He plays a city boy on Gossip Girl, which is fitting 'cause in real-life Penn grew up in Baltimore and Seattle. So why will you and he click? You're both easygoing, active (Penn surfs, skis, and snowboards), and have a thing for the arts. For his part, Penn enjoys singing, writing music, and playing guitar. Yup, even though he comes off as elusive, this well-rounded babe is worth it!