My 29M BF I am 28F, he wants/needs a lot of reassurance from me, is this going to work out?

My BF29M is struggling with confidence and needing reassurance. I often tell him, I have told him he is handsome, great bf, that he is sweet. All of these sorts of things. Then he does stuff like after we went out to eat, he asked "Am I a good or bad boyfriend for taking you out to eat" then gives me a thumbs up or thumbs down. He does finger guns at me and he said, "Do you think I am awesome today?" He asked my ma (all at a fam event together) if I have dated many guys in the past, to which, my mom answered, "yes look at her, many men have wanted to date her" and he stomped his foot. Later he asked me for a number (I didn't count.) He asks me for selfies often and I am unsure whether he wants to see me or if he is asking to see where I am at.

I had someone close pass away and I was in a bad mental state, so I was on the Crisis Hotline. He asked to call, I said text only right now. He said, "that's super weird, you are being so weird why can't i just call? what are you doing?" I explained I am on the line with the crisis hot line. I told him the other day I am sad and unwell and he asked for a selfie, who wants to take a selfie during that?? He also reads all of my texts negatively, I say I am good, he says are you sure? You don't seem good. He also told me last week that he is continuing to date me past my red flags, and I said what are my red flags? He said sorry I love a lot about you. It's just the red flags my friends said, but I am patient and I am seeing it through. His friends told me being busy in life means I was seeing a lot of guys. I am not, I work full-time, I have a sport I am practicing, and I don't have excessive free time. I have not been seeing other guys. I never ask reassurance from him as long as things are good I feel that I know where I stand.

Also, does he trust me? Because he said he knows I am not a woman to be disloyal, but his actions say something else.