He is not obsessed, thankyouverymuch.
Okay, yeah, sometimes starting to border on often he gets himself off (in bed, in the shower, during Mad Men for some reason) while imagining what she'd be like if he pushed the right button.
(Abed once said something about Annie's face. Was it tracing her cheekbone with his fingertips? Brushing her hair off her forehead? Lifting her chin with his fingers? Wait. How does Abed even know that about Annie?)
Then again, Britta has featured in quite a few of his X-rated fantasies over the years (it helps he's got some real-life experience). So has Shirley (sssshhhh, don't tell Shirley).
(Sue him. He's a straight guy and they're all beautiful women, okay?)
The problem isn't just that the Annie fantasies have started becoming his go-to; they've also taken a disturbing turn. The fall of thick, dark hair. The dark red lipstick. The knowing look underneath lowered lashes. The dirty talk whispered through a Disney princess smile. The darker colors of her usual girly fashion choices.
He totally blames Britta for this.
(Why not? She's the one that told him about the darkest timeline.)
Annie — real Annie — would finally snap and gut him alive she ever knew about his messed up fantasies. It wouldn't even be the messed up part that would lead to his execution, it's the fact he has any fantasies about her at all. Because he swore up and down, and denied, denied, denied that there was anything whatsoever going on his end and that everything was all in her head.
It's always been grow up, Annie and it's just a crush, Annie and you once were all about Troy, Annie in a constant string of no-no-bad-girl that got dumped on her shoulders while he skated away mostly scott-free.
For that alone Annie would cheerfully murder him. Britta would help her hide the body out of sisterhood solidarity.
At least Shirley would pray for his soul, provided she didn't find out about those few times he imagined Shirley riding him hard and promising him an unending supply of brownies that would never make him fat.
(Seriously. He wonders about his lizard brain sometimes.)
But in all honesty, the problem isn't the fantasies (it's not, it's really not). He can handle the fantasies and lock them away so no one ever knows. It's reality that's becoming a bit of a problem.
Annie has added a black cardigan to her regular wardrobe. And she just as often has taken to wearing dark red lipstick, alternating with the flavored lip gloss. He doesn't even want to get into whatever it is she's started doing with her hair. He really, really doesn't.
And when she sometimes catches him staring at her (in confusion, in the shock of recognition, in simple want) she shoots him a confused glance.
He always responds with a sarcastic smile and crack about something-or-other that'll make her forget that he even looked in her direction.
It always works.
(Damn, he's good.)