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Ages: 10-13

Started his journey in Kanto, getting Pikachu as his starter.
You should know the rest.

Ages: 14-16

After an encounter with Dawn in Alola, the girl went missing and he, along with some other friends went looking for her. But being the lucky (or unlucky) one, Ash was the one to find her. All the way back in time, in a Sinnoh of old. Hisui.

He and Dawn would spend an entire year in there —both in their and their friends and family's present perspective— before finally finding a way back to the present and their homes.

Ages: 17-19

Still taken back from the happenings in Hisui, Ash spent some time resting in his hometown at Pallet, which his mom very much appreciated.

He would deem the break long enough after a year, getting back on the road and more importantly back to Alola. Where he figured that the calmer atmosphere would allow him to get back into battling without the pressure other regions with their leagues put on him. It would also be a chance for him and his Pokemon to put their newfound connection to a test. So he took the Island Challenge again.

Soon after that, Ash regained his sense of adventure once again. And off to start another journey he went.

Such journey ended up leading him back to Johto, where he would meet and travel once again with Brock and Mity... and also Dawn?

After a chance meeting with in Vermillion, he and the other two would follow her back to Sinnoh to support her on the Grand Master Festival and watch as Dawn earned herself the win and became the first ever Master Coordinator in history.

Ages: 20-21

During a small trip to Sinnoh to try and get over his own bias against the region, Ash met with Dawn again. And after some very complicated ups and downs, they decided to start a relationship together.

Ages: 10-13

Started her journey in Sinnoh, getting Piplup as her starter. Meet Ash and you can watch the anime to see how that went.

Ages: 14-16

After some too many tries and failures in her coordinator career, Dawn tried to take a break going to Alola. She met Ash there and that sorta made her a little more confident to try again. Her plans were changed when she ended up sent back in time somehow.

When Ash managed to find the same fate as her and end up in Hisui, he would meet with an amnesiac Dawn. It would take a while, but she would eventually recover her memory and they both would eventually find their way back into the present.

Ages: 17-19

The adventure to Hisui didn't exactly leave them harmless and as such, both Ash and Dawn spent some time in their hometowns processing what they had experienced, as well as recovering.

Dawn would take the longest to find her courage to leave home again. With the fear of failing another contest circuit on top of the fear of the region itself, she was avoidant of starting another journey. But on her 18s, she would try again. Traveling Sinnoh one more time and participating on the newly format of Master Contests. She would eventually find herself the winner of the Grand Festival that followed this new format.

Ages: 20-21

After traveling with Ash to Pallet and having the boy ask her out on a date, they would try the real thing when they met again in Sinnoh. Things didn't go perfectly, but in the end they both agreed to stay in a relationsip.