Bottling feelings up

Samantha • Ohana means family and family means no one gets left behind or forgotten.
So me and my boyfriend have been with each other for a year and 8 months (nearly 9) and a lot of the time I make the effort to do things together and things like that. He isn't completely useless, he does think of things maybe sometimes. I know he loves me and I know he has feelings for me and I know he wouldn't know what to do without me before anyone thinks he is useless because he isn't. But I feel as though he is bottling things up and won't say to me and I feel sorry for him sometimes like that. Every idea is there to be nice to do different things, it's just he doesn't do them and I ask him why and he will say he doesn't know. I don't know if he is to shy or may feel silly I don't know. If the idea is there then why won't he show that? He has never been in a serious relationship in the past because girls have always messed him around and it takes him time to show his feelings deep sometimes and I try and help him out so he can be more open as he has never had to be. He tells me more than his own family and I feel happy to know he can. I don't know what it could be? 
We're also getting engaged at Christmas so I'll be curious as to how he sets it all up ( all suprises )