Ryan Cabrera close relationship with the entire Simpson family has only continued to grow over the past year. He’s dated Ashlee Simpson on and off, toured with Jessica Simpson, and is managed by Joe Simpson. In an interview with frontrowfanz.com, he becomes serious and genuinely sincere as he talked about the family and their support. “They have all helped me in ways I never could have imagined.” But, Ryan stopped to laugh and recalls an embarrassing moment he had with the family, mentioning that even he makes mistakes. “Just recently, I was backing out of the driveway and suddenly I hear this crash,” he revealed. “I look back only to realize I had hit Jessica Simpson’s brand new Mercedes Benz. I considered just driving away, but then her car alarm went off and the whole family came running.” He felt terrible and admitted he was almost in tears. But to his relief, Jessica didn’t make a big deal about the wreck and said she didn’t like the car anyway.