I met a girl online and went to dinner with her, but she was so shy she hardly spoke. I tried to open her up by asking questions but she would respond with one word answers and did nothing to hold her end of the conversation. I'm not personally great at driving a conversation and am a bit introverted myself, but she was introverted to the max. I felt like a jerk but I decided to just finish dinner (which wasn't hard since we didn't waste any time talking), pay the check and get out.
Reminds me of a girl I saw in college. I had a new dorm roomate that year and we met these two girls who were best friends. After a short while of getting to know them he tactfully let me know that he really liked one of them. I was cool with that because the other one was super attractive. Probably the hottest girl I've ever dated. We all hung out a few times and then one weekend we all went to a party together. We danced and drank and had a lot of fun. Afterward we paired up and were making out. Everything was going great.
A weekend or so later, I ask her if she wants to go out to eat. A real date. My roomate and the girl he liked were really getting along great and I was excited that it was looking good with this girl.
Well we go out to eat and she just... didn't talk. I had to pry everything out of her. I'm a little awkward sometimes but I felt like I was annoying her by having to carry the conversation. I knew she was in the equestrian club so I tried to get her talking about horses. She talked for a few minutes and then nothing. It was like talking to a rock.
I tried real hard, mostly because she was gorgeous, but it just wasn't working. She knew it to and we broke it off. Felt like a missed opportunity, but our personalities just didn't work together even though we had fun getting drunk and hanging out together.
Sad part is, she ended up dating some frat douche and getting assaulted by him. Really messed her up and rightfully so. I felt terrible about it and tried to be a friend. Just sad.
Her best friend and my roommate ended up dating that whole year, even through the summer to the next school year. Then my roommate moved into the frat he pledged the previous year and dumped her. I don't know if that's a frat requirement or what.