Caroline and Zach
- Her: Caroline from The Vampire Diaries
- Him: Zach from The Crazy Ones
- Why they'd work: Caroline is in an adventurous phase of her love life now that she's single, and she needs a fun guy who knows how to treat ladies but won't get too attached. As for Zach? He's dated every kind of lady, but we doubt he's gone out with a vampire yet.