Hmm... my wife usually stuttered like crazy and then just typed it backwards over msn or something. She says what helped her the most was that if I didn't want to answer she could just ask something else.

Also... maybe try other questions beforehand. Like work your way to it over time. Say like if you were curious if they liked X Y and Z ask them and gradually get more personal. Then when you do ask it shouldn't be as scary.

There's always telling him that you're scared he'll take what you're going to say to him the wrong way and prepare him so you'll be able to explain after you say it.