I roleplay Flynn for an RP group on tumblr (flynn-eugene dot tumblr dot com) and every week our group has a different prompt to write a drabble about our character for a certain theme. These are my drabbles, mostly filled with my headcanons and backstory for Flynn.
The group is a Rise of the Brave Tangled Dragons group (a Rise of the Guardians/Brave/Tangled/How to Train Your Dragon crossover) but these drabbles are very Flynn-centric and you can easily read them if you've only watched Tangled.
The tower looked like something out of a fairytale. In fact, it looked like something out of The Adventures of Flynnigan Rider. It looked like the perfect place to hide.
The satchel bounced against Flynn's side as he raced through the clearing towards the tower. He could almost feel the power of the crown through the cloth. And by power, he meant money. Enemy kingdoms would buy this for three times the fortune he needed to get himself his mansion. No more alliances with ruffians like the Stabbington brothers. He could live the life of a rich man.
When he reached the tower, he walked around its base a few times before deciding there was, in fact, no door hidden beneath the thick carpet of ivy that crawled up the high stone walls. There was, however, an open window high, high up at the top of the tower. He grabbed a couple of the arrows the kingdom's guards had so graciously lent him and tested them, stabbing them into the crumbling cracks in the stone.
He'd climb up there Flynnigan Rider-style.
As it turned out, Flynnigan Rider-style was exhausting, and Flynn nearly collapsed when he finally crawled through the window. He didn't even bother to look around the room; if he had, he might have realized the place was more inhabited then he'd thought.
Instead, the back of Flynn's head was introduced to a frying pan.
When Flynn woke up, head throbbing, tied to a chair by a length of thick blonde… hair? Yes, thick blonde hair, the last thing he'd been thinking of was friendship.
Friendship was also the last thing he was thinking of when he tried to sweet-talk his way out of the psychotic blonde girl's tower. It was even the last thing on his mind when he agreed to be her guide to the dumb lights, of all things.
In fact, Flynn wasn't really sure when friendship had become the first thing on his mind when he thought of Rapunzel.
All he knew was that now it was.