Reuben is Gibby's best friend, who had an unrequited crush on Sam. He speaks in strange metaphors that no one, except Gibby, can understand. He stopped liking Sam after she used a strange metaphor that apparently insulted him. Though Sam didn't even understand what she was saying, she was glad to have said it.
Reuben only has one line that can be understood completely by people other than Gibby; when Sam tells him, "I'm sitting here eating cheesecake with an Australian Eskimo who's got ointment all over his bumbleberry!", he cries, "Oh I can't believe you just said that to me!" and runs away. He only appears in iWin a Date.
In one of Sam's blogs, several of Reuben's metaphors were explained:
Hello. How are you today?
'Sup soda bottle nose. Are your roosters dancin'?
I'm fine. Thank you. You can't drink two jars of applesauce if you don't lift the guard dog.
I think you are cute.
Wow, you can make a dog bark faster than a fish can climb a tree.
I think you're gross.
You've got ointment all over your bumbleberry.
I can't finish this enormous piece of cheesecake.
Ya might as well tie a knot around two kangaroos, know what I'm saying?
Does a six-finger chimpanzee eat cardboard nuggets for breakfast?
Does neon spaghetti take a sandwich ride down to the polo field?
I ate too much.
Ugh, I've got more pigs in a blanket than hobos have sideburns.
I would like to go on a double date with you and your friend.
I'm ready to hang my socks on the monkey parade.
Please, calm down.
You don't need bubble-wrap to know when it's chowder time.
See ya at the ketchup factory, Bubbleface.
There's my girlfriend!
There's my raspberry soccer ball!