Just recently, I was rejected by a girl I work with. She's 18 and asked for my number because I'm older and she thought I'm cute. So, over the past couple months, we went out on three dates. First date was a walk on the beach on a nice sunny day. It didn't go great, but not bad either. It's just I didn't have much to say because of the shyness. I was nervous about running out of things to say, so I looked up questions to ask on dates beforehand. There were still a few silences and the conversation didn't flow that well. Yet, we still went out again, next time to a drive-in, which she suggested. Of course, this probably means she was hoping I get a little physical and kiss her, but I didn't, and I regret that. We only cuddled. I think this was my first crucial mistake because she sensed a lack of confidence after that for not going for the kiss. Hell, I haven't even kissed a girl yet ever and I'm 23-years-old so of course I was nervous. I just wish I would've went for it so I could finally get my first kiss. Anyway, after that she started showing less interest, and, after I asked her out again, said she couldn't hang out for three weeks because she was going out of town. I played it cool until she asked me out for a drink after work. I blew it here. I don't have much experience flirting with and teasing woman, but I tried, and unintentionally insulted her instead. Me: "I like your nails" Her: "Thanks. They were done badly." Me: "Because you did them?" Then, after I stroked her hair telling her how soft it was because I wanted to kiss her and make up for last date, she said she had to get going right away and offered me a hug. Her: "I just hope I don't annoy you at work." Me: "You just get in my way sometimes, but not in a bad way. You can't help it." Yep, I shot myself in the foot. She doesn't want anything to do with me now, especially since our work situation has been awkward. I'm shy at work so I don't talk to her other than saying "Hi" or "Hey, how are you?" and that's it. I've also showed a lack of confidence and shyness so I think she's completely turned off now. It sucks because I thought this could have turned out to be something really good in my life. She's one of the most beautiful woman I've ever laid eyes on, not kidding. And, she asked for my number and was initiating texts with me at first! Yet, I blew this opportunity. *facepalm* 23-years-olds and still never had a girlfriend or a kiss. But, on the positive side, at least I got some experience and this did motivate me to start a journey of self-improvement. I want to be ready next time. This came out of nowhere. I mean, what girl asks a guy for his number before they've even talked to each other?