How can I help my boyfriend be less insecure?

As some of you may know, I have a boyfriend of nearly a year. Despite some differences (he’s filipino and 15 years my senior) we are happy together.

Lately though, his insecurity is annoying the crap out of me. I love him dearly but this is really starting to bug me.

Now let me just say, it’s not that he’s always jealous; that doesn’t happen that often (when he does get jealous, he’s not mad, just sort of sad.) Anyway, he’s mostly insecure about how he is in our relationship..is he good enough? smart enough? interesting enough? He worries that he won’t make me happy and I’ll leave and he’ll be heartbroken. He doesn’t worry about me cheating, just about me being bored with him, not loving him, and then leaving.

here are some things that he does..
1) He needs frequent reassurance that I love him.
2) He fishes for complements
3) He gripes about himself and his “many” faults
4) Sometimes, he won’t open up to me about certain things because he’s worried what I’ll think…I have to pry to get information.
5) He calls me a lot more than he used to.

I can tell he’s unhappy…there are some money issues, some family issues (sickness), etc. He’s under a ton of stress. I believe this may be in connection with him becoming insecure and needy, because he hasn’t always been this bad, esp with the calling.

How can I help him be less insecure? I’ve already approached him about this and he says that he’s just this way because of bad past relationships and that it won’t change overnight. :(