Ross Gellar

Monica's older brother Ross has parlayed borderline "geek' tendencies into a career in paleontology (uh, that's dinosaur bones and stuff). Ross has quite a history with the ladies. He was married to Carol - a lesbian who gave birth to Ross's son Ben. Then he married Emily, a Brit who was completely jealous of Ross's relationship with Rachel.

In fact, after they were married, Ross realized his true feelings for Rachel and said "ta-ta" to Emily. Then he married Rachel, but that was a drunken, spontaneous Las Vegas thing, so it doesn't really count, right? What does count, however, is the time they secretly hooked-up which led to Rachel's pregnancy and the birth of their daughter, Emma. Now, Ross and Rachel are living together, but aren't dating each other. Could it BE more complicated?