I have had a few.
The most notable one would have to be this girl i was dating in high school. We were pretty serious and it was getting toward the end of my senior year and she was going schizo about Prom. I asked her and she said yes. So being a working guy (Having a job at 17 working 12 hour shifts graves) I paid for everything because i had a bit of disposable income.
She shows up and asks if she and her 'friend' (a gentleman i haven't met before and knew nothing about) could use my bathroom to get ready.
Of course i say "you can, he cannot, as i don't know him"
She responds with random anger and storms into the bathroom, after trying to stealthily grope him, not realizing from that angle i missed... NOTHING. He sits on my couch and glares at me for the entire time, whipping a butterfly knife in and out, trying to intimidate while i sat in my chair, doing nothing really. (Besides texting my best friend, and requesting him to get over to my house)
She returns, 'ready' for prom. Picture this if you will:
I spent probably 200 bucks on her dress and shoes and accessories. It was a rental but i paid for the insurance and whatnot. She picked out the dress and everything and i merely paid for it.
Instead of using the hair straightener on her hair, she decided to burn holes in said dress. She had shredded the wonderfully crafted lower part til it looked like a cyberpunk fairy from a 90's cartoon show would wear.
She then rips the dress off, tells me i'm a selfish asshole, gives the random guy the sloppiest, most oddly sexual kiss right on my couch and they laugh and leave.
(I was able to return the dress and after apologizing profusely and telling the guy i'd pay full damages, he didn't charge me full price {400 extra dollars}. I managed to only have to pay an extra 100)
So yeah, my net profit for that 'date' was a ripped up dress, a trashed bathroom and a rather psychotic ex girlfriend, who i STILL, don't have any idea how i managed that one.
My buddy showed up, and we went bowling instead. He was such an awesome bro, he had a tux left over from a wedding and since i was mostly gussied up, we went bowling in tux's and ties. Probably the most fun I've had bowling ever.