Love & Sex

Fifteen Courtship Blunders

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Our readers stand on the brink of eternal love, and screw everything up.

It was our third date, and I expected him to put out. We were talking on the couch, drinking a glass of wine, getting a little bit goofy. I told him that I was having a party, since my parents were going out of town, and I wanted him to come, even though I knew it was the same weekend he was turning twenty-two. He looked at me aghast and asked how I remembered his birthday. I leaned in towards his ear and whispered slowly, "I pay attention." He got freaked out, and we never hung out again. — Bonnie


The summer I was twenty, I went on a road trip with my friend Mark. I was painfully sexually frustrated, and it didn't help that it was summer, and we kept meeting all these beautiful, unattainable girls in every state in the union. 

Along the way, we stopped to hang out with a friend at Northwestern, and one of his friends was a cute girl with a literary streak. As we wandered the streets of Evanston drunk that night, she and I struck up a conversation about books; I lit up, since, as an English major, I knew that was one of the few subjects where I could really impress. Eventually, we started talking about Fitzgerald, and she asked, "Have you read Tender is the Night?" In an unthinking moment, I blurted, "No, but Mark has."

They ended up sleeping together. — Leonard


I was seeing this girl, and the relationship was developing in a very indie-movie kind of way. We met in a 3D-art class, and her opening line to me was "Do you want to come outside and help me burn things?" I was smitten.

Alas, two weeks in, and after three or four "seriously, it's time for you to put out" dates, all I'd gotten was a couple make-out sessions and a fleeting genital caress. Now, I'm all for romance, but I was starting to get a little fed up — I was putting out twenty-something levels of courtship for tween levels of affection.

So we were wandering the mall after seeing a movie, and I tried to put my arm around her waist as we strolled. She pulled away and said, "What are you, gay?" Now, that raised my ire considerably, given that I'd been dry-humping the shit out of her anytime we got horizontal on a couch, and so I said, "No, but you're definitely a bit of a prude." Which is when she told me she'd been assaulted. And… I'm the dick. That was pretty much the end of that particular romance. — Dave


In high school, I was walking with a friend in the evening, and we happened by the dorm where my biggest crush lived. Looking up, I saw her in the room; my heart swelled. In what I assumed would be considered a romantic gesture, I picked up a flower and threw it at her window. To make it fly, I also include a little clod of soil, which of course left a giant mud splat on the glass, as the flower drifted back down. Baffled, she looked out through her mud-covered window to see me grinning sheepishly up at her and my friend laughing at me in disbelief. She waved. — Jim


We were going to for a walk to this ice-cream place. Ice cream never really agrees with my stomach afterwards, but the girl I was dating really liked ice cream. So I took a regular laxative, thinking that it would ease the ice cream through my system. But I took it too early, and after we got the ice cream, my digestive system went nuts. On the walk home I was freaking out, and I tried to, well… you can just imagine. Also, I was wearing shorts. So I had this huge dilemma: do I hide it and act strange for the remaining twenty-minute walk? Or do I tell her? I told her. — Luke


I met this girl at a party. She was amazing, so pretty and smart, that it was intimidating. I worked up the nerve to ask her for her number, but was too shy to call her. A few weeks later, I ran into her at a concert, and pretended that I didn't remember her. It was the stupidest thing I could have done; later, I found out from a friend that she had liked me, and was hoping I'd call. I'd heard that feigning disinterest is a tactic, but I guess blatant rudeness is still unforgivable. — Patrick


I was dating this girl in high school who was a bit of a pothead. By "a bit," I mean stoned 24/7. But she was very sweet and very hot, if a little standoffish and aloof sometimes. Anyway, she'd smoked the last of her weed during lunch that day (ah, high school), and so by that night when we were hanging out, she was sober and pissed. Finally, she mock-exasperatedly yelled, "I just want some drugs!" — at which point seventeen-year-old me said, "You're my drug."

Now, I'd like to point out that this pre-dates Twilight, but it stands  as one of the few things I've ever regretted before I finished saying it. Needless to say, that cued up a devastatingly awkward silence that eventually suffocated our relationship and any hopes I had of her touching my penis again. — Andy


It's a rule: you're allowed to make fun of your own parents, race, or body type. But not other people's. This is a lesson I learned the hard way, when I re-told a racist (but I think kinda funny) joke to a young dark-skinned gentleman I was sort of falling in love with. [I won't repeat it, but it's the one from Boondock Saints]. Somehow, "I'm think you're beautiful," is sweet, and "I think you're beautiful; how could I be racist?" is uncomfortable. 

After that, we fizzled. Annoying, since I wasn't lying. He was beautiful. — Perry  


I was at a company picnic. I had just met this super-cute guy and was getting my flirt on when some brat threw a Frisbee at us. Instead of handing it to the child like a mature adult, I threw it with all my might into the nearby woods to get the mongrel away from us. "Kids are awful," I said, confident he would agree. "That was my niece," he replied. — Danielle


I was having a great drunken time with a girl I met at kickball; all signs were pointing to a splendid one-night stand. We got away from our teams and were at this sexy little speakeasy in the West Village. We were on the fourth round when I realized that somewhere along the way I had lost my wallet. The bill was like a hundred bucks. She sobered up real quick. — Scott


I had just started dating a girl I'd had a ridiculous crush on for years. I was also in the process of applying for work overseas, which involved a battery of STD tests. The morning after the first (and last) time we had sex, I heard back from my doctor that my tests were all clear. I sent her this text: "I just found out I don't have HIV or Syphilis. Whew!" I phrased it in that ridiculously insensitive way because, although I was not at all anxious about the tests, I thought it would be the height of comedy to suggest that I had been. Explanations, profuse apologies, and a few more dates followed, but that was the exact moment that I blew it. — David


Alex was a friend of a friend, whom I'd been idly pursuing for a while. One night, I met up with our group of friends, and we drank and then headed out dancing. At the bar, he and I found ourselves alone, and ended up making out for a minute on the dance floor. At the end of the night, he invited me back home "to watch Community and smoke some pot."

I'd been fighting off a cold, and had a pretty bad cough. In order to keep that from ruining our sexy time, I took two of the cough-suppressants that I was carrying around in my back pocket. Nyquil, it turned out, not Dayquil. A relevant fact when, after sipping them down with my fifth drink of the night, I passed the fuck out in the cab, my head on his shoulder. — Sam


We were holidaying in the Philippines. He was the perfect Aryan German; I was an infatuated Australian girl. During our first night together, at the hotel, a cockroach scuttled across the bed. I screamed! 

"Hush," he said, "If we turn off the lights and it will go away." Drunkenly, I responded, "Bullshit! Roaches can survive anything! They can survive a holocaust!"

"What did you say?" he asked venomously. 

I realized what I'd done. "No. No! I said a holocaust, not the Holocaust; there was more than one!" Affronted, he kicked me out of our room. Bewildered, I spent the night under a bar stool, cursing my idiocy. — Stephanie 


Early in college, I was on a date with an Icelandic girl. She was beautiful, buxom and blonde. We were walking through a high-end shopping mall, and I was amazed by the rail-thin, breastless models in all the windows. Without thinking, I said, "Wow, big boobs are really out of fashion." She turned, ample-bosom-ed as ever, and said, "What?" 

Here's where I should have just said, "Oh, I just meant the model's." Or "Never mind." Instead, I cleverly opted for, "Oh, not you, obviously — your breasts look great." I never found out if that was the case. — Kevin 


Aaron was a boy I'd been wanting all semester, a cute and sturdily built sophomore whom I somehow impressed enough one night to get back to my apartment. We were playing the "make small talk until we make out" game, when suddenly blood practically began to gush out of my nose. I rushed to the kitchen for a napkin to save my shirt and my couch. Obviously, it was too late for my dignity. I don't blame him for asking if I was in serious trouble and then getting out of there the moment I told him I was fine. — Colin