I'm recently single after a divorce. I started dating and matched with a great guy on a dating app. He had mentioned he hasn't had luck with dating in the past when we were texting. I asked him on a date and he agreed. We went to dinner and he told me this was his first date ever. He had been stood up and canceled on in the past so he just gave up. This didn't bother me but I did feel some pressure to make it a good date. He got uncomfortable when I paid for us and I simply said it's your first date so it's on me. We went to a play in the park after dinner and had a good time. He seemed to open up and be comfortable. I walked him to his car and he said he was nervous about this part. I was going to give him a good night kiss but decided of he was nervous it was better to not so he didn't feel pressure. A few weeks later we went tonthe fair and had a great time. Again I didn't kiss him because in my head this could be his first kiss and there just wasn't a moment that felt right. Like I want to make it special if it his first kiss. Am I over thinking that? I feel I need to ask him if he is OK with me kissing Him and give him the chance to say no. I know he is a virgin so thats a entirely different thought on my mind. As I plan dates I keep thinking back to high school and the classic dates. Things he may have missed out on. I should mention I'm the kind of person that likes doing nice things for others. Iv always planed things with others in mind. Making people happy makes me happy. I like this guy and his inexperience doesn't bother me i actually find it cute. He seems like a shy person but also opens up and tells me all kind of things. I feel comfortable talking to him about everything. I guess my question is do you think I'm handling this right and do you have any advice. I find my self thinking like I did in middle school when I started dating should I hold his hand, should I kiss him, does he like me, am I being to forward. This just seems like somthing kinda uncommon and any direction would be appreciated!