This is every single May/canon May shipping I can think of (except for Ash with May cause I ain't writing that one) Enjoy.
May and Drew
He was holding a bouquet of roses. A beautiful bouquet. A bouquet that looked like it came from a painting or one of those way-too-perfect photos. May could only stare at it in awe.
"A-are these-?" she asked, tentatively taking the flowers from the boy. "All for Beautifly?"
A small chuckle emerged from Drew's lips.
"No," he said, wrapping an arm around her waist a pulling her close. "These are all for her exceptional trainer… that I love."
May and Brendan
"Aw!" May snuggled the Poke-Skitty doll tighter to her chest. "Brendan this is perfect! I was looking for a new plush for my Secret Base!"
"Yeah well," the boy said, nervously scratching the back of his head. "I figured you would like cute things like this." May nodded.
"Yep, I love them!" She said. She then winked at Brendan.
"I love you too."
May and Wally
"U-um…Wally?" May asked nervously. The green haired boy was still hugging her from behind and May could feel her cheeks ready to burn off. "W-what are you doing?"
There was a slight pause before the boy answered.
"Stopping you from leaving." He said. He then stood up on the tips of his toes and kissed her cheek.
"I love you." He whispered in her ear.
May and Steven
"Is this…. what I think it is?" May asked, her heart beating fast. Steven nodded. He was holding out to her a ring engraved with a sapphire heart.
"Oh Steven…" She whispered. "It's beautiful."
Steven chuckled. "Well I thought that my girlfriend deserves only the best."
May smiled and slipped the ring on to her finger. It was a perfect fit.
"Thanks Steven I-wait…." May suddenly said, her eyes growing wide. She stared at Steven, shocked.
"You want me to be your girlfriend!?" She exclaimed.
Sapphire and Ruby
"What…in the world…is this?!" Sapphire screamed. Ruby just gave her a calm expression before answering.
"It's your Valentine's Day present."
"It's a freakin dress!" Sapphire yelled. "You want me to wear this?!"
Again, Ruby answered calmly. "Yes."
"No. No way, no how. No no no!" Sapphire said, shaking her head. "It's all frilly and pink and…and…it looks like what Lisia's wears!"
"Exactly."
Sapphire blinked. "Wh-what?" She asked.
Ruby looked her in the eyes, before looking away. "Lisia looks cute in her costume but…. I thought that you would look cuter if you wore it."
A silence came over the two. It lasted for five full minutes (a record for the two, actually) before Sapphire finally mumbled,
"Okay…I'll wear it."
XXX
My personal favorite of these are May and Drew, May and Steven, and Sapphire and Ruby. Yes, I am a MAJOR Hoennchampion shipping fan! More so now that I'm playing Alpha Sapphire. I'm just all like fangirl squeal when I see that guy! I mean, some might call it pedo- but I think that age gap is what makes it so attractive!
Happy Valentine's Day everyone!