An update:
We spent a total of 7 hours in a car together because he was nice and drove me to visit my friend on his way home for the weekend and the trip there we were mostly listening to music and joking around and I met his family briefly before my friend picked me up. Didn't hear from him the whole weekend but I assumed that's because he wanted to let me enjoy time with my friends.
However on car ride back, we both got into deep conversations about situations with old ex friends and then ex partners. He finally opened up about his ex to me and I did the same. How did I feel about that? I felt like I was 'getting closer' to him and how he's a great friend and I even mentioned that to him and he agreed and said how he wished we met earlier.
However in talking about his ex I know she still has an emotional hold over him. I think although he says he's moving on, he's not over the relationship fully and even disclosed he would be upset if she were with a guy and she would flip if he started seeing people but he said he's ready to... hah not quite sure about that.
After the car ride we came back and I noticed that he started joking around with me a lot more. Like teasing me and throwing snow balls at me... and then we went to grab dinner together... and I'm happy to say I'm content where we are at... no rush.
:)

