Disclaimer: If I owned Pokémon, Hilda (and Hilbert, too) would've been part of the Pokémon World Tournament in BW2, just to make more shipping fuel for UroborusShipping a little closer to "it could happen" territory.

X-X-X

U is for UroborusShipping (Red & Hilda)

It was a snowy Christmas night. Red walked down the country road dressed up in typical casual clothing, plus a scarf with a Delibird on it that he got as a gift from Blue's sister Daisy. He was never really affected by cold weather, so the scarf did nothing but add uncomfortable heat, but it was a gift and he promised to wear it at least once. He was so far from Pallet Town, he couldn't see it in the distance. He'd promise to meet Hilda halfway since she was staying in Viridian City in the Pokémon Center, just to escape the teasing looks, cries of 'awww!' and other embarrassing aspects of giving a gift to your first love in front of others.

Red stopped by a frozen pond and began to check his hair. He never really cared for primping before except to please his mother, but now he had to look good so Hilda wouldn't tease him for it. He felt the pocket of his jacket for the small ring box and nodded. He didn't feel very confident and it uncharacteristically showed on his face. He took a deep breath, expelling a cloud of icy mist in the process, and looked at Pikachu, who was sitting on his shoulder. "Well, Pikachu. Wish me luck."

"Pi-ka," Pikachu mumbled before jumping off his trainer's shoulder to play in the snow.

"Hey, Red!" Hilda came running from the direction of Viridian City, dressed up in a white down jacket and boots. She came to a halt in front of him and smiled brightly. "Merry Christmas! How's your day been?"

"Fine. Yours?"

"Well, this is the first Christmas I've spent away from home, so I've been a bit lonesome," the brunette mumbled as she looked down at the frozen pond. "Talking to a screen's not the same as being with my family."

Red shoved his hands into his pants pockets. "You could've come to spend it with Mom and me."

"No, no. I wouldn't want to be a pest."

"You wouldn't." In fact, his mother practically pestered him for the last few days about inviting his girlfriend to spend the holiday with them. "You can spend the rest of the night with us. Daisy and Professor Oak will be there."

Hilda arched an eyebrow. "No Blue?"

"Blue's spending it with Leaf. He's certain his gift to her is gonna make her fawn all over him."

"Gift? Oh, right! Before I forget…" Hilda pulled out a small box. "For you!" She handed it to the dark-haired boy.

Red took the box carefully in both hands. It hadn't been wrapped and the only sort of decoration on it was a stick-on bow. He opened the box to reveal a watch with a red leather band and what he hoped were fake jewels encrusted around the watch's face.

"I wasn't really sure what to get you as a gift. You're a real tough person to shop for! I felt so embarrassed asking your mother if there was anything you wanted or didn't have…" The brunette girl began to mutter things under her breath about useless store clerks while her boyfriend continued to look over the watch. "Those gems are fake, of course. I never got why a person would wanna wear a watch like it was jewelry…and you seem like the frugal type."

The red-clad teen flinched. Frugal? That was just a nicer word for cheap. Was it because of his White Day gift? He thought baking those cookies would be enough to repay her for all the trouble she went through, trying to make chocolate he could eat without being afflicted by his allergy, but all that did was get her stuck in the hospital as they pumped her stomach. Maybe she thought the cookies were a sign that he was a cheapskate who wouldn't 'triple the return' and get her fancy gifts? Suddenly he felt like her Christmas gift was a bad idea.

While Red struggled internally, Hilda stood before him with a confused expression. "Uh… Red? Are you okay? I don't like it when you fall silent like this. All the other times, it's okay, but…" She jumped a little when closed the box and slipped it into his jacket.

"Thank you. It's really nice." Red smiled and it made Hilda feel ten times warmer than her jacket did. His smile was immediately replaced by his usual apathetic expression and he pulled something else out of the jacket. "This is for you. I…I hope you like it." It was a small jewelry box, like the kind used for rings and earrings. The thought of Red buying jewelry for her made the brunette girl blush. He didn't hand over the box, though. Instead, he opened it, revealing a silver ring with a little diamond in the middle. "It's not very ostentatious, but…"

"Huh?! I-I-I don't mind! I'm just glad you were kind enough to buy this for me!" She bent over to better observe the ring's diamond. "Look at it sparkle! It actually looks real!"

"It is real."

Hilda jumped back in surprise. "Say what?! That's a real diamond?!"

"I know it's small—"

"It's not that it's small! It's that it's real! Geez!"

Red stared at her, confusion apparent on his face. "So…you don't like it?"

"I still like it." It just made her gift feel cheap in comparison. "But really, with the diamond ring and you holding it like that, it almost feels like you're asking me to marry you…!"

"Eventually."

Hilda's eyes widened and she blushed once again. "E-eventually?"

Red nodded. "Eventually. I'd like us to get married eventually. When we're both older and more prepared, of course."

A little part of Hilda wanted to ask if this was a joke, but she knew Red well enough to know that while his sense of humor sucked when he wasn't saying anything sarcastic, he wouldn't joke about something as serious as engagements and marriages and proposals… "Why? Just…tell me why the proposal."

"Because I love you. I'm not the best at expressing my feelings, and I know it sounds stupid…but is it really that bad that I want to spend the rest of my life with you?" Yes! Yes it was! Because she's a 16-year old girl and he'd be 20 in a matter of months, and no matter how much he wants them to last, he can't guarantee they will!

Silence seemed fell upon Route 1. Pikachu forgot about his little snowman and was now looking up at the two humans with a slightly peeved expression. Leave it up to Red to not be subtle with something like an engagement.

Hilda took a breath. "I…I'm not sure. I-I mean… How do you know we won't become one of those couples who married their high school sweetheart only to wind up hating each other in the long run? How do you know if we'll even last long enough to get married?" She didn't know why she said that. She blamed common sense, because every irrational part of her liked the thought of them being engaged for years before they tied the knot.

"…We'll know for sure when we're older, won't we?"

"…Okay. Let's get married a couple of years down the road if we can still stand each other!" She exclaimed suddenly as she started to laugh despite the anxiety and the worry that they may not actually last. This was just begging to be another teen love sob story, but when Red managed to get a hold of her hand to slip on that ring, she decided that she didn't care. Instead, she said, "Y'know, you did that all wrong…"

Red arched an eyebrow. "What?"

"You're supposed to bend on one knee and ask me if I wanna marry you. But I forgive you for that."

"Hm…" Red fell silent for a moment before he wrapped his arms around her and buried his face in her hair. "I really do want to be with you forever, y'know…"

Hilda smiled and enjoyed the closure with her new fiancée. "Yeah. I do, too. …By the way, does anyone else know that your gift to me was a layaway on a marriage proposal?"

Red shook his head. "Nope."

"Huh…" Hilda strained to look down at the ring on her finger in her position and stifled a laugh. "Well, uh…this is gonna be fun to explain to our parents…!"