I want to break the curse...

I've been talking to this boy for a little over 7 months now. We're not in an relationship with lables yet because he's afraid to put trust in me. This is because his exs emotionally broke him so severely. We were on the phone last night and he mentioned that he hated valentine's day. I asked why and he said it's because his ex broke up with him the day before and for that he holds a grudge over that day. This really bummed me out because this will be my first time actually celebrating valentine's day with someone and it's already ruined by something I didn't even do but I'm not settling for that. I see he has a hard time letting go of his past because he's been hurt so many times by people he thought he could trust (explains his trust issues) and because of that I have to deal with the aftermath of their actions. I know there's a lot to his healing process but I want to start off by making Valentine's Day happy again for him by making him feel special. I've already decided on one of my gifts for him and that is a series of "open when.." letters (letters written to be opened when the receiver is feeling some type of way throughout the day happy, frustrated,etc.) Though it may seem like a bit much considering we're not an actual couple yet, I wanted to do it for reasons beyond us. I want him to see the brighter side of things and finally let go of his past so he can live better and happier. I want to do more things for him but Im stuck on ideas. Any suggestions? (P.S: I can't drive and have a curfew of 11pm so not all ideas may be suitable for me lol)