I'm curious about TipShipping and LemonMeringuePieShipping! Do you have any headcanons for them? Or even the kids?
I’ll do the HC for the parents, mostly because I haven’t planned out the kids yet. Also, I’m basing my knowledge of these characters from the games and information on their bulbapedia page. Mostly because I have never watched anything after DP ended. So I’m sorry if there’s mistakes in the character...? IDK
Cilan and Trip coincidentally met up during their solo travels in Johto and decided to just talk about what has happened since the end of BW or something
I mean yeah they’re like adults now but there’s still going to be small little friendly banters here and there
They kept in contact with each other after parting ways to continue on with their solo journey and stuff
They’ve become pretty good friends over the years too. It got to the point where both developed romantic feelings for each other
One day, they ended up in the same place again out of mere coincidence. Cilan was pretty self-conscious about his feelings for the other guy, but it was Trip who made the first move. Which kinda worked seeing how he’s pretty blunt and straight-to-the-point.
So they p much started their relationship slowly, decided to travel together because they’re pretty much in the same region together and will bound to meet up again somewhere - so why not travel together? Keep each other company? All the works.
Cilan’s still dreaming to become the best Connoisseur ever, but Trip decided to become a professional photographer instead of becoming the best trainer ever.
Years past and they’re married and have 4 kids: Parsley, Sage, Rose-Mary, and Thyme (they all have middle names, but I don’t have my phone with me so I can’t really remember their middle names)
Except, as time past, they were both too busy with their own dreams and ambitions that they sort of lost that spark they had when they were younger. Possibly from how busy and hectic their lives are now that they have 4 children to care for.
Both mutually agreed that it wasn’t working out anymore and decided to divorce.
Trip took custody of Sage and Thyme; while Cilan took Parsley and Rose-Mary.
They’re both happy with how things turned out - and they’re still pretty good friends despite what happened. They’ll let the kids visit each other, maybe spend the holidays there or something so it doesn’t seem like they’re keeping their kids away from each other and their siblings.
Clemont decides to visit Cilan in Unova b/c they still keep in contact after meeting each other years ago in Kalos and stuff.
Also prior to Cilan and Trip getting together, Clemont had like, an unrequited crush towards Cilan - but decided not to do anything or say anything b/c he was worried. And then he later felt like shit after finding out that Cilan and Trip got together, got married, and had kids.
So Clemont visits Cilan and was really surprised to find out that Cilan and Trip were divorced. He lowkey was relieved and excited because that meant he had a chance - but he didn’t want to do anything b/c he’d probs be taking advantage of the situation and that’s a no-no
Clemont meets Parsley and Rose-Mary and was not even surprised that they were named after herbs (he also found it interesting that the names of his four kids were inspired by the song Scarborough Fair - apparently that song is Cilan’s favourite)
Clemont ends up spending a lot of time with Cilan and his kids, even helping Cilan out with house stuff because Cilan was busy with his own thing.
Cilan felt bad for having Clemont do so much b/c Clemont is technically a guest at their house, but Clemont is fine with it (I mean, if it means being able to spend time with his crush, so be it.)
A couple months has past and Clemont decided to confess to Cilan. Cilan was p much taken aback. He was flattered, but he had to think about it because I mean, he did divorce Trip - who he has been with for a couple of years - and is still kinda not over it? Clemont understands and doesn’t push it.
Another month passes and Cilan p much reflects on everything that has happened in his life in regards to romance. His first relationship with Trip, their marriage, their kids, their mutual divorce. And now with Clemont, a friend from Kalos who literally spent every day at his place helping out with mundane house work. His confession, acceptance and understanding of Cilan’s current position and situation. The more Cilan thought about it, the more he appreciated Clemont. It got to the point where Cilan felt what he did before with Trip - but this time, it was with Clemont.
One day, Cilan pulled Clemont aside and poured out his feelings right then and there. It was basically a long-ass confession that probably took forty-five minutes. Clemont was surprised and really fucking happy because wow, it’s no longer unrequited feelings!
A few years later they got married and they have a child named Bailey Tifa [Cilan’s last name here]-Lemon