Care to help my friend?

My friend is one of those few people who suck at dating and he asked for advise the other day about my friend Jessica. Now he asked me how to approach her and ask her on a date, I kept saying just go for it but he refused and was being a stubborn mule about things and insisting that it wouldn’t work if he did that. So when I pulled out my iPhone to check my fluther status, he asked what it was and wanted to know if I would ask the collective. So here I am a day later being the middle man, please be nice to him, I’m printing this page out so he can read everything for himself.