Boy Meets World/WMG

Topanga's sister was murdered.
Nebula died violently and the resulting trauma triggered poor Topanga's rapid personality shift, as she decided to abandon her granola girl tendencies in favor of her big sister's more traditional teenage-girl personality traits. Her hippie parents also rejected their counter-culture roots in an attempt to cope, a road which eventually led them to divorce. These events are too painful for Topanga and her family to speak of, so everyone has reached an unspoken agreement to pretend that poor Nebula never even existed.
 * ...holy shit, that would actually make for one hell of an awesome darkfic AU.

Cory has secretly been trying to get Topanga to gain weight.
Cory prefers a fuller figured girl but he's still deeply in love with Topanga. He can't bring himself to admit his preferences, in case she takes it the wrong way and gets offended, so he decides to simply start guiding her towards gaining weight. In "She's Having My Baby Back Ribs!" (and note the title), we see that he offers to make her "usual" breakfast, which is apparently a plate full of waffles soaking in syrup and topped with butter. That's apparently what he makes for her, for her to eat in bed, every morning. Coupled with the utter lack of hesitation in his voice when he tells her that he loves her no matter how big she might get, suggests that not only does he not mind her being overweight, he loves it!

Shawn Hunter came out of the closet about his crossdressing after the episode Chick Like Me S 4 E 15.
Think about it. He was clearly in the closet about his desire to crossdress up until that episode. He actually admits to Topanga and Cory that he has thought about "this" (crossdressing) before. He's thought about it often enough to have a preferred female identity, that of "Veronica". And he has already perfected the female walk, explaining that "Girls are my area. I like girls." So we know that he wants to crossdress, and that this article gives him the perfect opportunity to try it and then either pass it off as a favour to a friend that scored him a lot of brownie points with the girls of his High School...or to take this opportunity to come out to everybody in the school newspaper.

How do I know that he came out and continued crossdressing? Well, even though we never see him crossdress on screen again, there is another episode of Boy Meets World about crossdressing. What A Drag features Shawn's older (long-lost, half-)brother Jack and Cory's brother Eric, having antagonised a psychotic local thug, decide to evade him long enough to at least finish their exams by passing themselves off as women for the duration. Who do they immediately turn to for help and advice on how to be women? An actual woman, perhaps? Nope! They go straight to Shawn, who tutors them in how to "finding your own inner woman".

Later, when Jack goes back to dressing like a man, he over-exaggerates everything male about himself. Shawn actually points out how much less secure in his masculinity Jack must be if passing as a woman caused such a strong reaction. He even seems relatively unphased when Eric also decides to continue crossdressing.