Don’t think about Cas sitting somewhere by himself on a college campus just reading a book and Dean and a group of his friends walk by and Dean is just like,
“I bet I could get his number and a date in less than a minute.” And his friends are like, “haha, yeah right. He’s out of your league, Winchester. Novak’s don’t date. They just curve all the tests.” Then Dean goes, “I bet you $200 each. And I’ll even add in an extra bet that I’ll get HIM to kiss ME.”
So they take the bet and Dean just waltz over and sits down next to Cas and just smiles at him and says, “hey, sweetheart” then hands him his phone.
Seconds later Castiel just leans forward and kisses Dean on the lips and goes, “are you scamming your friends out of money with bets again? You know eventually they’ll figure out we’ve been dating for a little while.”
Then Dean just grins like, “And that’s when I’ll stop.”
Meanwhile Dean’s friends are just standing there in shock because what did they just see?