An Interview with the Boy (Now Man) Who Rejected Me in Seventh Grade

Illustration for article titled An Interview with the Boy (Now Man) Who Rejected Me in Seventh Grade

Of all the emotions, it’s humiliation that scars the most deeply. The memory of an embarrassing moment that happened decades ago can still stop a person in their tracks and devastate them for days, weeks, or even a lifetime.

I remember the most humiliating moment of my life in what feels like cinematic detail: Riding a chairlift on a crystalline night during a school ski trip in 7th grade, I asked my friend Zach if he would go out with me. He said no. Then, in a frantic rush to disguise my embarrassment as good natured indifference, I missed the opportunity to dismount the lift and was forced to ride all the way back down. Because it’s so rare to see someone riding the wrong way on a chairlift, I became a bit of a spectacle. The skiers and snowboarders riding appropriately upward saw me and pointed. They laughed. They delightfully shouted “Look!” at their friends.

As I rode down, my stomach was twisting so hard that it felt like it was about to crawl out of my mouth. I had just been rejected and potentially ruined a friendship. Worst still at the time, I had risked my reputation: Zach was free to tell the whole school what I had done. The riders pointing and laughing didn’t know about what had happened or what was about to happen to me, but somehow—in this farcical moment—it certainly felt like they did.


I avoided Zach for the rest of the night and planned to avoid him for the rest of my life. I remember laying in bed the next morning and pushing a thumb tack into the pad of my finger—not hard enough to break skin, but hard enough that it slightly hurt—again and again to distract myself from the agony of utter humiliation. I assumed that when I returned to school on Monday, things would only get more dire.

But for a middle schooler, Zach was incredibly kind, which is probably why I asked him out to begin with. Displaying a compassion beyond our years, he kept the incident to himself. My best friends never learned of it, nor—as far as I know—did his. In the following months, he would smile and say hello when we passed in the halls. Within a handful of months, maybe a year, we resumed our friendship with everything and everyone moving on—at least outwardly.

In truth, it wasn’t until well after high school that I could speak openly about it to anyone, let alone someone Zach and I knew in common. In the immediate years following, I was terrified that Zach would think that I was constantly yearning for him, that during middle school games of Spin the Bottle, I was praying for my spin to land on him. (Really I just wanted to make out with anyone.) Later, even in college, I still felt embarrassment out of habit. For the longest time—far longer than necessary or maybe even normal—the story loomed as an example of extreme failure: failure to get a boyfriend, failure to handle rejection, even failure to dismount a stupid chairlift.

It’s been about 17 years since Zach turned me down with a polite “I don’t think I’m ready to date.” Now an adult woman who has both rejected others and been rejected several times since, I can look back with nothing but affection and maternal pity for young me. Still, though, I find myself revisiting the moment frequently; lately I’ve wondered if Zach, too, considered the experience as formative as I did. If he ever thought about it at all.


It’s been a few years since we’ve spoken, but through social media and word of mouth, I knew that Zach has formed a good life in a larger city (beyond the mole hills Wisconsin tries to pass as ski slopes). He has a beautiful fiancée, a good job, and—when I contacted him out of the blue to request that he revisit my young life’s most painful moment with me as the only other person privy to it—he responded with the same grace that he’s possessed since he was 13.

“Hey Maddie!” he wrote back. “I feel sad to know that I was involved in your most embarrassing moment. But also honored.”


He should be, especially considering that he comes off tremendously well! After a few more friendly emails, I sent him a small questionnaire, which he responded to honestly and openly. My questions are in bold:

Do you remember when I asked you out on the chairlift in 7th grade?

Yes, of course I remember this night. Though you may have assumed otherwise, this experience was actually rather impactful for me as well.

If yes, what do you remember about it?

It’s going to sound strange, but when I think back to that night, the emotions are much clearer than my memory of our interaction. I hope that makes sense. The funny thing is, I remember you asking me out, but I can’t actually remember what I replied to you. Did I say anything? I can still see you fading into the darkness on that chairlift.

How did you feel when it happened?

I guess there’s no reason not to be honest. I felt really bad! I felt guilty, I didn’t want you to feel hurt. I felt sad seeing you riding alone on that chairlift—it was a long way to the bottom of the hill.

One thing that meant a lot to me both at the time and after was how you never made fun of me, told a bunch of people, or made a big deal about it. Do you remember if that was a conscious decision on your part?

Not really a conscious decision, I don’t think. I appreciated the importance of what had happened, and had no interest in causing you any further discomfort.

Do you remember any awkwardness in the aftermath?

Um, yes I do. I really don’t have much memory of the immediate aftermath, but I did perceive some awkwardness when I saw you from time to time in the years afterward. I never really knew if it was something that only I was feeling, or if you sensed some awkwardness too.

Have you thought about it since?

Yeah, sure, I’ve thought about it. It was actually a quite unique event in my life. So thank you for giving me such a remarkable memory!

When you look back on our friendship, is that the memory that stands out the most?

Hmm, well, it definitely comes to mind…

If no, does anything else pop out in particular?

Yeah, I remember you at Camp Anokijig! Acting crazy and having a good time. [Author’s Note: A great reminder that summer camp confidence and school year confidence are not the same thing.]

Do you have a similar memory that happened to you that you’d want to share? (It’s okay in the answer is no!)

I’ve been turned down in romantic situations more times than I could list here. A party a Roscoe’s house where I tried to kiss [our classmate] Amanda, and she rejected me, saying that she didn’t want to ruin our friendship. That was kind of bad. Oh, and I also tried to kiss [our other classmate] Claire and was turned down. There are more…


While contacting Zach was perhaps just an exercise in extreme narcissism, the results were incredibly heartwarming for me. It’s rare that we get to (or want to) revisit a painful memory and discover a different perspective on it, but doing so somehow feels like confronting the deepest fear of 13-year-old me. It’s a confrontation that she deserved as an award for her bravery (it’s hard to ask someone out, especially when you’re barely a teenager, and even harder to get turned down) and needed for terribly fragile pride. She couldn’t do it for herself then, but I can do it for her now.

Since talking to Zach, the memory has taken on an aura of tenderness rather than humiliation. Zach and I now exist on entirely separate paths that—apart from the occasional email or run-in over the holidays—will likely never converge again. But as is the case with all profound human interaction, we can’t escape being bound by this incredibly specific and unique moment in time, nor can we escape the web of the other embarrassing/painful/thrilling/happy/tragic moments that create the maps of our lives.


But now, looking back, why would anyone want to?

Managing Editor, Jezebel

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When I was in the eighth grade I had a huge crush on a friend of mine. After letting him know, he told me that I was too dorky for him and that he needed someone cuter to kiss.

Fast forward four years later. I had just finished taking my portraits for senior year and was walking through the mall with a friend when who catcalls me? Yep. My eighth-grade crush. He asked me for my number, told his “boys” that we were “tight” back in the day and that he always had a thing for me.

I never gave him my number.