Do I have any chance at a real thing/relationship with him?

I REALLY tried to keep this as short but many details feel relevant to me —— Known this guy for 6 years. Grew a bit closer in the past 3ish years. We used to text quite often but it was friendly, I knew I liked him but wasn’t sure what he wanted so didn’t wanna ruin it.
Texts fade gradually. Hang for the first time alone and drunkenly kiss in December (my bday).
Eventually we discussed it and came to the conclusion we’re both “into each other” but just wanna play it by ear. Comes over day after that convo, we have sex/talk for hours (July 17).
Still text once in a while and see each other out at a bar we frequent. Invite him over for birthday sex after the bar (April), sex/talk for hours.

This all seems applicable to my questions which are
1. If I lost weight would I have a better chance at dating him? Recently gained weight because of a med condition, which means I was smaller when we started texting a lot/bigger now. Need to loose weight for health reasons but I’m also wondering if it would help our situation or if I’m actually crazy? Looks mean a great deal to me.
2. Does this semi casual sex help or hurt the whole thing? As I said he knows I like him, says he feels the same (in so many words) so I’m not sure if this is a way of playing it casual/working towards something more or if I’m turning it into a friends with benefits thing (only happened twice).

Like I’ve known/liked him for a while and he’s really exactly what I look for, so I’m kinda looking for any advice that will help me win him over if possible. (Side notes: he always texts first, I brought up sex, I kissed him and don’t get a single fuckboi vibe from him [he plays D&D for gods sake] and when we do meet at bars we always seem to pair off from our group (s) and just talk to each other)
ANY ADVICE OR ANSWERS are appreciated. Or just tell me I’m hopelessly hopeless in this venture.
Do I have any chance at a real thing/relationship with him?
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