I live in the us and I can send pictures to people around here fine but I have a friend in canada that when I try it always fails I can send reguler text messages to him and he can send me picture messages and texts without any problems.

Any ideas why it won't work?

Probably a carrier thing. You might have to add international texting to your plan for MMS to work when sending to a foreign country.

Don't need to add International texting.

Most likely the carrier that the addressee uses doesn't allow MM or it is not set up on his account.

Have him check with his carrier.