<human>: Give me the gist of the text in a nutshell

Background: We dated for about 4 months 4 years ago. I (27F) started wanting more. He (27/M) did not. No hard feelings were had, just figured out we wanted different things.

In Between: We both entered into similar long term relationships. We each dated and lived with our ex for a little over 2 years. The 2 year relationships ended poorly for both of us.

Current: We recently found each other again. We have so much fun together! It seems like a great friendship again but when we do hang out we try to make it completely clear that we aren't trying to get into anything serious for a long time. We are both enjoying the shit out of our newly acquired independence.

We didn't have great communication in the past and I still have trouble with expressing my feelings around him. Our communication IS clear on what we want from each other, however. That has always been something we have been able to talk about seriously and agree on. A relationship is the opposite of what I need from him. However, a relationship is something I WANT from him. I think about him constantly and always think of things we can do together. We have been dating for about 4 months and I am terrified of repeating the history and losing him to the same "not being on the same page" shit.

The more I see him and spend time with him the more I want to be with him more seriously (i think?). How do I know when to move to the next step? How do you move from not wanting anything to wanting it all?

Side Note: He genuinely tells me he loves me when he's drunk...a lot. We never talk about feelings any other time.
<bot>: I want it, but I don't. He wants it, but he doesn't. How do you know when it's time to just say fuck it and go for it?