Not really a headcannon but someone request this so I did a timeline of Georgie's failed breaks and vacations honestly don't know where I got the idea to not give Georgie a break, but it just started happening when I was writing.
Lost: Georgie is trying to enjoy a winter day with Pumpkin and Tessa, but Tessa loses Pumpkin and they end up searching for her the rest of the day
Adventures Of Pupsitting: Tessa begs Georgie to help her with makeup for an overnight trip, and she leaves Pumpkin with Lola. She ends up having to go home to find Pumpkin.
A Snowy Valentine's Adventure: Georgie is supposed to go see Tessa but there she refuses to leave Pumpkin with Lola so she goes to the airport to upgrade her tickets, but gets stuck in the snow so Lola has to watch Pumpkin
Dog Fight: Georgie is going to hang out with her friend Lily and relunctantly leaves Pumpkin with Lola, but Lola ends up not watching her, and Pumpkin gets in a dog fight which involves going to the vet
Where Am I: Georgie goes to help one of her friends, and then to hang out with her friend. But as always Lola messes up and Pumpkin gets stolen causing her to go home a few hours early.
The Adventures in Meeting Mal: Georgie is trying to do a normal day of work when the Queen sisters basically tell her that she's going to watch Mal so not only did she have her normal work to do she had to keep Mal entertained. Let's just say it didn't end well
A Normal Day NOT: Georgie goes to the park to relax alone while the Queen sisters watch Pumpkin. To her shock her normal day would be turned upside when Arrow comes and tells her that the queen sister have turned into dogs.
A Sleepover Adventure: Georgie relunctantly let's the kids stay at her house for a sleepover on her day off.
Build a Bear Adventures: That sleepover turned into Georgie having the kids an entire weekend, plus meeting Mal and Lola while they are out. And Mal wanting to spend the last night with them.
No Normal Pup: Georgie is just trying to hang out with Mira when they happen to run into an attempted suicide and try to help
Adventures Of Living With A Four Year Old: Although it seems like a normal day for Georgie and she would finally get a break Tessa calls up saying she needed her help. Little did she know this would flip her world upside down, and is left scrambling to reschedule lots of things while keeping important ones down
It Comes With The Territory: Georgie is just relaxing after finally getting up to her new normal. When she gets a phone call saying they needed her at the VA hospital pronto. It didn't end well.
Ava's Pupsitting Fail: Georgie is just going to hang out with Tessa, but of course she wasn't able to hang out to long because Mira and Mal call her telling her that Pumpkin drank some alcohol, and she has to rush back.
An Unplanned Vacation: Georgie is actually supposed to be getting a vacation and is going to Florida to visit her friend who was working there, but it doesn't go as planned or feel like a vacation when five kids and nine animals have to come along
Lily+ Lola = A Bad combination: Georgie is enjoying her day with Lily when she bumps into Lola and Mal again, and ends up having to take care of Mal.
I think I missed some, but these were the major one also thanks whoever requested this because you made me read some of my one shots I haven't read in literally forever and it was very enjoyable lol. Also don't worry Georgie will get a break I'm actually working on a mini story where she actually gets to go on vacation alone. Although I still don't know how crazy it will get 💖
