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Great Moments In Drunken Hookup Failure: Promise Rings, Triple C-Blocks, And Withering Rejections

Welcome to Great Moments in Drunken Hookup Failure, where we showcase six heartwarming true stories of drunken love gone horribly awry. Off we go.


This past Halloween, I'm getting ready to leave a party and head back to the apartment I'm just waiting for my roommate with his friend from home. It appeared I was going home empty handed when two girls come up and ask to start taking pictures with us. Five minutes and little bullshit later and we convince these girls to come back with us.

We get back and things are looking good I've know got a cute chick in a strawberry shortcake costume back in my bedroom. Were messing around and I see she's wearing a ring, playing around I ask her if she's married, she tells me no it's a promise her father.

I assumed she was kidding and played it off. So we're making out and after probably 30 minutes of her dry humping the shit out of me I try to get down to business but she's not having any of it. I go into my bag of tricks but I'm still coming up empty handed. She must have sensed I'm getting frustrated and tells me "I'm not gonna have sex with you." I asked why and she tells me THE PROMISE RING. Well, she ended up keeping her promise and I ended up with some serious blue balls and friction burns. Oh and her friend who was in the other room with my roommate's friend turned him down because her friend was a virgin and she didn't want to seem like a whore.


I'm all for purity, but that promise ring thing makes it seem like the girl, frankly, is married to her Dad. And that makes me terribly uncomfortable.

Then again, promise rings work?! I'm off to go buy my kid a promise ring.


I was with this girl I was going out with & her friends at a local bar in Santa Barbara & I happened to be in love with one of the waitresses & she was showing signs of warming up to me. The girl I was going out with left to give one of her drunk friends a ride home but was returning. I started to talk with one of her drunk friends that remained and before you know it we are making out right there at the bar. It was late and not too crowded so she grabs me by the hand & leads me into the woman's restroom where she proceeds to blow me in front of the sink.

I am looking at myself in the mirror watching the back of her head thinking how great this is when suddenly the door opens & there was the waitress I was in love with. She gasped in horror, blowjob ended & the girl I was going out with returned just in time to see me coming out of the woman's restroom with her friend. Triple blocked.




During my senior year of college, I had this huge crush on a friend of a friend. Lets call her Betty. Betty went to another school and occasionally came visit her high school friend to hang out and drink and what not. I would hang out with them and usually just end up gawking at her and making an ass out of myself because i didnt have the balls to ask her out. This probably went on for a good year. And then out of the blue, she actually asked me to her sorority semi-formal at her school, which was probably a good sign she was into me too. Score.

So on a Friday, the night before the semi-formal, i drove the 3 hours up to her school to party with Betty and her friends. We did dinner. We went to the bar. We went to a house party. And then around 3 or 4 am, we finally get back to her apartment. So now we're both beyond buzzed and we start hooking up. Betty becomes the aggressor and starts to go down on me. Nice.

Well a couple minutes later I hear her say . . . . "are you sleeping?" And thanks to an 8AM class, a 3 hour drive, and a plethora of beers, the truthful answer to that question was yes. Yes i was sleeping (beer #1 through beer #6? my energy increases linearly. Beer #7 and beyond? My sleepiness increases exponentially). Of course, thats not what I said. I cleverly responded with "ummmm . . . no", and she unsurprisingly didn't buy it and went to sleep herself. She wasn't offended enough to kick me out or ditch me as her date to the semi-formal the next night, but needless to say, that was the last action of a very awkward rest of the weekend.

Epilogue - over the last 5 years, I learned that my sleeping skills aren't just limited to oral pleasures, as I not once, but twice, fell asleep during sex (both times on bottom). Luckily it was with a long term girlfriend who knew my tendency to get sleepy during drunkiness, so she not only accepted it, but embraced it. So she let me sleep, and actually abused my body until she was properly satisfied, and then went to bed herself. Kudos to her.


Kudos indeed.


At a bar/music venue with some friends. Found a girl I was attracted to. Conversed for most of the evening. After about 3 hours of what I thought was flirtatious banter, I nonchalantly ask her if she wanted to go back to my place.

"Can two people fit under a rock?"

I slunk away with my pride somewhere around my ankles.

Oh, good God. That is brutal. People, if you have rejections in your life as brutal as this, send them in. You shouldn't have to keep that pain to yourself.


I once introduced myself to a girl in a bar and the girl laughed in my face. Just laughed right in my face. It was so horrible that even her friend came over and apologized to me for it. I then tried hooking up with HER. I failed.


A few summers ago, a buddy and I backpacked Europe for a month. This particular incident occurred in Prague. We went on a bar crawl, where you go to a few bars and then they dump you piss-drunk at some bar or another, in this case it's the basement of a larger bar.

My buddy and I met a pair of girls from Memphis, brunettes, and begin chatting them up. I have the better-looking of the two, who would actually be datable (if not for this story) and certainly worthy of a drunk hookup. Let's call her Maggie, which for all I remember could actually be her name.

Anyway, Maggie and I decide to go to the bathroom together, which means we walk around the corner from our friends and start making out on a bench. It's pretty intense for a bar makeout session, so I ask her if she wants to find a bathroom. We go upstairs where it's less crowded and Maggie goes into the ladies' room, checks to make sure nobody's in there, comes out and grabs me. Nice. We go into a stall and start going at it. Clothes start coming off, soon we're naked, I'm fingering her, about to go to town and she goes "Where's your condom?" FUCK.

We re-clothe and go join our friends. We have a couple more drinks and leave. It is decided that our two friends will go to our hostel, and Maggie and I will go to theirs. When we get there, some Aussies are drinking out back. She joins them for a minute while I go scouring the hostel for condoms. Success! I go back, get her to leave the Aussies and go back to her room. Well it turns out her room is one of those giant bunkrooms with like 100 people. Relatively luckily, she's on the top bunk in the corner. We get up there and I spend about 15 minutes rigging up the sheets as sort of curtains. I was proud of my work. We start going at it again. I go down on her for a while and I get the "kid-you're-in-the-game" tap on the shoulder. I roll over, pull out the condom, start putting it on, and she goes, "Wait, I can't." I go, "What do you mean?" She goes, "I have a boyfriend, and he's proposing when we get back." FUCK.


Oof. Double fail.


It was my freshman year of college, about a month into the school year. I had been talking to this girl. We danced for a while and then went outside. I sat down on a crate, and sat on my lap, and we made out for a while, with her grinding on my raging boner. Score!

After a little while, she asked me to walk her back to her room. The whole time, I am putting my hookup game face on. She clearly had a lot more experience than I did, and I wanted to make sure I didn't come off as bumbling or inexperienced. (After reading that, is it any wonder I didn't have much experience?) Anyway, I'm going over scenarios in my mind to make sure I didn't screw this up. I was focused. I was ready.

We arrived at the dorm and got in the elevator. She lived on the top floor, so she pressed the button and as soon as the doors closed, she got really close to me and whispered, "Have you ever wanted to do something kinky in an elevator?"

It took me off guard. I was still thinking about what was going to happen when we got to the room. I didn't have time to process the question or the implications of my answer. My basic instinct took over and I answered honestly. "No, not really."

She immediately slides away from me, and the gravity of my mistake hits me right in the chest. At that moment, we arrived at her floor and walked to her room. "Well, goodnight," she told me. My heart sunk while my balls ached. I talked my way into her room, hoping to get her back in the mood, but to no avail. We slept arm in arm, my boner pressing into her hip, but she spurned each of my advances. The next day, I took her to dinner, hoping to salvage something, but it was too late. I had lost all sex appeal to her. I learned a valuable lesson that day: When it comes to hookups, be prepared for anything she throws your way.



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