Fun thread. Here are some goofy ones I've encountered:
One pooner told me she had started on T because she believed it would make her ghost dad proud. As in, her dad who had died when she was a child subsequently became her imaginary friend, decided to helpfully inform her that she was trans; and that nothing would make him a happier ghost dad than seeing her be like her old man.
A female co-worker with two teenage kids told me about how they had trooned out because they were ugly and unpopular; and believed swapping genders would allow them to each be the new kid at their high school while still attending the same school (they were subsequently homeschooled by their mortified mother after this foolproof scheme to reset their reputations somehow backfired). I think the kids still live at home with their parents, despite being in their thirties, now. I remember that the girl used testosterone to grow a Vote for Pedro mustache, and was giving herself Herman Munster haircuts. The boy looked like that one scene from Spawn where the clown dressed like a cheerleader and danced around with poms.
A guy in a dress once bragged to me that the ritualistic abuse of amphetamine salts he required to "binge on David Lynch and Marxist literature" culminated in psychosis and a hospitalization which had "left" him trans.
The weirdest one so far is the girl I used to buy coffee from, who had pooned out in the belief it would make her a better cosplayer (that's not the weird part): She recently walked it back to announce that she had just been confused; and is actually "trans monster", identifies as a "gay, male monster", and puts on halloween store-tier vampire or zombie makeup, prosthetic fangs, and gothic clothing to wear while running errands around town. The years on T gave her a Rich Evans hairline; so she kind of looks how Peter Gabriel did in the 70's. She ended up marrying another pooner who does her own face tattoos freehand, and their wedding photos depicted the two of them feeding each other a Costco rotisserie chicken in a cemetery.