Why is initiating a kiss so difficult? I'm pretty extroverted but kissing some is so difficult for me on the first time. I need advice on when is the right time to go for a kiss.

So some background I just got out of 7 month relationship around spring break and I had kissed the girl, stayed the night, and had sex for my first time after just meeting in person. ( We had been talking 3 months before that as she lived in a different state up untill the point of meeting in person) she had been the one to initiate more in that starting part of the relationship. After meeting her I had no problem initiating sex, kissing, etc. As I am currently back in the dating scene and have gone out on a date with this awesome girl I can't seem to think of the right time to kiss her or anything. She seems to me at the very least to be very awkward. On our third date we went to watch firework at her campus and I had kept moving closer to her in the spot we had be sitting to attempt the very least to hold her hand or something ( I got the vibe that she was uncomfortable at least in the super crowded area.) So I waited till after when walking away from the area which we had decided to go back to her apartment (which was empty me and her only) on the way back I held out my hand to walk with her back there. Which she responded by stating that she noticed that I tried to hold her hand during the fireworks and said that she noticed the body language and I panicked a bit saying I didn't but was trying to be funny about it. She still ended up holding my hand. We got back to her appt and we watch a Monty Python and the Holy Grail and during the movie we cuddle on the couch. She got more into the cuddling and snuggled up to me. After the movie she drove me back to my car around 1 in the morning as there is no parking around her appt. When leaving I was hoping to get a hug or something more but she didn't get out of the car so I went for the awkward car hug. When I got back to my place after a hour drive I texted her and let her know I had a good time and she said she did too and my shoulder was comfy. Which I can only assume was a good thing. This week she is gone on a vacation so won't be able to to text her for about a week as her family is no phone on vacation.

I just want to know when the moment is right to kiss someone. I know i should just go for it but the awkwardness that I have experience is a bit much for me not in a bad way. Just need to know how to deal with something like this. I'm am terrible with the first initiating and I don't want to screw this up because I couldn't kiss someone. Or being seen as unmanly. I could use all the advice possible.

Submitted July 09, 2019 at 12:00AM

So some background I just got out of 7 month relationship around spring break and I had kissed the girl, stayed the night, and had sex for my first time after just meeting in person. ( We had been talking 3 months before that as she lived in a different state up untill the point of meeting in person) she had been the one to initiate more in that starting part of the relationship. After meeting her I had no problem initiating sex, kissing, etc. As I am currently back in the dating scene and have gone out on a date with this awesome girl I can't seem to think of the right time to kiss her or anything. She seems to me at the very least to be very awkward. On our third date we went to watch firework at her campus and I had kept moving closer to her in the spot we had be sitting to attempt the very least to hold her hand or something ( I got the vibe that she was uncomfortable at least in the super crowded area.) So I waited till after when walking away from the area which we had decided to go back to her apartment (which was empty me and her only) on the way back I held out my hand to walk with her back there. Which she responded by stating that she noticed that I tried to hold her hand during the fireworks and said that she noticed the body language and I panicked a bit saying I didn't but was trying to be funny about it. She still ended up holding my hand. We got back to her appt and we watch a Monty Python and the Holy Grail and during the movie we cuddle on the couch. She got more into the cuddling and snuggled up to me. After the movie she drove me back to my car around 1 in the morning as there is no parking around her appt. When leaving I was hoping to get a hug or something more but she didn't get out of the car so I went for the awkward car hug. When I got back to my place after a hour drive I texted her and let her know I had a good time and she said she did too and my shoulder was comfy. Which I can only assume was a good thing. This week she is gone on a vacation so won't be able to to text her for about a week as her family is no phone on vacation.I just want to know when the moment is right to kiss someone. I know i should just go for it but the awkwardness that I have experience is a bit much for me not in a bad way. Just need to know how to deal with something like this. I'm am terrible with the first initiating and I don't want to screw this up because I couldn't kiss someone. Or being seen as unmanly. I could use all the advice possible.