#hundredthshipping

For starters, I've decided that 100thShipping gets to exist in the same universe as ChampionSuccessionShipping because that's more entertaining to me. So all of my usual Hoenn boys headcanons apply. I had already decided pretty early on that Steven and Wallace had a pretty open relationship, so Brendan's allowed to have a little fun on the side.

I already talked a bit about May and Lisia in this post (but I've decided that May and Lisia first meet in Slateport instead of Fallarbor because I'm impatient.) After becoming neighbors, May and Brendan initially bond through Pokedex related research and fieldwork and end up traveling together often, which leads to them becoming fast friends. Brendan and Lisia mainly connect through their love of contests. When May and Lisia meet through Brendan, they hit it off instantly.

May is laid back, down to earth, and a little weird, so Brendan finds her very easy to talk to. May admires Brendan's seemingly natural battling skills and hopes that she can learn a thing or two from him and get stronger.

Brendan is drawn to Lisia's effortless confidence both on and off stage. Lisia loves finding a hidden gem and seeing how it shines under the right light, and she's certain that she's found something special when she scouts Brendan. She can see his potential and the passion he keeps hidden, and she's excited to squeeze it out of him (she and Wallace have this in common.) She means well, but she often comes on too strong and is a lot for Brendan to handle (another thing she has in common with Wallace.)

May and Lisia are both free spirits and weird girls who want to have fun. May can list off her favorite off-putting Pokemon facts, and Lisia can recount her wildest encounters in the contest hall dressing rooms, and it only makes them fall harder for each other. They also enjoy doing a little mischief together, which often includes testing Brendan's boundaries and seeing how flustered they can get him.

May and Lisia come from families where physical affection is incredibly normal. They're not shy about hugs, kisses, and cuddling. Brendan is actually pretty comfortable receiving physical affection from women (but he gets easily flustered by men because his mom gave him hugs and his dad didn't) so he's not too bothered with the clearly platonic displays of affection. However, the girls (Lisia especially) have a very different idea of what is considered normal platonic physical affection, and they also just think it's fun to test his limits. It takes some time, but Brendan does eventually warm up to the girls' preferred level of casual intimacy.

Personally, I'm a big fan of friends being intimate or having casual sex and it not being weird, so I've injected a lot of that energy into their dynamic. For the most part, Brendan's relationship with the girls is platonic, but sometimes the line between platonic and romantic/sexual blurs. At first, Brendan is very confused when the girls blur that line as he's unaware of the concept of polyamory. The girls have to reassure him that messing around won't ruin the girls' relationship.

Some other random headcanons: Lisia is the tallest. She's 5'7 (170.2 cm) (Brendan is 5'6 (167.6 cm) and May is 5'2 (157.5 cm)) Lisia is also the oldest at 19. (Brendan and May are both 17)

I feel like I'm all over the place, and this is getting long, so that's probably enough for now, but first, here's a bit more info about the sketches:

Image 1: Whenever they camp out or stay at a Pokemon Center, Brendan usually ends up in the middle of the cuddle pile. He doesn't mind, but it confuses him. He assumes that the girls would want to sleep next to each other since they're dating. May and Lisia do like cuddling each other, but they like stealing Brendan's body heat more.

Image 2: May and Lisia love cheering on Brendan when he battles.

Image 3: These three are always looking out for each other in different ways. Brendan tends to be more socially awkward and prefers to avoid confrontation over little things, but May refuses to let her bestie be a doormat and will happily rip into someone on his behalf. (However, the girls aren't as confident in more serious/dangerous situations, so that's usually when Brendan will step in.)

Image 4: Lisia has no fear and sometimes this is a problem. She is often a liability when she joins them during their fieldwork. After I drew this one, I decided that Lisia should convince Brendan to help her catch that Zangoose.

Image 5: At some point after I came up with Brendan's contest costumes, I thought it would be cute to give Lisia a Clefairy and design a costume to match. This is a first draft of that costume. Once Brendan hits master rank and becomes a popular contest star, he and Lisia get the chance to duet. (May is of course cheering both of them on)

Image 6: They're playing Zelda.