Supernatural – Image: SN09_MONDO_NM_ Jensen.0001 – Pictured: Jensen Ackles as Dean — Credit: Nino Mu–oz /The CW — © 2013 The CW Network. All Rights Reserved CHICAGO FIRE — Season: 4 — Pictured: Kara Killmer as Sylvie Brett — (Photo by: Chris Haston/NBC)
4. Dean Winchester (Supernatural) and Sylvie Brett (Chicago Fire)
Obviously, Dean Winchester’s most important relationship is with Sam. The closest thing to a romantic relationship he’s had came only when he thought Sam was dead. But heading into Supernatural‘s 13th season, a little love and a trip to Firehouse 51 might do Dean some good. Fresh off her breakup with Antonio Dawson, Sylvie Brett is ready to mingle. Given her past relationships, she tends to steer toward brooding but big-hearted jokesters, which at this point is a textbook definition of Dean Winchester. Having most recently dated a firefighter and a cop, it seems like a Hunter is the logical next step for Brett.
As far as Dean goes, the man has no clear type. But, some educated guesses can be made. Sylvie herself is a sweetheart, someone that would soften Dean up when needed. That said, she also takes zero flack from anyone, and would be able to challenge him in new ways. Of course, the biggest test of all is not just how she meshes with Dean, but with Sam too. When it comes to siblings, Sylvie has no trouble, seeing as Gabby Dawson (Antonio’s sister) continues to be her best friend, even post-breakup.
As an EMT, Sylvie doesn’t hesitate when it comes facing dangerous situations to save people, more than able to hold her own. With Dean being as protective as he is, having a girl as tough as Sylvie might relieve some of his worries. And really, given how often Dean gets stabbed, having a paramedic around would just be practical.