AN: Alright, this chapter is actually three Omakes showing the potential romances and how I see them. As I said before, I'm worried about continuing a Ruby pairing because it could either change Ruby too much or too drastically change the version of Harry I'm crafting. That said, these three Omakes are the ways I would have the relationships for Harry with Ruby, Death, or Winter. The two who I don't pick for the pairing will still be a big part of the story but as sister like figures. Tell me in the review who you would like and why. Final choice is mine, but I want to hear what you guys think.

A Grimm Huntsman

Chapter 18

-Omake: Ruby-

"Come on Harry!" Ruby pleaded as she tugged at his arm, dragging him along with her to the kitchen as he gave a dry chuckle at the eager attitude of his small girlfriend. She wasn't into clubbing, or fancy dinners, or almost anything else involving going out. No, she insisted their dates being things like making cookies, or working on their weapons, maybe a movie night or a game session. The only time she was really willing to go out for a date was if it involved something like a fair. She was introverted, she was awkward, but she was his.

Raising his arm, he chuckled as she thrashed and wiggled, clutching it and trying to continue forward even as he held her up in the air "Harry!" Ruby whined, giving up her thrashing to pout at him "You promised!"

"Fine." He gave a sigh but couldn't hide his faint smile of amusement as he set her down and Ruby once more began dragging him off down the hall to the student Kitchen. She had made him promise to help her make cookies once a week, so she would always have a supply and sometimes she was even willing to actually share some of them. Finally reaching the kitchen Ruby began zipping about, grabbing bowls and ingredients as she squees happily, much as she does every Saturday when they do this. The inevitable Sunday cleaning when Goodwitch finds the mess they make is received with much less enthusiasm. Putting on an apron he began flipping through a cookbook he borrowed from Jaune, wanting to make something different than chocolate chip for once, not oatmeal raisin, not after last time he gave those to Ruby.

"Hnnnnn!" hearing the sound and feeling the tug on his apron he turns towards Ruby who's cherry red but pointing at her new apron with an expectant pout, the fabric reading 'Kiss the cook'. Smiling in amusement he leaned forward and kissed the tip of her nose as she squeaked before he began preparing the ingredients for macaroons.

"Those aren't chocolate chips." Ruby says confused at the stack of ingredients.

"We aren't making chocolate chip cookies, we're making macaroons today." Harry explains, never missing a beat even as Ruby makes an outraged squeak of protest.

"But chocolate chips are love and life! We have to make them!" she whined, trying to get at the ingredients only to give up when he holds the bowl up out of her reach. Seeing her turn and pout, arms crossed in a huff Harry smirked. Dipping his hands into a beg he flings a handful of flour at her, covering her head in the white powder.

"Ah!" he gave a fake monotone cry of shock "You've turned into Winter."

Her eyes narrow before she vanishes in a cloud of rose petals. Before he can find her again he feels something cold and slimy slide through his hair as Ruby cracks two eggs over his head, standing on the counter to get high enough to do so. "You know Ruby," he declared with faux seriousness as he wiped goop away from his eyes "this means war." The ensuing food fight ensured both that no cookies were made that week and that the next day's clean-up was the worst one yet. All in all, he rather enjoyed that date.

-Omake: Winter-

Jasmine perfume, the soft crackling of a fire, and the feel of soft hair beneath his fingers. They were in Winter's home in Vale, relaxing by the fire with some books as his lap became her pillow. They tried to mix up their dates between staying in and going out as well as who picks what. Today he hadn't felt like going out anywhere, so they lit a fire, made some dip, and were just enjoying each other's company.

"How's your book?" he asked, flipping through a classic from Remnant that Winter had recommended while she read one from his world, Pride and Prejudice in this case.

"It's wonderful," Winter smiles up at him, giving the hand running through her hair a squeeze "your world really did have some great writers."

"Same about Remnant." He smiled, raising the book up "The poetry about the shattered moon is especially nice."

"Beneath the light of shattered moon

The light spun in heavens loom

Drifting through the silent night

A guardian here till we regain the light

Monsters seek to spread eternal fear

All for naught as the moon keeps hope near"

Winter recites one of the first Remnant poems she introduced him to making him smile at the memories of their time together. What had started out as therapy had instead blossomed into something more. She knew when to push him to say more, when to let him keep his silence, when he needed space, and when he needed someone there with him.

"So, has Ironwood tried bringing you into his little war with Ozpin yet?" he asked her amused, unable to stop a chuckle at the thought of the competition the two headmasters had gotten into. Ironwood had been trying to poach him for Atlas academy since their first meeting resulting in both the General and Ozpin to get into a friendly…ish competition over getting him in their academy or keeping him. It was rather entertaining if he was at all honest.

"I made it clear to him that I was staying neutral in this." Winter smirked, her own eyes dancing with amusement "But I may have hinted that you hadn't been skiing before and were curious. And the Atlas academy just so happens to have a ski lodge up in the mountains for our students to relax. Too bad it's Atlas students only, if only a certain headmaster could authorize an exception to that rule. I'm sure there's a member of Atlas personnel who would be willing to escort you."

"You know, you would totally be a Slytherin if you grew up in my world." He can't help the grin at his girlfriend's deviousness as she smirked up at him.

"You know you love it." She grins with playful smugness.

"I know I do." Any response she had was lost as he leaned down and kissed her, their books forgotten.

-Omake: Death-

Death bounced up and down beside him as they waited in line for entry. Since she gained sentience Death had been taking her duties seriously, helping ensure the smooth journey of souls to the afterlife and in doing so viewing their memories. In doing so she had developed a bit of an addiction to 'life' and a hatred for the Grimm. People with interesting happy and long lives had the best and most memories to her so Death liked it when people lived full and fulfilling lives. Due to Grimm cutting lives short so often Death had a rather intense hatred for the creatures of chaos.

Right now, they were in line to enter a local fair full of rides, games, food, and even having a concert later that night. Most of their dates involved them going somewhere new as Death was addicted to experiences and to life. Handing over their tickets they entered the carnival as Death let out a musical laugh and pulled him along, running eagerly as her fingers intertwined with his.

"So, what first? Food? Rides? Games?" he asked, unable to keep the smile from his face at Death's wide-eyed excitement "The concert isn't until six, so we have a few hours."

"Hmmmm, food." She decides before giving him a playful grin "Then you are going to start winning me some prizes mister."

"As you command, oh great one." He said sarcastically, giving a dramatic bow only to yelp when Death pinched his ass.

"Great one? Oh, I like that. Now come mortal, I want a corndog and funnel cake." Still red in the face he lets her drag him over to a food stand. It was only after they got their food did he realize that letting his energetic and flirty girlfriend have a corndog as her food was not a good way to help his blush go down. Walking about they went to different attractions and games, Death rewarding him with a kiss for every prize he won, the bigger the prize the bigger the kiss. With such encouragement he quickly learned the tricks to any game where Death wanted a prize.

More than once some guy had tried to hit on Death, regardless of whether he was there, but each time she just laughed uproariously at their attempts like it was the funniest joke in the world. He had never seen anything emasculate a person worse and like a train wreck he could look away.

After several rides, some more food, and winning so many prizes they had to let the ticket office hold onto them in a room till they left they two finally made their way to the concert. Excited, Death climbs up and sits on his shoulders as she laughs exuberantly at all the hype for the coming concert. If anything, dating Death was never boring.

AN: As you can see, Ruby is an introvert, Winter is an Ambivert, and Death is an extrovert. So once more, tell me which path you like and why. I'll have made my decision by next time.