There was a TV-Movie that aired maybe 15-20 years ago, either on Disney Channel, Nick, or maybe even as an ABC "Afterschool Special" (if they still had those in the late 90's/early 00's). The plot is: a young boy is being pursued by a bully. He finds himself backstage of the school auditorium where costumes and wigs are stored. He hastily dresses in drag to disguise himself and outwit the bully. However, the bully finds himself attracted to this "girl," who explains that "she" is the "sister" of the kid he's been tormenting, and admonishes him to leave him alone. The bully apologizes and asks the "sister" out for dinner. "She" rejects the notion, until he says that if "she" will go out with him, he'll never bother her "brother" again. After he leaves, "she" stumbles upon auditions for the school's production of "Cleopatra." "She" reads for the role just to avoid suspicion, but is immediately chosen for the lead role! So, between her male suitor and the play, "she" is forced to perpetuate the charade. All goes well until the night of the play, when he accidentally "outs" himself to the whole school when his wig falls off as he takes a bow during a curtain call.
The entire thing used to be on YouTube, but was probably kayoed by the copyright police. I do recall that many of the young actors had barely-disguised Canadian accents that slipped every so often ("I'm SO-rry ab-OOT bustin' into your changing room..."), so it might have even been originally produced by YTV or another Canadian kids' channel. I don't even know the title of the movie, so if it sounds familiar to anyone, any information would be welcome.
If it helps with recall, there's one silly exchange that sticks with me because it made me chuckle. It took place as the bully and the "girl" meet for dinner:
He: You look beautiful.
"She": Thanks.
He: And what's that amazing perfume you're wearing?
"She": Dandruff shampoo.
He: Oh.