Winter

As Contests are derived from the Pokémon League and were made in their modern form by one of the most well-known Pokémon Masters of her era, SHIROGANE Akari, Contest season and League season tend to occur over the same period of time. In Hoenn, Contest season starts in the winter, a mild annoyance to young trainers who want to be coordinators.

Drew Rosenblatt started in the winter for his third season, his second without the disadvantage of starting in the spring, feeling confident as a young coordinator would. Of course, the flood of new coordinators would come as the seasons change.

Spring

This is the season in which trainers tend to start their journeys due to the league season and school year being connected.

Maytal "May" Rubinstein had failed out of school. She had met with an experienced trainer, Satoshi "Ash" Ketchum, who didn't have his Pokémon with him and a girl, Serena Zarins he had met long ago who was unsure on her path as May herself was. Satoshi was deported, and Serena took up the guy's goal in his honor. Rounding out the group were IWAO Takeshi and May's younger brother, Masato "Max" Sugita.

Before then, however, she encountered contests. May is from Akagi City in the Johto region, probably the city in the region most noted for its contest culture, with the gym leader being a top coordinator, having won the 1996 Sinnoh Grand Festival. She wasn't unfamiliar, but she didn't realize how interesting anything Pokémon related could be.

She'd soon meet her most influential rival.

Summer

They meet while May practices her first appeals, May accidentally flinging a Frisbee™ frisbee at him. Drew initially dismisses May, thinking her to be some casual.

They then compete in May's first contest. She passes the appeal round first go, to Drew's surprise. They end up matched together, and she loses. Drew ends up losing to a guy named Robert.

May vows to never lose to him again. Yet she continues to lose to him.

May does end up entering the Grand Festival, becoming a notable coordinator without really trying. It does help that she posts a lot online, being probably one of the first major Pokébloggers.

Autumn

They meet at the Grand Festival. May then does something spectacular.

She wins against Drew.

She does lose against Robert in the finals, but one of her big stumbling blocks in coordinating is something she has found herself finally able to defeat.

The two meet at the beach, and they have a heart-to-heart. Drew is honest about something.

May reminds him of some of the most talented coordinators and lists some names.