This goes to the guys who aren't exactly the casanova type. Have you ever had a goal of dating a girl who you believe is out of your league and succeeded? How was it? The most I ever got was going out with this girl I had a major crush on but it wasn't a date cause it was just helping her with school stuff. Back then I was too afraid to actually ask her out, which was lucky cause I realized we barely had anything in common. I was just attracted to her beauty and bubbly personality.