Kara invites her bestie name twin Kara Wassman on the show to discuss dating disasters. Winslow has been single her entire life. Wassman is back on the dating scene after a recent divorce as a mom of two. What's like to be middle aged trying to date in a college town. Winslow always ends up with crazy ones. Wassman with the Eeyores. Maybe one day they will figure out how to navigate the ways of dating and relationships For all the latest contests and h...