Responses
#2 sounds like https://www.mangago.me/read-manga/dream_away/
#1 sounds similar to this?
https://www.mangago.me/read-manga/green_apple_paradise/
I think they're the right ones. Thanks guys.
1. MC had a secret crush in High School but surprisingly met his crush again in college. He also becomes a money-spender when drunk, I believe.
2. MC can predict the future, I believe through dreams, and creates a misunderstanding thanks to a car accident the he had a vision of, making the lead think MC is actually trying to flirt, rather than prevent the car accident.