So, Felicity Smoak is her name and she's adorably awkward, and that makes her incredibly approachable, whether she realizes it or not. Derek's adult relationships have been with women who were exuding confidence or bad assery. They all ended up being bad for him to some degree or another or, if not Derek, then the people he cared about the most. Meeting an attractive woman who isn't like that is kind of refreshing and reassuring in a way he can't quite put his finger on.

Derek goes for his morning run like he always does, because a change of scenery isn't going to change his routine, and this morning he decides to take a shower before he goes for coffee, specifically because he's meeting Felicity. It's probably the fastest shower he's ever taken and it's another quick run — jog, really — to get to the coffee shop.

As he walks in, he sees her and smiles to himself before making his way right up to her. "Morning. I wasn't sure you'd come," he admits a little sheepishly. The way he'd approached asking her was a little more humor-laced than he's usually used to doing these things and he wasn't sure she'd believe him. "I'm glad you did."