Ok, help needed please!

Ok, i know this mighe be quite long, but PLEASE read it, i really need some advice.
My best friend really really REALLY likes (maybe even loves) one of my mates, Bobby. And they have been out before, but it didnt work. Thing is, my best friend still likes him A LOT and im not sure if Bobby returns the feelings. I really want them to be able to go out cause i dont want to crush my best friends heart, cause i know this will.
Bobby is quite shallow, and always seems to want things he cant have.
please help me figure out a way to help bobby realize tht my best friend will be a great girlfriend :( i want her to be happy more than anything in the world.

please? :(

Well, maybe instead of directly saying GO OUT WITH MY FRIEND, imply it. Say, My friend looked soo good today. She's single, and her ex wants her back. Lol, It's confusing