Top 10 AdvanceShipping Moments

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10. Ash saves May from Harley's humiliation (A Cacturne for the Worst)
Boy, do I hate Harley. And watching Ash snap May out of the humiliation-induced shutdown he inflicted on her was satisfying for me.

9. Ash and May with the Luvdisc (The Temple of the Sea)
An encounter with a school of Pokemon the Pokedex associates with romance, couples, and love? Yeah, they weren't even being subtle with this one.

8. "Don't start something!" (Destiny Deoxys)
Destiny Deoxys doesn't impress me; this is literally the only scene I remember in full detail.

7. May roots for Ash over Norman (her father)
It says a lot about your relationship with your father when you root for your friend over him. I guess Ash just made May feel important to him. Too bad the anime never expands on this.

6. "Spoken Like a Man" and stepping in during the climax (Once in a Mawile)
Typical Ash...getting teased for being dense. Although to be honest, I like the later events of the episode more, where May takes initiative and she and Ash head off to the rescue.

5. Ash saves May in the canyon (All Torkoal, No Play)
I always loved this moment, but I think making a music video centered around it two years back made it stand out even more for me.

4. Ash comforts May after losing with Bulbasaur (Cruisin' for a Losin')
Ash is usually short-tempered and not one to apologize easily. But here, when May yells at him, he doesn't yell back, a noticeable contrast to his behavior in "The Bicker the Better." Later, when May is alone outside, he comes out and comforts her, even admitting that she was right about one thing earlier (even if it was for the wrong reasons). I guess he sees a bit of himself in her at the moment.

3. All their moments in Grass Hysteria
Most people only focus on them holding hands in this episode, but I love how they spend half the episode on their own together. They even work together to take down Team Rocket! Would that they could do that more often.

2. The Terracotta Ribbon
Pretty much THE definitive Advanceshipping hint. The battle that ended in a tie cemented May's character growth from a student of Ash to his equal. And considering an earlier character fantasized about splitting a ribbon with her boyfriend...hmmmmmmm??? Even those who don't see it as a romantic hint still acknowledge it as the ultimate symbol of their bond. Those who do, meanwhile, consider it the ultimate symbol of Advanceshipping.

1. The Date Expectations Climax
Yeah, there was no contest for me on this one. I'll be honest: as a kid watching this episode, when Ash and May got separated from the others, I internally cheered that they got some time on their own. The climactic scene where Ash and May have a heart-to-heart is the most intimate moment the two share, and it's my all-time favorite scene in the anime. Not only is it tender and sweet, but it teaches kids an important lesson about self-sacrifice. Better yet, it manages to do this without shoving it in your face or botching it in any way, a rarity for a series that has a knack for doing just that. In short, this scene is one of the most beautiful scenes in the entire series, capturing the heart and soul of Pokemon like few others can. For that reason, this is hands-down my favorite Ash & May moment, as well as my favorite Pokemon anime moment of all time.