Disclaimer: I own this fanfic, but not the characters themselves.
Author's Note: Yeah, yeah, a good eighty percent of Pokémon fans will probably hate me for not liking Hilda with N… But while I like N, I tend to avoid shipping him with anyone, so I really like CheckmateShipping. Oh, and in my personal head-canon, Hilda and Hilbert are siblings, but apparently several other people support that idea too so I doubt I have to worry about complaints on that, at least.
30 Sentences: CheckmateShipping
Glasses
Cheren may as well be blind without his glasses, though trying to make out Hilda staggering around with them on is almost worth it.
Wild
Hilda's endless energy is similar to yet different from Bianca's general breeziness, and while Cheren would never admit it, his drive for strength causes him to want to find a way to "tame" the brunette.
Girl Talk
Every time Hilda gets on the Ferris wheel with Aurora, the waitress gets giggly and asks her if she has a crush on anyone, and although she doesn't say it aloud, Hilda's mind instantly goes to Cheren.
Admiration
Despite the fact that Cheren started out with a Type advantage against Hilda, she always wins anyway, and she can't help but wonder if the look on his face is jealousy or admiration; she wants it to be admiration.
Teasing
It's rare to see Cheren blushing, but Hilbert asking him how he feels about his sister works every time.
Oblivious
Hilda sometimes wonders if her Serperior is hiding something from her, as the Grass-Type always looks smugger than usual when she sees her trainer with Cheren.
Similarities
Confidence is one trait Hilda and Cheren both share, although they express it in wildly different ways.
Secrets
Cheren thinks it's really easy to get annoyed with Bianca when the blonde smiles knowingly every time Hilda comes up in conversation but refuses to tell him what's so amusing.
Stupid
Every time Cheren visits Nimbasa City, he remembers how much he hates Ferris wheels, but perhaps it wouldn't be so bad if Hilda was there with him — he then hastily dismisses the idea as silly and childish.
Reminders
Marshall really is a lot like Cheren, and Hilda couldn't help getting distracted when she fought the Fighting-Type specialist, letting her mind drift over thoughts of her childhood friend.
Subtlety
While most people would find it easy to miss, Cheren notices it when Hilda's posture and tone of voice start shifting ever-so-slightly when she's around him.
Ridiculous
All the trainers Hilda usually meets up with at the Ferris wheel have caught the wishful little grin on her face as she stares idly out the cabin window, which causes her to kick herself mentally; it's like she's turning into one of those romance-story heroines she hates so much.
Routines
Hilda showing up at Victory Road every day makes for a good routine — that's all it is, a routine, Cheren insists.
Wait For It
Lately, every time Hilbert takes Bianca out anywhere, the blonde asks him if he thinks his sister will ever admit how she feels about Cheren; Hilbert just grins and tells her they'll realize it eventually.
Group Mode
Apparently, all of Hilda's Pokémon, not just her Serperior, are hiding something from her, as when they catch her staring at Cheren for a bit too long, Simipour and Galvantula share a look indicating that they're trying not to laugh.
Trickster
Cheren swears that Hilda's Scrafty intentionally pushed his trainer into him, but that doesn't stop his hands from lingering a bit too long on Hilda's wrists as he helps her up.
Denial
Hilbert finally asks his sister how she feels about Cheren, and while she adamantly claims she doesn't feel anything special for him, the small quiver in her voice gives her away.
Blind Date
Bianca refuses to tell Hilda who she'll be meeting at Nacrene Café as she forces the brunette into a dress she normally wouldn't be caught dead in, and Hilda can think of only one person who would make wearing a dress worthwhile…
Blind Date II
Cheren's Unfezant dutifully drops him off in front of the Nacrene Café, and when he sees Hilda standing there by herself in a very nice dress, he finds himself getting tongue-tied instead of being annoyed at Bianca and Hilbert for setting them up.
Awkward
Cheren wants to give himself a good punch in the face after his stomach does a weird twist when he sees Hilda standing a little too close to Chili one time.
Denial Reversal
When Bianca tells Hilda her suspicions about how Cheren feels about her, she bursts into laughter; she's known him for so long, so wouldn't she be able to tell if he liked her that way?
Trickster, Round 2
Hilda's Scrafty seems to be getting awkward timing down to a science, as one day he manages to push Hilda over in just the right way for her lips to line up with Cheren's mouth.
Trigger
They really had to give Scrafty some credit, as Cheren kissed Hilda quite intentionally less than ten seconds later.
Finally
They were both a bit embarrassed, as both Hilda and Cheren were hardly the romantic type, yet neither of them was really surprised to hear the other admit their feelings either.
Sinking In
Cheren had to wonder why it hadn't been blatantly obvious before; there were so many little details that made perfect sense now.
Adorable
Hilda has to admit to herself that the way Cheren reaches over to hold her hand, only to get flustered when she teasingly holds both of his, is strangely cute, mainly because it's so unlike him.
Like a Battle
Cheren eventually notes that Hilda kisses quite similarly to how she battles — she strikes quickly yet decisively.
Interruption
Cheren had always enjoyed reading, but he stopped minding Hilda grabbing a book out of his hands at the most inopportune times if she gave him a peck on the cheek afterwards.
Opinions
When Hilda asks Cheren if he'll ever get contact lenses to replace his glasses, he says that maybe he'd do so if she thought he'd look better, and she's flattered that her opinion is starting to matter that much to him.
Cliché
Bianca excitedly asks if she and Hilbert can go out on cute double-dates with Cheren and Hilda now, and while Cheren rolls his eyes at the idea, it does sound a lot more fun than he'd ever admit.