Boy trouble

So I just got back with my boyfriend like a year ago but before us obviously he had an ex, who he owes money to and still talk to because of it. But what i don’t get is why were they texting around 11 near almost midnight about money? When they had all day to focus the issue. Honestly I’ve been going through the motions & I don’t even know if to trust him anymore, cause of previous problems with his ex. Should I just end it? Or should I tell him what I feel?