I'm not sure you need to elaborate, but if you want to, I'm certainly happy to listen. Context is always important.

But the reason I said you probably don't need to elaborate, is because sometimes even little bits of information are more than enough to be able to provide a logical conclusion. Let's start with the break up. It was because he displayed controlling behaviors. Are those behaviors now gone? If not, nothing else matters and this needs to end for good on that alone.

Now let's talk about "I've been questioning my relationship for a while now." Why? You then say that you've now started "truly" worrying, but if you're honest with yourself, you've likely always been looking for something "more" to do what you've already known you should have done. I'll get into that next, but just know that to make a statement like that, there's a reason for it, and it's a big deal.

Let's then discuss the friend. How did he meet the friend? To back up, I'm the first person to come on here and say that opposite sex platonic friendships can be perfectly fine, but like anything else, context is everything. So again, how'd he meet her? It's certainly odd that he'd then be going on a trip with her, let alone a family one, this soon. His double standard should also be a deal breaker, so there's that.

Finally, his behavior. Have you seen him since? You only mention his behavior initially. You have every right to be upset by that, but was this today?

Regardless, I think you've always questioned how happy you are, because you've largely not be truly happy. You probably think you have been, but you've always had reason to question things. The likely advice is to run and never look back. But if you want to provide more context and answer these questions, we can go from there.