Pussyblocked By Tom Waits!

We may earn a commission from links on this page.

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


I was about 20 years old and partying at the bars with my friends. I had just got dumped by this guy so was determined to get drunk, have fun and get laid. I live in a Canadian Navy town so it wasn't too much trouble if you really wanted to. Navy pukers are a dime a dozen around here.

I am at the bar in my best 1990 Le Chateau outfit and drunk. My sister is talking to the navy puker she is dating and there a bunch of his friends there. One of them, he refers to himself by all three of his names (which are Scottish and he has to keep saying them in a fake Scottish accent) is insanely cute and we start chatting, grinding on the dance floor, making out and having a good time. All his fellow navy pukers are cheering him on and high fiving and patting him on the back. He asks me if I want to go back to his place for coffee. I figure hey, why not?

I am thinking this is gonna be a good thing, but we have to walk to his place. Only about 15 mins so not bad, and okay if he doesn't want to pay for a cab. We have to walk through a group of prostitutes outside on his street. He says hi to them as he knows some of them by name, but I am so horny I am thinking no problem, what a nice guy. We walk to his rooming house, but I figure hey he's a navy puker so whatever. He takes me upstairs and makes me instant coffee by putting hot water from the tap on the coffee crystals, but I think how nice, at least he's trying. He shows me his room, which consists of a bare mattress on the floor, and I think no problem, at least it's clean. Let's get down to it.

He then proceeds to set the mood by putting on some music. What he chooses is Tom Waits. I wish I knew the song but all I can remember is it sounded like some awful violent serial killer movie death scene song, with all of the weirdness I associate with Tom Waits. He moved in and I was like, thanks for the coffee but got to go and pretty much ran out. Not sure why the Tom Waits creeped me out but there you are. No way was I sleeping with a guy while Tom Waits was playing. I was totally weirded out.

Ran into his friends at the bar the next week and they called him Blueballs. I felt bad, but there has to be something seriously wrong with a guy who chooses Tom Waits for his seduction music, amirite?


Yes you are.


During college I spent a semester abroad in Australia. I met "Sarah" at a bar crawl on Spring Break. Though we were in Brisbane at the time, it turned out that both of us attended the same uni in a suburb of Sydney, and even had a class together. We exchanged numbers and later went on an awkward "date" a few weeks later, which involved going to see X-Men with a group of my friends. Not even a kiss on the cheek at the end of the night. Total failure.

Fast forward to finals week, where there was a big party night at the one local bar that all the American students frequented. Not surprisingly, Sarah was there, getting obliterated like everyone else. I quickly caught up, thanks to Bundaberg, a rum & coke drink that is magically available on tap. The liquor must have fueled her libido, as she expressed a renewed romantic interest in me. Drunken conversation and dance floor grinding turned into heavy petting and a public makeout session.

We ended up back at her place, ramming our tongues down each other's throats. I was on my way to ending a cold streak, at least until a massive case of whiskey dick stunted any ability to perform. Not that she likely noticed, as she was close to passed out at this point. Undeterred, I excused myself and stumbled through her place, looking for a bathroom to empty my full bladder. In my drunken stupor I couldn't find a toilet, only a washroom with a shower and sink. It was tile, felt like a bathroom, and was good enough for me to urinate in the shower. I peed everywhere. I think I ran some water to clean up, but certainly not enough to cover my tracks. Piss drunk and full of shame, I staggered home.

The next morning I got a call from Sarah, asking if I had her keys. Sure enough, they were in my back pocket. I left them in the laundry room for her to collect, avoiding any additional embarrassment. Also in my pocket? Over $100, which definitely wasn't mine. Needless to say, I felt like a huge piece of shit at this point, having whiskey dick, pissing all over her shower, taking her keys and likely some money that she dropped on the ground. I didn't return the money. My friend convinced me to buy 3 pizzas instead. Finders keepers, I guess.



It was the week before I graduated college, during our school's senior week. I had been seeing a sophomore during the semester for casual flings, but because the academic year had ended, the only people left on campus were seniors. The relationship ended by default, she was back home and I was single.

The senior week event for that night was a pub crawl, and I participated to the fullest. The bars had the standard specials: $3 rails/$2 beers, etc and I took advantage of them, liberally. At one of the bars, I met my roommate, Pete, who was with his girl Caitlyn, and her housemate Samantha. Caitlyn wanted to go to bars in a different neighborhood, and I found no reason to disagree, so the five of us went to another bar and proceeded to order whiskey shots and mind-erasers. At this point I was sufficiently hammered and started to look and see what hook-up possibilities were at the bar. As this process was occurring, I engaged in a little flirtatious conversation with Caitlyn, who dared me to kiss her. In my drunken stupor, I leaned in to make a move, but Pete glanced over and basically shoved me off her. At this point, I had the equivalent of about 19 drinks, so I assume he was willing to let that move go due to my general intoxication.

About twenty minutes after this incident, we took a cab back to Caitlyn's house and sat down in her living room. Caitlyn brought out some popcorn, and with the effects of 19 drinks starting to hit me all at once, I vicariously downed it in an attempt to sober up. Caitlyn and Pete then retired for some sexy time, which left me and Samantha on the couch. I start to make out with her, and all is going well, but the little popcorn pieces are stuck in the back of my throat, which prompts me to break contact and to start coughing to try and dislodge them. Samantha joked at this point, "Maybe you should stick to only one pack a day" and I reply "I don't smoke, it's this stupid popcorn, Caitlyn..."
Samantha, having seen my incident at the bar, now finds the idea of hooking up with the guy who called her by her roommate's name unconscionable. I yelled "Caitlyn's roommate" in a vain attempt to finish the sentence, but that obviously didn't work. She slapped me across the face and yelled at me to leave the house. I complied, thus ending my collegiate romantic experience.

To make matters even better, I ran into her again while picking up my graduation robes. I didn't call her Caitlyn then.

In conclusion, fuck Orville Redenbacher.