Overthinking ??? Help

Hi I’m in need of some advice, me and my boyfriend well we’re in between, I broke up with him because of an incident but now we’re building back up and taking it slow and we’re going to prom together ( I didn’t say I love you yet or kiss him yet I’m waiting and don’t wanna move fast) but sometimes I feel his personality is too nice, like whenever I ask him or we decide where we wanna go he’s like “ you decide I’ll be happy with whatever “, I have real love for him and sometimes I feel unsure but it’s natural and I’m young but should I talk to him about it? I know I sound so ungrateful but I researched this and it’s a real issue I wanna make this work, his family critiqued him saying “ she’s gonna break up with you” and stuff and I feel he’s insecure about messing up. I overthink constantly and I don’t know what to do. What do I do?