He said what?!

I am not sure even how to preface the dating disaster story for this month, but lets just say I am happy this one did not happen to me.

My friend Tara, who lives up in LA, decided to get back into the dating scene after ending her three year relationship. She figured dating online would be a good way to get back out there and meet new people. She ended up meeting a guy who on paper seemed great. We will call him Tim. Tim was tall, good looking, had a job and didn’t live at his parent’s house.

Some how I think our standards for dating in the 21st century have gone down. But that is neither here nor there. 

So Tara and Tim made dinner plans to meet at a nice restaurant in Santa Monica. She was nervous, but when she got there everything seemed to be fine. He looked like his picture (always a plus when online dating) and he seemed nice enough from the first few minutes of their date.

But that is about where he lost her.

Tim then decided to start asking the hard, important questions most people ask on a first date with someone they have known all of five minutes, “What are your sexual fantasies? What are your fetishes?”

Yes, he thought this was appropriate conversation.

My friend Tara is definitely more on the modest, private side when it comes to things like this, so I can only imagine her face. Her eyes probably grew double in size with shock at his bold questions about her sex life. Clearly he was on this date for a different reason then she was.

She awkwardly said, “I don’t know.” He took that to mean she wanted to hear all about his fantasies and fetishes. So he proceeded to tell her some very interesting–and maybe disturbing scenarios–that he has tried or would like to try. If things went well, then maybe the next time it would be with her. Somehow she made it through a whole dinner with this guy only thinking about when she would be able to duck out.

Tim got up and excused himself to use the restroom. The older gentleman sitting next to them heard their whole conversation, leaned over and told her how he couldn’t believe this guy, and he said that she was too beautiful to be out with him.

Finally the bill came and Tara was able to finally leave the restaurant. If only her evening ended there.

The older gentleman from the table next to her chased her down Main Street, gave her his number, and told her to give him a call if she ever wanted to go on a date with a “real man” because she was a beautiful woman who deserved to be treated as such. The thought behind his gesture was sweet, but frankly he was way too old for her. Trying not to be rude she took the number and briskly walked to her car to get the hell out of there.

I am not sure what I would have done if I were in her situation. This is one of those dates that is so uncomfortable while it is happening but really does make for a great story later.

Have you ever had a date ask you very inappropriate questions on a first date that made you want to run out the door?


This article is part of a series known as Twenty-Something Dating Disaster Stories.