Jenner, 28, is a self-described "hilarious smarty-pants" who'll do anything for a laugh. She works in real estate; loves sports, kids, and guys with tats; and has a thing for Nick Lachey. Her perfect mate? A man with a sense of humor who loves his mom but puts the focus on her.
Here are the guys we set her up with. Can you tell which one's gay, which is straight and which is taken? Find out Monday, February 12 at 8:30 pm et/pt!