Credit: ABC Family Photo: Jack's Texting At Grant High in Episode 4.07, "Cute"

We all know how hardcore Jack is crushing on Grace, but no matter how many times he knocks on her bedroom door for a goodnight kiss, she’s just not feeling it. It might have something do with the fact that he had an STI (no, Secret Life writers, we have not forgotten about that whole thing), but one can never tell what Cookie’s thinking.

In Season 4, Episode 12, “Pomp,” Jack uses a school project to get closer to Grace, but will his plan work? If this project is for Sex Ed class, we’d say he has a pretty fair chance of getting in Grace’s pants.