I woke up with a German shepherd dog and a German Shepherd once, and couldn't remember why.
But seriously, my worst date was in university. The girl and I played pool (interesting comment...she missed a shot, and scratched her fingernails over the table, I laughed, she asked why, and I said I'd like those fingernails raked across my back, she smiled seductively) I fed her oysters (her first), she sat cross-legged on my kitchen counter while I whipped up a chocolate souflee (terribly distracting). We drank much wine, we talked, and as she was about to leave, we tried the 'European' kiss on both cheeks, but it ended up in some serious tongue action. I asked her to stay, she refused. We kind of lost touch after that. Why was it my worst date ever? Because I really cared about her.
The funniest date I had was in high school with a junior who looked like a freaking model. I was a senior. She took a pom pom and glued some paper eyes on it, and gave it to me as a gift. I had to date her. So, I took her out for a very expensive dinner, and sat next to her at the table. The waiter came by and suggested we sit across from each other, as it would be more 'aesthetic.' Anyway, we went back to her place (I was pretty shy at the time) and watched some TV. Eventually, I gathered up the courage to put my arm around her, kiss her, spread my legs all over her (oh, the ecstasy of groping) and then her mom came home and ruined the show.
I also have a vomit story, although Bear's are probably better.
In university, I was always the friend, rarely the boyfriend. The first girl I met there was beautiful, and I maintain to this day that we were in love, but we were both too shy to do anything about it. Anyway, we spent the night together platonically TWICE. The first time, we watched 'Withnail and I' and drank a lot of vodka. Things were actually looking really good....and then....something rumbled, and I had to puke. Thankfully, I made it to the bathroom. She had a spare toothbrush...After I cleaned myself up, she held my head, coddled me, and then changed for bed. Just before I passed out on the couch, she came to say goodnight in a beautiful nightgown. Hmm...maybe that was one of my best dates.
The second time we spent the night together, we rented some cool videos, and picked up some beer. When we finally decided to call it a night, we were lying on the floor together, laughing and talking, both wearing black pants and black t-shirts. That's when the boyfriend showed up, pissed off as hell. She took him into the bathroom and closed the door. I could hear the conversation. She completely harangued him, and he went on his merry way. I spent the night on the floor, listening to her cry, and making the best attempt to console her in her misery. Yet, I lacked the confidence to parlay this into a relationship. Poo on me.
I was never a good dater.
Then there was the time I banged my ex's best friend, but that was good, not the worst by a long shot, heh heh.