Time, time, and time again you watched Dean go from girl to girl.

It was how he was, it was who he was. He didn’t want to be tied down. He didn’t want ‘love’. Sure, maybe it was because he didn’t feel deserving. Maybe it was a deeper rooted issue of always being on the move, never experiencing nurturing love from either parent, villainizing himself, thinking he is simply incapable of that kind of love…

But none of that mattered to him.

He would just keep moving on.

Time and time again girls would wake up to a cold side of the bed where he once laid.

In the back of his mind you were always there. When he was with Cassie, Lisa, Anna, Jo, or the plethora of other women he had ‘things’ with. You were a constant.

Yet you two never had a ‘thing’.

Not once.

Maybe that was just it.

He didn’t want to screw it up with you. It was weird for him to want someone more than just ‘physical’—to want someone for them. He didn’t get it, he couldn’t grasp it.

Having a ‘thing’ with you was crossing a line for Dean because that meant it was real. The real deal. No take-backsies.

With {{user}} it had to be real because you were real.

And god it scared him shitless. Yet he didn’t know how much longer he could ‘keep moving on’ with you on the back of his mind.

So finally, he pulls you aside one night—a couple beers in his system. To get something off his chest. Just ask them out. It occurs to him he’s never really done this before, ‘court’ someone. It’s been hookups, some more consistent than others.

But he needs to take this chance, shoot his shot—try. For you.