Work meeting, then work, and work again tomorrow. GAH! Anyway, where are my thoughts on lovely, lovely Cheren.
My OTP for Cheren is Checkmateshipping, of course. They have been in love with each other for many years but, unlike Bel and Touya, they are less open about their feelings because they are silly little things. Cheren isn’t good talking about his feelings, Touko isn’t good at juggling her personal life and her position as the hero of Unova. I didn’t always ship this but instead came to love it more and more the more I played the game. Now I can’t imagine wanting Cheren to be with anyone else as much. There is something attractive about the “Ugly Ducklett” getting the girl. The Beauty and the Geek. Of course, Cheren is something of a "sexy senpai" now so now he’s more Swanna than Ducklett. Ultimately, they are the true “will they, won’t they” of the story in my headcanon and I feel it would be that way in the rest of the fandom were it not for N. Of course, there is Grandmastershipping. I wish people actually wrote it decently sometimes.
My most hated ship for Cheren is Dualrivalshipping. Again, I did actually used to like it… but the longer I played into the game, the less I saw it ever happening. The differences between Cheren and Bel’s personalities would clash rather than compliment each other. She’s too flighty for him, and he’s not the sort of person to find it “cute”… he just thinks she’s a little air headed He’s there for her when it happens, but in terms of a romantic relationship, it is abundantly clear that ultimately Cheren feels closer to the PC than the “dual” rival. The fact that at the start of BW2 Cheren hasn’t even seen Bel for two years suggests that the glue that held them together was Touko (or Touya, if you are a boy - in my headcanon it’s Touko, and Touya is still in Unova). Either way, they clearly aren’t as close as they used to be and are just friendly acquaintances now. I do think Cheren cares for Bel, though. He just doesn’t view her romantically.
My most unusual OTP for Cheren is not so unusual as it is complicated, and that is Hairoshipping. The reason it is confusing is because I see Cheren as part of this huge hierarchy of love interests. In my mind, the moment Mei saw Cheren at the new Pokemon gym she developed a mind-numbing crush on him. Unbeknownst to her, her brother Kyouhei’s friend Hugh has a crush on her. Cheren, meanwhile, certainly doesn’t get how much Mei fancies him and allows himself to be repeatedly tricked into going on dates with her - dates that Hugh goes out of his way to muss up. The truth is Hugh thinks the world of Cheren too. He is a trainer he aspires to be, because he is a young man who took on Team Plasma with the Hero and won. So he idolizes Cheren and so wants to outdo him (“I’ll become better than Cheren…”) in order to make himself worthy in Mei’s eyes. Mei, who is a natural-born trainer (Much like Touko), is someone who Cheren has a special fondness for because he sees the same spark in her that once lived in Touko - so he (unwittingly) indulges her and her crush. Told you it was complicated. Meanwhile, Kyouhei’s love life is blissfully simple as he rides the ferriswheel repeatedly with Ruri. ;)
My favourite friendship for Cheren is his student/mentor relationship with Alder. I think it really adds to the richness of the two characters, that Alder himself sought only strength and he lost his Pokemon to illness - you really get the sense that he never wants it to happen again to someone else. You really get the sense that Alder helped Cheren… and you can also believe that one day Cheren will become the Champion himself.
Make it happen, Game Freak.
My headcanon for Cheren is very crazy and numerous. So just sit back and let you reality fold away for a second while you read this:
Everyone has an OTP, right? Everyone has things they like, right?
Well imagine the future where your OTP is married and has kids, and their son or daughter (usually their daughter because, in the words of Dawn from Buffy the Vampire Slayer), girls are cooler.
Now imagine them being every bit as good as their parents and better. Imagine them with superpowers. Imagine them shaking up the system. Imagine them taking down demons in one swoop.
Imagine them being their verse’s answer to the Messiah.
That’s why every fandom wants their OTPs to have kids, so they can start off with the fresh meat of their offspring.
This is my headcanon for pretty much every show I’ve ever watched. I’ve always imagined a future.