Back to dating and it never felt this confusing.

So, I'm 27 F and came out of a six year relationship 2 years ago. It took me all this time and covid to put myself out there again.

I come from Europe and maybe I was too young to know how dating really worked but I never thought multiple dating was a thing! And as someone who's introverted and always a little shy at first, OLD was my only option to meet new people. So, I went out with a couple of guys but never really felt that comfortable around them so after the first dates and some texting I dropped them, except this one guy.

Dating history: We matched back in May, we texted a little (I wasn't really interested) then he disappeared and texted back again after a month. On my own initiative, I asked him if he wanted to meet up since I was traveling to Florence (we live in the same region and it takes 1.5hrs from my place) and he said yes, and there I had my 'two night stand' at the end of July. It was fun and light and haven't had sex in a long time.

But T and I barely kept in touch and it was fine, I just wanted to be intimate with someone again and laugh. August was a busy month for him and I so we met again in September. I'm very reserved and he started talking about his family and asked about mine where I shared very little. I was caught off guard, let's say, and felt I wasn't ready to share personal information.

I asked him out again the week after and told him I got Friday and Saturday off and he asked me if I wanted to go somewhere and told him depends if he wants to hang out friday night or Saturday. Eventually he told me he'd be getting half day on Friday and spend time with me until Saturday afternoon before he travels to Milan to catch up with his friends. This particular weekend was when I actually started feeling something, like I want to really get to know this guy on a personal and emotional level and not just hook up. Also during this weekend I got random calls from my friends and after I got off the phone with them I asked him if he understood what I said (I was speaking Italian) and he said "yes, I can generally understand if someone speaks slowly but if they go fast I'm lost" and I jokingly said "lucky you I speak slowly" and his responded with "that's why I like you" I wasn't sure how to react so I just said "hah!"

Anyway, I saw him again and wanted to share my thoughts but it felt like it wasn't the right time and that same day my grandma went into coma so I was feeling weird...

Soooo, I don't know if I'm reading too much into this... I have no idea how to procede... Should I tell him that I like him or not and be chill about us... I also don't want to drive him away in case because I've never felt this comfortable, as in I am me and I don't need to impress someone.... I'm so afraid to expose myself and feel vulnerable...

Edit: I need to add that in those first two nights together he had problems getting it up for so long.. we both thought it was the alcohol bc we drank a lot in those nights and then on our next meeting it happened again and I thought maybe I was the problem but he said that it happened with someone else in August too bc he needs emotional connection

Submitted October 04, 2020 at 12:06AM

So, I'm 27 F and came out of a six year relationship 2 years ago. It took me all this time and covid to put myself out there again.I come from Europe and maybe I was too young to know how dating really worked but I never thought multiple dating was a thing! And as someone who's introverted and always a little shy at first, OLD was my only option to meet new people. So, I went out with a couple of guys but never really felt that comfortable around them so after the first dates and some texting I dropped them, except this one guy.Dating history: We matched back in May, we texted a little (I wasn't really interested) then he disappeared and texted back again after a month. On my own initiative, I asked him if he wanted to meet up since I was traveling to Florence (we live in the same region and it takes 1.5hrs from my place) and he said yes, and there I had my 'two night stand' at the end of July. It was fun and light and haven't had sex in a long time.But T and I barely kept in touch and it was fine, I just wanted to be intimate with someone again and laugh. August was a busy month for him and I so we met again in September. I'm very reserved and he started talking about his family and asked about mine where I shared very little. I was caught off guard, let's say, and felt I wasn't ready to share personal information.I asked him out again the week after and told him I got Friday and Saturday off and he asked me if I wanted to go somewhere and told him depends if he wants to hang out friday night or Saturday. Eventually he told me he'd be getting half day on Friday and spend time with me until Saturday afternoon before he travels to Milan to catch up with his friends. This particular weekend was when I actually started feeling something, like I want to really get to know this guy on a personal and emotional level and not just hook up. Also during this weekend I got random calls from my friends and after I got off the phone with them I asked him if he understood what I said (I was speaking Italian) and he said "yes, I can generally understand if someone speaks slowly but if they go fast I'm lost" and I jokingly said "lucky you I speak slowly" and his responded with "that's why I like you" I wasn't sure how to react so I just said "hah!"Anyway, I saw him again and wanted to share my thoughts but it felt like it wasn't the right time and that same day my grandma went into coma so I was feeling weird...Soooo, I don't know if I'm reading too much into this... I have no idea how to procede... Should I tell him that I like him or not and be chill about us... I also don't want to drive him away in case because I've never felt this comfortable, as in I am me and I don't need to impress someone.... I'm so afraid to expose myself and feel vulnerable...Edit: I need to add that in those first two nights together he had problems getting it up for so long.. we both thought it was the alcohol bc we drank a lot in those nights and then on our next meeting it happened again and I thought maybe I was the problem but he said that it happened with someone else in August too bc he needs emotional connection