Sex + Love

How (Not) to Impress Your Crush

Dumb/amazing stuff we’ve done in the name of L-U-V.

Illustration by Marjainez.

Illustration by Marjainez.

When I was 13, I went to Canada to spend two weeks at my aunt and cousins’ house. I visited every summer, but this year felt different: I hadn’t kissed a boy yet, and I thought maybe I would meet a cute, exotic guy on my trip and we could have a summer fling!

Believe it or not, fate delivered. My cousin John, also 13, had a new best friend, David, and—HEART ATTACK!!!—he was the cutest boy I’d seen in my entire life. He had shiny brown hair, green eyes, and a dark tan from spending the majority of his life on a skateboard. David practically lived at my cousins’ house: He came in through the back door around breakfast time, hung out all day playing video games in the living room, and sometimes even spent the night.

I gobbed on a lot of eye makeup and lip gloss before these visits, which I would spend walking walked past the living room 20 times an hour and laughing extra-loud whenever David made a joke at dinner. To say that he ignored these efforts would be a gross understatement. He didn’t even seem to realize I existed.

When I pressed John for details about what kind of girl was “David’s type,” he shifted uncomfortably and said, “I dunno…fun girls? Like, adventurous ones, I guess.” “Adventurous girls,” huh? Was that all? I could be adventurous!

One night, we all piled into the back of my cousin Michael’s van (I tried to sit next to David, but John sat between us) and drove to the side of a deserted highway to go bridge-jumping, which is exactly what it sounds like: hopping over the guard rails on a bridge and plunging into the lakes and rivers below. As I peered over one such railing, David, wearing only his swim trunks, stood next to me and did the same, which made it hard to focus on the water as it shone in the moonlight. He was so beautiful.

Michael began to explain the rules to new jumpers like me, but I wasn’t really listening. I snuck another glance at David. He looked nervous. Ha! I’d show him adventurous. Without waiting for Michael to finish his explanation, I climbed over the railing. Jesus, it was high. But I had to be first—for LOVE. “Hey!” Michael yelled. I put my hands over my head in a dive position. “Not yet! Hey!!”

It was too late. I sailed through the night air for a frighteningly long time before hitting the water, which was freezing and endlessly deep. OMG, WAS THERE NO BOTTOM? As I finally broke through the surface, I expected David and my cousins to erupt into cheers, but Michael was furious. “WHY DID YOU DIVE HEADFIRST?” he shrieked at me from the bridge. “YOU COULD HAVE DIED! THERE ARE ROCKS DOWN THERE!” I climbed back up to the bridge, grinned in a devil-may-care way at David, and said, “Pretty crazy, right?” But his face, like my cousins’, was ashen, and for the rest of the trip, he referred to me as “that crazy girl.”

I was furious with myself. I could have dashed my brains onto the rocks in the waters of Canada for a boy who didn’t even like me!

My only consolation was that I couldn’t be the only one who had gone to such great lengths to impress a crush. I recently asked the Rookie staff for tales of their own dunderheaded attempts to be noticed by their objects of desire. Sweet Lord, the things they told me. Read on, lest you repeat their lovestruck misadventures/hijinks.


As a high school sophomore, I was in an open relationship with a boy named Alex. One of our relationship guidelines was that we could hook up with anyone we liked, “but they can’t be better than me.” There’s a lot wrong with this rule, not least that the definition of “better” was totally up for interpretation.

At one house party we attended, Alex told me that a girl he had a huge crush on had an impressive skill that I lacked: They sometimes played games where they dared each other to eat or drink anything…and she just did it, instantly. Ramekins of coleslaw! Raw sushi! Nothing was inedible to this girl. “And she drank a pint of milk,” Alex added.

I responded to this by immediately going over to the refrigerator, withdrawing a gallon of milk, sitting down at the kitchen table in the middle of the party, pouring myself a glass of milk, and pounding it. I repeated this exercise until the entire gallon was gone. People stood around the table in horror, like, “Your gastrointestinal system is going to give out!” It didn’t. “You’re going to puke!” I smiled serenely. Alex stared at me with awe, love, and fear as I announced, “I’m NOT going to puke.” And I didn’t. Alex and his new fling were finished.

Alex and I broke up that summer, but I never stopped carrying a torch for him. Two years later, he was on break from college and showed up to a late-night diner excursion. I saw my opportunity to once again prove my undying love. “Alex, look,” I said, holding a tin carafe full of cream that had come with our coffee. He laughed nervously. “Remember when I drank that entire gallon of milk to prove that I loved you?” He was silent. I knocked back the whole pitcher of slimy, lukewarm cream (god knows how old it was). Then I looked him right in the eye and said, “I love you.” He could barely look in my direction for the rest of the meal.


I’ve got two. First, when I was 15, I met a group of guys from a different high school who seemed so much cooler than any of the boys in my classes, and I had crushes of varying degrees on all of them. They were really into hardcore music and were in a band of their own, so I started going to all-ages shows, ordering band T-shirts online, and pretending I could distinguish one screaming vocalist from another. I was so eager to infiltrate their circle that I told the guys I had experience shooting band photography, and I ended up fumbling through a shoot with five gangly boys with lip piercings as they leaned moodily against a graffiti-covered wall. Very edgy.

I didn’t know what I was doing with even the most basic point-and-shoot camera, but the resulting pictures got tons of likes on the band’s MySpace page, and that earned me points with the guys. They must’ve figured the blinding flash I used was an artistic choice—not just a function I didn’t know how to turn off.

This phase ended pretty abruptly when, after spending my 16th-birthday money on a lip piercing of my very own, I ran into one of the guys in the band outside the piercing place. He was shopping with his mom, and he offered me no praise or attention for what I’d just done. Judging from the way his mom looked at me, I guessed his love of the scene was something he hid at home. Ten days later, I took my lip ring out, much to the delight of my own mother.

Proof that doing embarrassing stuff around your crush DOES NOT STOP when you leave high school: In my first year of college, I had a huge crush on a brooding third-year guy in my cinema studies class. We’d chat casually about the films we liked and the music videos he was making for his friends’ bands, and then I’d race home and absorb all the information I could glean from his public profile on Facebook (I was too nervous to add him).

It got to the point where I’d forgotten what we’d talked about in person and what I’d learned from my cyber investigation and, occasionally, I’d say, “I know how much you love that new Beck album!” in person, when we’d NEVER SPOKEN ABOUT BECK. He seemed kind of bemused by my dorky eagerness, but never made me feel weird about it. Perfect crush behavior!

On the last day of class, convinced I’d never see him again, I gave him a mix CD filled with embarrassing semi-romantic songs by bands he didn’t know I knew he liked. As soon as I handed it to him and saw the kind of confused expression on his face, I high-tailed it out of there, sure he knew I was hopelessly in crush with him. I’ve since bumped into him in person about a dozen times, and he’s never brought it up. Again: Perfect crush behavior!

When I was 19, I was in an a cappella group with a girl I had a crush on. We put on a concert every semester, and to promote it, we’d do a walking campus tour and sing in all of the frat houses. I knew she was into fashion, so I wore my silver sequined stilettos and spent three hours walking across campus in them. My shoes were a conversation topic for about 30 seconds, and the one compliment my crush gave me about them definitely wasn’t worth the two days I spent limping afterward.


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  • Libby August 5th, 2014 3:40 PM

    Emma, your story is the sweetest – my dad has a similarly silly-but-sweet tale about taking his trousers off in the pub and dancing in pink panther boxers to impress someone – my mum! Twenty two years after and they’re still together.
    Maybe that’s why I do so many dumb things to try and impress crushes or just erroneous cute boys? One really stupid thing I did is pretending to like stuff I’ve never heard of before to impress a really cute boy – he did ask me on a date, but in the end I got too scared to have my own opinion around him and actually discuss the things I like (he kind of shot down anything I said about books, my number one passion, and never bothered to read any short stories I liked even though I watched a football match for him!) and it soon became apparent that we wouldn’t be a good couple. I was too nervous and he was too self-centered.
    Sometimes failed attempts to impress guys work out, in a round-about sort of way, like the time I saw a cute boy in a mosh pit at a gig, joined in, and although I never got his name or number, I did have one of the best gig experiences ever! The rest of the mosh pit was made up of drunken middle aged men; without this hot beacon of teenagedness, I wouldn’t have felt safe enough to join in, but by the end I was so sweaty and exhausted that I didn’t even care about seducing him. (also – what was I thinking by trying to seduce someone at a gig? More often than not, I’m sweaty, disgusting, and stinking of beer that someone’s accidentally thrown over me.)

  • tangratoe August 5th, 2014 4:10 PM

    I am in love with this post, especially the last two stories, those just killed me
    All so relatable though… I have done many things similar to this that I am scared to dig out of my memory…like when I pretended to have watched the last epsiode of Sherlock season 2 to impress this guy, thinking I could pull it off because of having seen so many tumblr gifs about it. It went pretty well until he asked me a question about what happened after the big cliffhanger in the epsiode and I thought nothing had happened…when really everything had happened :S

  • ghostelic August 5th, 2014 4:29 PM

    there’s a mistake on the third paragraph ”David joked made a joke”

  • Abbey xoxo August 5th, 2014 6:48 PM

    I loved this article! I’m especially in love with the last sentence because it’s both very meaningful, and it reminded me of how I once tricked my family into thinking that I drank all the creamer even though I didn’t and now everyone thinks I did even though I constantly deny that I ever did and repeatedly tell my family I was trying to mess with them *exasperated sigh*

    Anyway. I love the stories! I can totally feel Tyler’s shoe pain. I’m in theatre tech at school and once I had to carry this really heavy board across the stage, and my crush offered to help me carry it, but I refused help to seem like a strong, powerful, independent woman or something and ended up with sore arms after single-handedly carrying this massive and heavy board across the stage, and the resulting romantic effect was nothing.
    But I once gave him this amazing Secret Santa gift that compiled a bunch of his favorite things, which he loved. I got a very long thank-you hug with a lot of back patting <3

  • e1znekcaM August 5th, 2014 7:39 PM

    When I was 15 I had a crush on my friend two grades above me. When he graduated from high school, I purchased an embroidered hoop with the words “musical soulmate” and an iPod embroidered on it from Etsy and gave it to him as his grad present. I also wrote a long note about how great of a person I thought he was. It seemed like a great present up until I gave it to him. Luckily I didn’t have to watch him open it, but I know he must have thought I was borderline crazy. Even though we were friends, I just know that at that point he realized I wanted more out of the friendship. He wanted to remain friends, it was clear. It made things a little awkward, but we’re still friends. I brush it off by saying at least I supported an Etsy artist. I mean, the embroidery job was awesome!

  • Me August 6th, 2014 6:53 AM

    I can totally relate with Stephanie! I used to walk by my crush’s house ALL the time. Worst thing was, he lived in a cul-de-sac, so there was absolutely no reason I could possibly be walking past his house if he had ever seen me…

  • mickeyf19 August 6th, 2014 11:41 AM

    I had a thing going on with a high school sophomore when I was a freshman, but even today I’ve never had a boyfriend so I was really obsessed with making our THING work. Y’know. By the time we were ending I was so distraught that I would sit in the room our friends hung out in after school, bawling all over everything, until he came into the room – when I climbed onto the table and did back bends exorcism style, desperate to be noticed by dear Ben.

    Also, we were going on a school trip out of town later in the year so during a discussion about hotel rooms with a few other students, Ben, and A TEACHER, I was like “yeah so hopefully Ben and I can room up together.” Jesus. I was kinda terrifying.

  • Flossy Mae August 6th, 2014 2:13 PM

    Omg I have my own one to add ahaha well about a year and a half ago I had a massive crush on this guy from another school. He was in the year below me and asked me once if he could borrow some of my old school books. Eager not to disappoint I agreed, and consequently spent a whole weekend reading and annotating Jane Eyre in great detail in different coloured pens to make it look like id done it in class – when in actual fact I’ve never even studied the book! He was very impressed though and I think he ended up passing English so I consider it a score anyway.

  • taratwinkle August 6th, 2014 5:10 PM

    “If someone likes you, they like you, even if you drink all the creamer, and if they don’t, they don’t…even if you drink all the creamer.”


  • Estelle August 6th, 2014 9:39 PM

    OM G

  • tommy shepherd August 6th, 2014 10:37 PM

    This makes me think of how back in high school I only had one legit crush, and I remember I made him a plush doll of Hayley Williams from Paramore for my crush for Christmas because he worshiped Paramore so much.
    And while he totally liked it, it did not make him fall in love with me and I still get embarrassed when I think about it.

  • Janis August 7th, 2014 6:36 AM

    SO IN LOVE ♡ with this post omg

  • Tiana August 7th, 2014 7:43 PM

    I love these stories and can definitely relate to them!
    Tiana x

  • Hani August 9th, 2014 6:23 AM

    and yet more proof that i’m not the only one perpetually single and constantly rejected by crushes