Jack Point for the headcanon meme? 😁
(this one took time because I have so much thoughts about this guy)
Jack and Elsie met as children back when he was part of the archbishop's household. (Bridget Maynard was a housekeeper there until her health started taking a turn for the worse.).They've been inseparable since, and when he got kicked out, Elsie decided to follow him.The latter actually makes Jack feel a bit guilty whenever things get rough. Jack is also the one that taught her to read.
Headcanon B: might not be realistic but hilarious
To everyone's surprise, he and Real Leonard Meryll get on like a house on fire. Leonard has a mischievous streak and actually enjoys Jack's sense of humour and Jack quickly catches on Leonard often uses his reputation as a bit of a stick in the mud to troll people. They're also both nerds.
He teams up with Phoebe and Leonard to help Phoebe get out of her engagement with Wilfred. Zany schemes ensue.
Headcanon C: heart- crushing and awful,but fun to inflict on friends
Jack always tells the archbishop of Canterbury story like a funny anecdote, but there's more to it: Jack was raised by relatives that only took him in out of obligation and who didn't bother hiding that they never wanted him. Soon he became too much of a handful for them and they "accidentally" "lost" him at a nearby town, leaving him to fend for himself.*Eventually he was taken in as an apprentice/ happily adopted by the archbishop's previous jester. When the man suddenly died right before a party a teenage Jack was pushed into filling in for him,still grieving and with no chance to mourn properly or even prepare an act. Oh he was funny, alright. Deep down he thinks that evening might've been the funniest he's ever been. Unfortunately the archbishop wasn't too keen on ruthless social satire, which resulted in a whipping and a dismissal.He's been more careful since, but that often makes him less funny than he would've been otherwise.
(*When they were kids, Elsie once asked him if he has family. He replied "None that want me" and that was all anyone ever got out of him on this subject)
Headcanon D: unrealistic, but I will disregard canon reality and substitute my own
In one alternate universe, Jack Point decides to leave England after the events of Yeomen.He gets on random ship; said ship crashes near the coast of Illyria, where he finds a job as court jester to a local count and his children.
He comes up with a new stage persona for them, sharper and bolder than his previous ones, and starts going by "Feste". He grows to genuinely care for Olivia and the people in her household, and they, in turn, grow very fond of him (well.except for Malvolio) .He's happy there, in a way.