I've been spending time with this one amazing girl I met at school. We had kind of an awkward beginning because we're both kind of shy (especially her) with how to handle our feelings, but we've slowly been getting more comfortable with each other. I try really hard to take her on meaningful and carefully planned dates, and she's been super receptive to them. We've done quite a bit of cuddling, and she seems to enjoy getting as close as she can to me. The other day when we were out, she very shyly asked if she could give me a kiss. Of course I said yes, and we sort of cuddled up together when we did it. She had the biggest smile on her face after. We cuddled for a little while longer, and we kissed again. We spent the rest of the day cuddling and she'd very gently keep touching my shoulder or chest. Now, I think this went well. However, I sometimes struggle with confidence issues, and over-analyzing. I've really been trying to work on this, especially with her. She's gotten me out of my shell, and I've been taking the initative to ask her on real dates, not just asking her "wanna chill?" This was my first time kissing a girl, and she knows that. She's a bit more experienced than I am. Do you think she'll hold that against me? I don't think it was a bad kiss, it was fairly light, and I was trying to follow what she was doing. It actually wasn't what I thought it was going to be like. If it didn't live up to her expectations, will that ruin any chances of us having a relationship?