Sommelier (Dento/Cabernet): I've been extraordinarily interested in this ship from Cabernet's first appearance. Every time she shows up, it’s like she tries even harder to hate Dento, despite the fact that he’s totally sweet and supportive of her, and genuinely tries to help her be a better sommelier. She blushes and denies that she’s learning from him, and she has the most crazed obsession with the guy. I think her "eternal hatred" of him is her way of trying to mask the fact that she really likes him.
HeatTag (Conway/Dawn): Some people think it’s creepy that Conway stalks Dawn. It kind of is. That’s one of the reasons I like it. xD Conway, the calm, brilliant trainer falls for the sweet, emotion-driven coordinator… aww.
Contest (Drew/May): One of the few ships I love that’s actually reeeally popular. Drew started out being overly critical and fairly rude. But he warmed up to May and she to him, and it didn’t take long before he really respected her as a coordinator. The roses he gave her are traditionally a symbol of love, or at least admiration, and they had several very sweet scenes (including a great deal of blushing) and the sunset scene before she decides to follow him and their other coordinator friends to Johto was perfect.
Split (Clay/Elesa): I’m probably one of the few people in the world that ships these two, but I can’t help it; I ship it pretty hard. I think there’s something endearing about the young model (I always picture Elesa in her mid-twenties and Clay in his mid-forties) softening the gruff miner king. In both the games and in the Black and White chapters of Pokémon Special, Clay and Elesa pair up to fight the Sages and Shadow Triad, respectively. When you first meet him, he remarks that you’re the Trainer Elesa was talking about. And the thing Clay says to the player when he starts the gym battle? “Well... Think it's about time to see fer myself what it is about yer skills that makes a Gym Leader like Elesa take such a shine to ya.” He starts the battle referring not to himself, how he got to where he is, what kind of Pokémon he trained, or anything at all about Team Plasma; he wanted to know why Elesa liked you, and didn’t even bother masking the fact that he believed Elesa was a fantastic Leader. That’s interesting to me, given the type of person Clay is (fairly self-centered, confident, rude, and impatient – but that’s why I love the guy).