Failure and Success: Telling Someone About the Crush (Part I)

So I’ve talked about how to tell someone you have a crush on them and why you’d want to do that. I figure now it’s time I share a couple of stories from my own life. One when things went pretty darn wrong and another where they went considerably better.

A Failure to Understand

Back in my first year of college, just when I was starting to get my head clear and really start living my life as myself (as opposed to some oddly contorted version of who I and others thought I should be), I met a girl. As usual I fell for her something fierce and didn’t do all that much about it.

Mijan and I spent a lot of time together. Her and a couple of her friends easily integrated with the group I was running with. We all went out together every now and then, we all explored strange and unusual ideas, we were all friends. Coming from the not entirely self-imposed isolation of middle and high school, I was loving it.

One night, my buddy Z, being the epitome of awesomeness (which I really couldn’t appreciate quite as much at the time) loaded us all into his car to go… somewhere. Maybe it was just out to a movie, maybe shopping, maybe just a spin around town. I don’t remember. What I do remember is that there were about eight of us crammed into his Audi. Five in the back seat, him driving and two of us in the passenger seat. Most stacked two deep.

What makes Z awesome (at least in this instance) is that he orchestrated it so that it was me who ended up in the passenger seat and Mijan who ended up sitting on my lap, her head cocked to one side so it wouldn’t be pressed completely up against the roof.

Really, all the other details are a bit fuzzy. All I knew was that she was there, on my lap, and, every now and then, shed glance back, smile, and laugh a little at or contribute to the conversation that was going. I could feel waves of attraction coming off her in my direction.

It was shortly after that night that I decided I was definitely going to tell her how I felt.

I spent days psyching myself up for it. Had seventeen different segues planned, moving from telling her how I’d fallen for her the day I met her in passing at orientation and how I’d been thrilled to stumble upon her in the computer lab and ecstatic about being able to help her log in properly (leaving out the semi-obvious fact that doing so also let me get her e-mail address so I could keep in touch with her) to asking her out on a date.

After all, it was sure thing!


But I was far from solid in my conviction and still quite unsteady when it came to asserting myself in any way. Especially in matters of the heart.

So I begged my friend Chris to help me by serving as moral support. “Dude, I’m going to do something that may be incredibly stupid,” I said. “I need you there to at least watch in case it goes bad.” He grudgingly agreed and went to wait in my room.

A few minutes later, I corralled Mijan in. “Hey, can I talk to you about something?” I didn’t get a look at her face when she saw Chris was in the room, too, as I was rehearsing my lines in my head, but I can imagine she was, at the very least, a bit wary of what was about to happen.

To door closed and I launched into some jabbering, halted, lilting version of something vaguely resembling what I had wanted to say. It took maybe a minute or two to get through, but felt like days. Agonizing days. But then I got to the next to last set of words. “I really like you and have for a long time. And I hope you feel the same way…”

I paused as I caught the look of utter horror in her eyes. She took the opportunity and rendered my planned final question more than moot.

“I don’t,” she said. “You’re nice and all but I like… him.” And she looked back at my friend Chris, who I can only imagine was in almost as much shock as I was.

That’s when it occurred to me that Chris had been sitting behind me in the car that night. Every time she turned around to smile and laugh, she was actually looking over my shoulder at him. Those waves of attraction I felt coming in my direction? They were meant to hit three feet past me.

To my credit, I didn’t crumble into a ball and die right there. I felt like I would. But I didn’t. Instead, I politely excused myself. “Well, then. I’ll, uh, just leave you two to talk.” And went for a bit of a walk.

Not at all what I had planned.

In retrospect, I couldn’t have done it much more wrong without insulting her family and vomiting on her.

My first mistake was going into the conversation with high expectations. A close second was going in with a set agenda. The third? Dragging someone else into it. Fourth and finally, I was so wrapped up in what I had planned to say that I must have missed at least a dozen cues that should have stopped me before things went as far as they did.

If I was just going to confess my crush on her, I should have done so in a much more casual manner.

But my goal wasn’t to let her know how I felt.

My goal was to ask her out.

With that as the goal, I should have skipped the long, drawn out story (which I obsessed over something fierce) and just skipped straight to “Would you like to go on a date sometime?”

It would have been a lot less painful–for all of us–if it hadn’t been built up as much as it was.

When we attach so much significance to a hoped-for (or, even worse, expected) outcome, we can’t help but be crushed when things don’t pan out that way.

The whole situation could have been as simple as me asking her out and her politely telling me no. Instead, I brought it into a whole new level of pain and discomfort for three people.

I failed to understand where I was coming from. I failed to take her (or my buddy) into

It was bad, but we all recovered from it. Chris and I are still friends and still in touch. Mijan drifted out of our group as time went on, but we parted as friends. I haven’t seen or heard from her in over a decade. (But I’d love to have the chance to catch up… and hear her side of this story.)

Not all of my crush declarations have gone anywhere near this bad. I’ll tell you about one of the better ones next…

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