PopWatch Matchmaker: Dean Winchester and Laurel Lance

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Image Credit: Cate Cameron/The CW; Sergei Bachlakov/The CW

Some of our favorite TV characters are often unlucky in love. They just can’t seem to find The One — but what if The One is on another show altogether?

Disclaimer: I know Katie Cassidy already played Ruby on Supernatural, so suspend a little disbelief here and focus on characters, not appearance. Or perhaps, Ruby’s vessel was Laurel Lance. (Did your head just explode?)

Laurel Lance … where do I begin? In season 1 of Arrow, Laurel was presented as the strong female. She had survived the death of her sister, her mother’s leaving, and the return of her ex-boyfriend (who had cheated on her with her now-thought-to-be-dead sister). After all that, she was still kicking. She was working her way up in the world of law while simultaneously taking care of her heartbroken father, not to mention that she was a class act when her ex, Mr. Oliver Queen, returned from the island. But now, one year later, Laurel has just about done a 180. Yes, I know she lost her boyfriend in last season’s finale, but so far, I feel like every single time she’s on screen, it’s a pity party.

Quite frankly, I wanted Laurel with Oliver last season, but now, I don’t see them working the same way. I think Oliver and Felicity have a lot more chemistry, and I think Laurel needs to do a little soul searching to figure out what she wants. To me, the girl doesn’t seem very happy with her life as a whole right about now. What she needs is to hit the road and find a man who won’t let her wallow in self-pity anymore. Enter Supernatural‘s Dean Winchester.

Now, I know that Dean is also in a very dark place right now, so he isn’t necessarily the perfect partner. He just lost his brother to an angel and more than likely blames himself for the death of Kevin Tran. But if I know Dean, he will keep pushing forward. The man has literally been through Hell (and purgatory), and he still knows how to enjoy himself (when his brother isn’t being kidnapped). But that’s only one reason why he would be a good match for Laurel.

I know what you all are thinking: The Winchester brothers have tried the relationship thing, and it never works. Not only do they live very dangerous lives, but they live on the road. However, I could argue that the reason they never find a relationship that works is because they pair up with women who are settled in one location. For example, Lisa had Ben, which meant she couldn’t adapt to Dean’s lifestyle, and we all saw what happened when he tried to adapt to hers. But Laurel doesn’t have anything holding her in Starling City. Sure, her dad and her job are there, but they’re not going anywhere. And considering that she hasn’t done a whole heck of a lot so far this season, what would be better for her than a soul-searching road trip with a super hot lover?

I’m not saying that Laurel and Dean are made for each other, but I think they could help each other through some tough stuff. They could cry together, and then hit the road and have some (probably dangerous) fun. We know Laurel likes strong, handsome men, and we know that Dean likes equally strong, beautiful women. It works. Plus, it definitely wouldn’t hurt the Winchesters to have an attorney along for the ride. Plus-plus, we’ve all seen Laurel kick some butt. I wouldn’t exactly be worried about her safety.

So here’s what I’m thinking: Laurel decides to take her pity party to a bar outside of town one night. She’s drinking alone when Dean enters. He’s doing his usual — hustling some guys at the pool table — when Laurel catches on. As an attorney (who perhaps has had one too many), she walks over and whispers that she should report him.

Dean: “But you won’t.”
Laurel: “And what makes you so sure?”
Dean: “Because then your night would be ruined.”
Laurel: “Excuse –“
Dean: “See, if you report me, I’ll have to leave this bar, which means you’ll be left with all these nice folks.”

They both glance around at the older, slightly rough crowd of men occupying the bar.

Dean: “Now, something tells me they’re not your type. Am I wrong?”
Laurel: “You’re wrong in assuming that I came here looking for someone.”
Dean: “I didn’t say you came here looking. I’m just saying that now, you’ve found someone.”

They both smile at each other before a man walks up and grabs Laurel’s ass. Dean goes to hit him, but Laurel beats him to the punch. Shocked and turned on, Dean asks if she wants to get out of there. She agrees. You can figure out the rest.

The next morning, over breakfast, they don’t quite exchange sob stories, but they both sense a sadness in the other. Laurel decides then and there that a road trip is just what she needs. Dean takes some convincing — he’s not quite ready to explain the monster thing to her just yet — but when she threatens to follow him until she has reason to take legal action, he decides having someone in the passenger seat might be nice (until Sam gets back, when she will likely move to the backseat).

Just like that, they hit the road.

Bonus: This could potentially lead to shirtless mud wrestling between Oliver Queen and Dean Winchester! Too far?

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