Reader’s Revenge: Your Worst Rejection Stories

promMonday means “Readers’ Revenge,” the weekly feature in which we turn Grantland over to YOU, the unpredictable reader. This week’s topic was Your Worst Rejection. I got a lot of good e-mails about sports rejections and job rejections, but there were so many heartbreaking romantic ones that I decided to just roll with that theme. Each week I try to come up with a lesson derived from the e-mails I received, and for this week, I’ll just hit you with a question: What’s more painful than life? (Also, the batch below concludes with what might be my favorite e-mail of all time.)

Below are the top 10 e-mails. The topic for next week will be Your Worst Job Interview. I imagine I’ll mostly get e-mails from the interviewee, and that’s awesome, but if you were the interviewer, I bet you’ve got some solid tales of your own. Send your best story to by Sunday for a chance to be as famous as Johnny Depp before his 21 Jump Street days. Stories can involve you or someone you know, and anonymity is allowed. Those with a high degree of hilarity and humiliation always do well. Enjoy!

10. My worst rejection: It is hard to choose between two stories, so I will tell you both of them. The first happened when I was 16, I was at a party with my best friend on the Upper East Side, he was there with the girl he was hooking up with and she brought a friend, I don’t remember much either of them, his girl or the friend. I remember she was skinny, not very cute, and had a very large nose.

I was (and still am) very shy and didn’t want to get rejected by a bunch of girls at the party who were much more attractive. I also figured it would be easier to go for the lower hanging fruit, so to speak. so I ask him to put in a word for me, and check out the situation. He walks over to the friend and talks to her for about five minutes and comes back and proceeds to tell [me] something I will never forget “… she said she doesn’t like you, and this bothers her, cause looks normally don’t matter to her.” I don’t think I ever knew her name and never will, but It has been nearly 15 years and I still haven’t forgotten that.

The second was later that year. I think part of what makes it so bad is it actually happened on the night I turned 17. I was away at a week-long summer camp and had gotten into a fight near the woods that spilled into the woods, and without realizing it, ended up in some poison ivy, which — the day before my birthday — decided to appear on my face. It wasn’t that bad, but definitely noticeable. So I am about to turn 17 and figure “What the hell?”, so I muster up the courage to talk to this cute girl who was a couple of years younger than me and had a reputation for being “very friendly.” So I ask her if she would like to “hang out” for my birthday, she says no and begins to cry “Because she feels so bad about rejecting me on my birthday.”

I think they are crocodile tears, but at the same time, a girl crying is every guy’s kryptonite, so the stupid sap that I am, I try to cheer her up. My best friend (same one) notices and comes over and tries to be “chivalrous” as well and stop this girl from crying. (Once again, she’s crying because she rejected me.) Well later that night, after lights out, she sneaks across camp and hops into bed with … you guessed it, my best friend. I wake up the next morning to see the poison ivy on my face has grown and now have to leave camp, get taken to the hospital, and get a shot and a prescription for steroids to help fight the poison ivy, yes this was on my BIRTHDAY!

— Shai, Jerusalem, Israel

9. I was deployed to Iraq during a pretty hectic time over there. We were working 12 to 18 hours a day doing Army stuff, which left little free time for literally anything else. A side note here: When you live your life in a vacuum like we did, any change to the norm is treated like a big deal even if it doesn’t happen to you … so when your buddy gets naked photos of his girlfriend, they are common property within 24 to 48 hours (ladies …). Meh. It happens.

I came back one day really late and hopped on facebook to see an old high school friend had added me. I had not seen this girl for like six to eight years and she had gotten hot. Like, model hot. So naturally I accept and move the forum to e-mail as quickly as possible. We talk a lot and make plans for my upcoming 15-day rest and relaxation (R&R) period back home. Long story short, a lot was promised and even more was delivered. I was elated. I got back to Iraq and for the remaining three to four months of the deployment, I was looking forward to seeing her when I got back. She bought tickets to come see me when I landed, we had made reservations for some hotel/spa thing, etc. Everything was coordinated, including where on our Division’s parade field we would meet up after the welcome home ceremony.

When we landed back in the U.S., I dutifully went to the pre-arranged spot. Nothing. I waited there about 30 to 45 minutes until the crowd had really cleared out … nothing. I grabbed my bags and hopped in my buddy’s parents’ car and went to a hotel … still nothing. I went to the hotel/spa … still nothing. Somewhat dejected, but probably more worried, I went to a friend’s house and sent her an e-mail to that regard. Two days later, I got an e-mail back that stuck out for an obvious reason: She had a new last name. Turns out she was engaged the whole time, she was merely testing the waters one more time to make sure she had the right guy.

Rejection? Maybe. But remember what I said about naked photos and our general sharing attitude? Yeah. She became instantly famous with about 300 of my closest and not-so-closest friends.

— Dan, Nolanville, Texas

8. My senior year I was kinda dating this sophomore girl named Mindy. Before our first date, her mom had me come over and talk to her before she let her daughter go out with me. That didn’t scare me off and her birthday was coming up, so I wanted to plan something special. Up to this point, we had not kissed. We got out of school early that day and we had about an hour to celebrate before I had to go out of town.

Since I was completely broke, I had to go cheap. We went to a park and sat down on a bench. I pulled out a can coke and two nice goblets (from home). Then I pulled out a 100 Grand bar that I had gotten free from a coupon from a cereal box. I arranged the two pieces of 100 Grand around a candle and lit it. I sang happy birthday and she blew out the candle. Things were going really well and I was thinking this is the day for a kiss.

I took her home and helped her bring in all the flowers and balloons that her parents and family had sent to her at school. I had to leave so I gave her a hug, but she wasn’t looking up for the kiss. I knew that “if it is to be, it is up to me.” I had to deliver a line to make her pucker up. I said, “Would you like a birthday kiss?” She responded, “Nah, I think I’m alright.”

End of date. End of relationship.

P.S. If you pick this story, I will absolutely put a link on her Facebook wall.

— Will in Folsom, California (story happened in Lafayette, Tennessee)

7. In the fall of 2000-ish, I was heading home after visiting my brother. After a quick 9-ish a.m. flight from Reno to Vegas, I find out that my flight from Vegas back to Chicago has been …

flight delayed

flight canceled

next flight delayed

next flight canceled

… to the point that by the time I get on a flight headed home, it’s 11-ish p.m. The only way I’ve gotten through this without losing my mind is by convincing myself that the extremely attractive 20-something (EA2-S) also waiting for a flight back to Chicago is obviously going to have sex with me on the plane. Obviously.

Fast-forward to the plane arriving in O’Hare at 2 a.m. Not only did EA2-S not have sex with me on the plane (since I hadn’t even, you know, talked to her), but since there isn’t a train back to the suburbs until 6 a.m., I have four hours to kill on a Monday morning in an all-but completely empty O’Hare with absolutely nothing to do. I decide that it’s in my best interests to go out to arrivals where the cars/buses/cabs pick passengers up and sit down. Well, the rest of the passengers on my flight are slowly picked-up/get in cabs/leave until the only two people left are me & EA2-S. Uninvited, she comes over and sits down next to me, strikes up a conversation, begins excessively flirting with me, laughs at all my lame-ass jokes, touches me while she’s talking/laughing, etc.

Apparently, she’s only four months removed from graduation herself, is in town for two weeks for training for her new job and doesn’t know anyone in the city — which I obviously interpret as “I would like to have sex with you for the next two weeks.” So, as the [insert rental car company which I can’t remember here] bus pulls up to take her to her rental, I ask for her number. She grabs a pen from her bag (remember, it’s 2000-ish) and tells me to hold out my hand, on which she writes …


… and gets up to board the bus. I distinctly remember staring at my hand for a couple of seconds, wondering how the hell I’m gonna call “NO,” when it finally hits me.

Me: “Wow, that’s really mean.”

EA2-S: [smiling] “I know.”


— Michael from Batavia, Illinois

6. Imagine you are from a small town in [the] South. You grew up in Texas, had owned and rode horses all of your life. You somehow get accepted to Texas A&M, and meet a girl considerably out of your league your junior year. You somehow convince her to go on a date. It goes well enough that you get a second, where she proposes a nice horseback ride. Trotting the horses back to the barn, while not concentrating on the horse, you catch in your peripheral vision a yellow blur.

This happens to be the horse’s tail that is up beside your head as the horse comes to complete stop, bowing its head and launching you at the speed of a Nolan Ryan fastball. Through the air you go, coming to rest on the ground after ripping off part of your face, separating both shoulders, dislocating your left elbow, shattering your right ulna and breaking the head off your right radius. In a cast for three months, arm locked in a right angle, your hero gets the cast off a couple of weeks early and goes to surprise this lovely girl at work. In front of roughly 40 people, I was informed now that I was “healed,” we were done.

That just happened.

— Dean H.

5. Summer of 2010. I’m traveling around in Southeast Asia with a friend, and, whilst in Thailand, meet the girl of my dreams. We immediately hit it off like we’re in a movie — I’m talking witty back-and-forth banter that rivals an Owen Wilson and/or Vince Vaughn movie. We travel around together for another few days, but then I’ve got to go home and she continues on her year-long travel-the-world adventure. But she’s also from the Bay Area, and she’ll be home eventually, so of course we keep in touch. A few e-mails a week, a couple Skype dates per month. Things are going well — the phrase “serious future” is said multiple times by both parties, and she even used “too good to be true” at one point. Oh, the foreshadowing.

After she decides to prolong her return home for another few months (she just loves living in New Zealand too much), it is decided that I will fly across the ocean and we’ll meet for a romantic week in Fiji. Talk about an inability to close. She fully intended to finish falling in love with me, but for reasons that are still unknown, she just didn’t feel the way she expected to. While on the trip, this subject was danced around under the guise of how she’s just got too much wanderlust to settle down in any sort of relationship.

I was probably in denial, but I figured it only meant I’d have my work cut out for me once she got back home. Alas, about a month after Fiji, she drops the hammer in an e-mail, explaining how the trip was an eye-opener for her, and despite the fact she never intended it to go down like this, she’s now smitten with one of her Kiwi friends. They remain “in a relationship” today. A heart-breaker for the ages, and I’m still trying to wrap my head around the whole thing.

Oh yeah, and here’s the cherry on top: I got the relationship-ending e-mail after coming home from work … after getting let go from my job! This was actually a good thing because I hated the job and I got to go on Funemployment. But still, I lost my job and my girl in the same day. Who knew that actually happens in real life?

— Mike from San Francisco

4. Last summer, I was dating a woman. I liked her. A lot. We were taking things slow — very slow — since she had recently gone through a divorce. This went on for several weeks, during which I helped her move into her house and did everything I could to show her I was a nice, decent, stable guy and not a complete dickwad like her ex.

I was, of course, doomed.

We discovered that neither of us had seen Inception, so she invited me over to her place one Sunday evening to eat pizza and watch it. I brought ice cream and whiskey — the ice cream for her (she had a sweet tooth) and the whiskey for me because I thought I probably needed to be buzzed to better comprehend a movie in which a spinning top plays a crucial role. Seriously, Christopher Nolan, fuck you.

As the movie played, she cuddled up next to me on the couch. The closeness helped keep me distracted enough so that I didn’t overly question the movie’s absurdly rigid logic of how a dreamer’s unconscious, free-wheeling, id-spewing mind works. The movie ended — the top still spinning — and she sat up to ask me a question.

“So, can I talk to you?” Because apparently we hadn’t been talking before.

She’d met somebody. A random guy in a random bar. She really liked him. She felt terrible.

I did the math. While I was helping her move and packing a car with enough jackets, dresses, shirts and sweaters to clothe a small Lithuanian village, and an accompanying herd of goats, for a month, she was seeing this guy. I felt like an idiot. The pizza and ice cream in my stomach were going all krav maga on each other. I wanted to punch something. A wall. Her TV. A baby bunny rabbit. Anything. It didn’t really matter.

She wanted to be friends. She gave me [a] hug.

I left.

We’re not friends.

I understand there might be a sequel to Inception. If it does come out, I think I’m going to skip it. I’ve seen this movie before, and it sucked the first time around. (“Hi, I’m Ellen Page. I’m here strictly for exposition. And to be cute.”)

Seriously, Christopher Nolan, fuck you.

— Anonymous

3. This is a two-part story … apparently either I’m a glutton for punishment or I just can’t take a hint. It was the end of my junior year of high school, and I was totally in love with a girl in my class. Prom was rapidly approaching, so after several weeks of psyching myself up, I eventually built up the nerve and asked her to go with me. Her response was classic; apparently her family might be going out of town that weekend, and she would let me know the next day. The next day came, and yup, they were leaving. In hindsight it’s pretty laughable, but I excused it rather easily at the time.

Now, your average guy would sensibly move on. But I’m not one to be deterred, so I spent the next six months still looking for an opportunity to get with her. Eventually the Christmas dance came around, and that seemed to be the perfect opportunity. That night came, and I planned my move. When the first slow song came on, I was gonna ask her to dance, and basically sweep her off her feet as I had been planning on all along. It was a high school dance though, so the first slow song didn’t play for almost three hours. But finally the moment came, and at the first strains of “Hero” by Enrique Iglesias, I sprang into action. I made my way across the dance floor, heading straight for my crush … until it turned into a scene from a movie.

I swear, I was halfway across the dance floor when she saw me headed for her and dashed across the dance floor; she headed straight for my best friend in the whole world, and asked him to dance. Mind you, this kid might as well be my brother. We’ve been through thick and thin, somehow survived an entire basketball season under the same insane coach, hung out every day the previous summer … you name it. And he just said “sure,” and she put her arms around his neck and they started dancing. I froze in the middle of the dance floor, and everything suddenly went all slow motion on me. I was absolutely crushed and embarrassed at the same time.

Mind you, everyone in my high school knew I was into her at this point, so the moment essentially devastated my reputation beyond repair. I shuffled slowly off the floor and because I couldn’t think of anything else to do, and to more fully encapsulate how pathetic the situation was, I began cleaning up the food with the most awkward, insane kid in the whole school … who was the only other person without a dance partner. Crushing.

It’s been four years, and I’m finally over the girl. But that moment, when she absolutely destroyed me for the second time, remains the greatest single moment of devastation I’ve ever experienced.

— Andrew M.

2. Young love can be tough. Young love can be even tougher if you’re a socially awkward, late-blooming, shy kid who just moved to a giant high school in Indiana after growing up out west. Having no romantic abilities prior to the move, when I was actually semi-popular, after the move was tougher where I had no friends to speak of. I gained most of my knowledge of courting from romantic comedies.

Making a long story short, I had developed a giant crush on a girl, we’ll call her Karen (name changed to protect the embarrassed). Beautiful, smart, fun, easy-going, the whole package. And I was head-over-heels for her. We were decent friends, frequent study buddies and we’d catch a movie together every now and then. She knew I liked her, and I probably missed an opportunity earlier in the year, but I was too much of wuss to really go for it at the time.

I finally sack up and ask her to prom. I do it cutesy style, surprise her with flowers and all that. She says she doesn’t want to go to prom at all, it was only a week or two away, she didn’t want to get a dress and deal with all of it. I’m heartbroken, but the outcome wasn’t totally unexpected.

A couple days go by, and a mutual friend of ours asks me if I want to go with her instead of Karen because she really wants to go and besides, Karen is going with Mr. Douchey McDouchenstein. Ugh, had my first panic attack.

I end up going to prom with the friend. And the whole group I’m with knows of my undying love for Karen, they’re all good friends with her, and she probably would’ve gone with this group if it weren’t for me and not wanting it to be weird.

Prom sucks, whatever, afterparty time. Now I hadn’t had much experience drinking. Was genuinely drunk probably three times before that night. But I had never had vodka. I’m fairly miserable after seeing Karen dance with her dude and word was she might be stopping by the party to hang out in a bit. I decide to drown my sorrows, seems like what they’d do in the movies. I downed three full cups of straight vodka, really it tasted pretty good. And I felt great for about five minutes after that. And then I don’t remember a god damned thing. Genuinely blacked out, I really should have gone to the hospital. I have no recollection of anything until the next day when the host girl woke me up at noon because her parents would be back soon.

Apparently, I had sprawled out on the basement floor and just spray puked everywhere for a solid few hours, and in between, wouldn’t stop screaming “I LOVE KAREN!!!!” over and over again. They vacuumed my face to get the puke off. My date hooked up with another guy [whose] date got crazy pissed, causing mass drama. When I woke up I couldn’t walk up the stairs so I crawled. I got in my car and slept till 5 p.m., and even then I shouldn’t have driven home. And they put pictures of the face vacuuming in the prom memories photo book. Sweet lovely memories.

After that, Karen didn’t want to hang out much. We’d still see each other and had classes together, and I was still quite infatuated with her for a while, but it never came to be. Those f#$%ing movies lied to me, the nerdy good guy doesn’t always get the girl in the end. Hard lesson to learn at that age. Its 10 years later and I’ve got a knockout girlfriend who I’m assuming I’ll marry and I wouldn’t trade her for anyone. But I’ll always have a crush on the memory of Karen.

— Edward F.

1. This is the story of two rejections. In both I was the rejector, so none of this was really all that painful for me, but still. When I was 23, I’d been dating a girl for five years. We were engaged and seniors in college. The plan was to get married a year after graduation but she already had her dress and a lot of the planning was complete. However, in the later years of our relationship we’d grown apart … romantically. Basically, she didn’t want to have sex, even though we’d already had sex. It got to the point where we barely even spent time together outside of meals and to go to the gym for a workout.

She was apparently fine with this, but I really wasn’t thrilled with a cold, non-physical relationship. To top it off, she decided that — months before graduation — she’d rather not be a teacher like she’d been working toward and spent close to $100K on at a private college. Instead she wanted to be a cop, which was completely out of left field and surprising since she’d made fun of her sister for throwing away her own expensive education to join the police force. Oh, and she was a triathlete, so all she really cared about was training and competition. I’m a slacker so that wasn’t a great mix.

Anyway, spring of senior year I went out to D.C. for a Model Arab League conference. (Think Model UN, only this was just a simulation of the Arab League. It’s pretty much all an excuse to get drunk and get laid for a week with people you’ll never see again.) I met a girl from a small, private, all girls college in the South and we hooked up. I didn’t call my girlfriend/fiancee for the whole week. When I got back, I gathered up all the crap she’d left in my room and went over to her place. I told her I’d been hooking up with another girl for a week, I didn’t love her anymore and that we needed to break up. She was pretty pissed. Again, she’d already bought a wedding dress and everything. So yeah, that was probably pretty painful.

After that, I started seeing another girl I went to school with. Frankly, she wasn’t very intelligent, but she was decent in bed. Unfortunately, she was also pretty crazy and started talking about our future kids and shit. We’d been together about 10 months when I’d had just about enough of it. As luck would have it, I was the best man in my buddy’s wedding and I met a bridesmaid (the cousin of the bride) at the rehearsal dinner. We hit it off, did some shameless flirting (my girlfriend wasn’t there) and had an instant connection. At the reception the next night we continued to flirt, but this time my girlfriend — feeling threatened and clearly territorial — was locked by my side the whole evening.

Both the bridesmaid and myself took full advantage of the open bar and toward the night’s end, we were plastered. I finally managed to get her alone of the dance floor and we ended up making out in front of everybody, my girlfriend included. My girlfriend lost it and when we got out into the hall just unloaded on me. I ignored her all the way back to the hotel, where she continued to scream at me while I pretended to sleep. The next day, after sleeping in, I went over to my girlfriend’s place, had make-up sex with her and then broke up with her immediately afterward. That was probably pretty painful, too, but I ended up marrying the bridesmaid, so it all worked out … for me at least.

I did get rejected myself once. It was in sixth grade when the girl I was “dating” had her friends break up with me on the playground after lunch. It was OK though, because she ended up having a moustache in high school.

—Jason, Wisconsin

Filed Under: Say What, Shane Ryan