Bad Date Stories
Spying Yuppie / Prostate man

After a more than bad dating experience with a young man 5 years my junior, okay, more than dating, it was a 6 month relationship, my friends suggested a try to date older, more mature men. I learnt never to take the advice from friends on dating again.

I met a yuppie, around 5 years older than I who had his own business. He seemed nice enough. Mature, no room mates and a cat. He was quite the opposite from my previous experience. I’m not sure about a single man who lives alone with a cat. It just doesn’t seem right. He was far from cute. Rather icky actually, but I thought my friends might know something I didn’t. We went out a few times for dinner. He told me about his prostate problem, which seemed to cause him to not be able to get an erection. He hadn’t been laid in years.  I don’t know a thing about prostates, and I really didn’t need to know that much about him after only a couple of dinner dates.

We had dinner one night. Conversation was just not interesting me once again, so when he wanted to go somewhere after our meal, I said I really had to get home. He dropped me off. I went up to my apartment, put my ‘club’ clothes on and walked to the bar across the street. The next day the bad date called to tell me he saw me go to the bar after he dropped me off. What the heck was he doing outside my apartment for so long? I didn’t go out for at least 15 minutes after he dropped me off. The guy was watching my apartment.

You would think that would be the end of the tale wouldn’t you?

I was having drinks with a female friend in town. Prostate Man called me on my cell and asked where I was. I told him. Big mistake! He showed up. We all chatted for a while. He was a little jealous of the hockey team talking to my friend and I. To ease the situation, the three of us decided to head to another bar where PM’s friends were. A group outing seemed okay. After a few martinis, PM’s friends wanted to head to another bar. My gal friend and I said we would meet up with the guys at the next bar a little later in the evening. We took a detour to the next bar, by dropping by the bar we started at. Getting confused yet? Not two minutes after we walked into our original bar, PM showed up and started yelling at me. How dare I make a detour he was shouting. Geez, it isn’t as though we said we would meet them right away. He hadn’t even gone to the next bar. He either followed us or just knew where I was going and wanted to cause a scene. The guy was scaring me. I hid in the bathroom. He waited outside. I eventually came out. He started yelling at me some more. I hid in the bathroom again. He waited for half an hour outside of the ladies bathroom before finally going home. He then proceeded to page me every 5 minutes for the rest of the night. I was scared to go home. He continued to call me all the next day and e-mailed me for weeks. Eventually he gave up and I finally felt safe going home at night. This yuppie, thirty something, business owning, prostate man was a date from hell!

~annonymous, November 2000

send this to a friend

Submit a Bad Date story here
Current Bad Date stories

previous bad date         list of bad dates         next bad date