Not receiving pictures

I bought my boyfriend a new blackberry pearl 9100 this week he got it and connected it last night. I wanted to see if all features worked so I sent him photos and he never received them. This isn't the first time it happen even with his old phone he always had a hard time receiving. I had no issue getting his picture text. I think it might be an issue with the phone company he's with since I'm with bell and he's with telus. I never had issue with people not receiving my picture text.
I was wondering what could be the issue since sending photo takes almost 10 minutes till one of us receives it and also if I sent him picture text at night time after supper that's when he wont receive and ill try sending 5 times and by the 5 time it works.

a pic uses data, MMS so it could be the data plan

IDK if it's still the case, but in my older Pearl 8100, you had to enable WAP data push in order to get picture messages. Check that; I ran across it on the 9100 recently, but I don't remember exactly what menu it was in.