Lavigne and Sum 41’s Deryck Whibley seemed like the perfect punky couple. They had the funky hair, similar music style and were all over Hollywood together. So, it came to no surprise that the couple got engaged and married. Although Lavigne was very young, she sure knew a great looking diamond when she saw one. And Whibley didn’t disappoint. He proposed with a stunning 4-carat, cushion cut diamond, with a simple platinum band. The ring was traditional, much different than the image Lavigne fans had seen of her.
The pretty boy, and The Hills star has dated quite a slew of young pretty things. One even being, famous Playboy playmate Jayde Nicole. So when rumors started swirling that Jenner and Lavigne were…canoodling, nobody believed it. How did a famous tomboy met a pretty boy trust fund baby? Hollywood for ya.
