: think about who and what around you do you not notice when you’re phoning Joan. My guess is that there ARE folks, friend-types and possibly otherwise, who DO bother to talk to you, but you’re busy making up excuses to call the Joanster. Which is a great way not to have to talk to them — or to have to start new conversations yourself. So I’m not going to tell you to somehow terminate your crush, but I am going to tell you — unless, of course, you go with Option 1 — to let it breathe on its own now. Do less work. And next time write to me about someone who’s most … excellent.

Love,
Breakup Girl