Will it turn out this way

So to begin I have this friend that I have known for 7 years now him and I dated once back in year 6 then again in year 8 or year 9. He moved and I only moved to the same city as him two years later and between those two years we didn't chat at all even though before we chatted every hour.

Now fast forward to last year and this year and we start to hangout and talk every few months, getting out of a relationship a few years before this and as we start to talk recently I see how much we have in common and how much I have missed him, he even gives off this flirty kind of humour and I'm kinda scared that we might date again if we hangout this year but I'm not sure if I want to or not and if he asks me I'm afraid I might say no even if I want to say yes. Thing is he says things that can come of weird and creepy so I brush it off since usually he is funny and we just get along, I don't know my question is how will I know what I want to happen without regretting my decision after.

I love him and I care about him a lot but I don't know if I will ever be ready to date him again but i don't want to be alone anymore.