@tooanxiousornot,
Quote:...he'd reimburse...feel awkward asking...
Just ask. Unless you want to send a message that you're willing to pay every time. Nip it in the bud. Likely he just forgot, doesn't mean you should not remind him.
Quote:...wine, flowers, toothbrush...
At least he's being good in this.
Quote:He pays for meals...ordered a sandwich...said "thank you" I assumed he expected me to pay, which I did.
If he is paying for food, then the sandwich was part of his debt. You made mistake by paying for it.
Anyway, for the future, remind him to pay when he says he will. If he doesn't, for any reason (says he forgot his wallet or something), press him. If he resists it may be best to move on.