Jack has rules about mentorship. First of all, his mentees have to have four things: drive, intelligence, humility, and chaos. It's a harder combination to find that one might think.
His next rule is that they have to be male. It's not discrimination, really; it's just that his mentorship is very immersive, and that kind of thing can be taken the wrong way. With an immediate subordinate, that's an issue.
He's already bent that rule once, with Thomas. When Jack met her, everything about her style made it pretty obvious she was a stereotypical lesbian: short hair, glasses, out of shape, and poor fashion sense. With no sexual tension between them, it was simple for Jack to fix all of those things, and the newly confident engineer that emerged was a huge asset to GE, in every dimension.
Although she isn't as much of a wreck as the pre-Jack version of Gretchen, Liz Lemon is equally in need of his help. Her sexual orientation isn't quite as immediately obvious, but the shoes clinched it for him: Lemon was OK to approach without fear of being misinterpreted. In the space of a week, he started to give her lots of unsolicited advice, to see how she reacted and see if his first impression was correct.
And indeed, Lemon is excellent mentee material.
So that she knew that he knew that she was gay, he fixed her up with Thomas. It was more of a ploy than anything else, but he was pleasantly surprised that the two of them hit it off.
There was just one problem. Lemon isn't gay.
Oops.
Now he's stuck. He's already sold himself on Lemon as his next big project. There's so much to be done, and all of her ills are so correctable. She could be a huge asset to NBC. And he finds he can't conceive of passing this challenge up. Aside from his criteria, there's something about her that intrigues him.
He's going to have to tread carefully here. It's easy for women to fall in love with him. The thought of them together is ridiculous – she's not at all what he looks for romantically - but his attention might give her the wrong impression. And who could blame Lemon for developing a thing for him? He'll have to find an opportunity to make it clear that that is not where this is going.
And to be honest, he has to watch himself too. He's never peered so deeply into the life of a heterosexual woman before. He probably knows Bianca better than he knows any other woman, and she never completely let her guard down in the way that his mentees do. And aside from the fact that she could use a little attention to her appearance, Lemon is not an unattractive woman.
So he's bending his rule again. Bending it so much that it breaks. But he has a feeling that Lemon is worth it.
END.