Jealousy is wearing me thin. Can’t tell if it’s warranted or not.

So my bf is naturally really social, personable, and friendly. But to a point that makes me uncomfortable at times. Like he will make small talk with strangers and has full-on conversations with wait staff.

He’s also been flirty with women in the past and hasn’t always been honest, so when I see him talk like that to women I don’t know, I get nervous. Usually I can hold it in, but for some reason, this interaction that was probably innocent, put me into a jealousy frenzy.

We were at a restaurant I really wanted to take him to. I was excited to share the experience with him. But when we got there, he turned his attention to the waitress and asked her what she recommended. Then they kept talking, asking where each other is from, etc. I felt left out after a certain point and got upset.

Usually I can hold it in, but I got so upset, I felt like I could cry. So I asked if we could get the food to go.

He got upset, understandably. I tried to explain myself and apologize. Usually he’s reassuring, but this time, he got extremely defensive and kept calling me insecure. I agreed, that yes I’m insecure and I admit I overreacted, but he kept on. Saying well, I guess I can’t even say hello to another woman, I might as well just never go out again, and other things of that nature.

I love him, but he has broken my trust before and rebuilding it has been hard. I know he’s trying, but seeing that was a setback and his reaction left a lot to be desired.

That said, to me, the defensiveness was alarming. Can’t tell if it’s just me being crazy, retroactive jealousy, or if it’s warranted.

Tldr; got jealous of bf making small talk with our waitress. Got so upset I asked to take the food to go. Apologized later, bf got extremely defensive. Alarm bells ringing in my head at his reaction. He has a sordid past as well, trusting him is hard. So can’t tell if I’m justifiably upset or unjustly jealous.