AN: We're going to have a nice little date before things to got hell in the next few chapters. Enjoy!

Disclaimer: I do not own Helluva Boss. Spiroz, Milton, and Mitzy are characters that belong to DaniDraws who I have permission to use for this fic. Hedwig and her family are my original characters.

He had a girlfriend.

Sprioz had a girlfriend.

He still couldn't believe that even though it had been five days since he confessed his feelings to Hedwig. The two of them had only met twice since then to hang out in the forest, curl up with each other, and occasionally kiss while talking about their day. They greeted and said their farewells with an "I love you," which made Spiroz realize just how special those three words he always heard his parents speak to each other. Other times they just texted each other, talking about their actions and how their siblings teased them.

Apparently, it was a big sibling obligation to make fun of your younger sibling when they had a special someone. Spiroz was still surprised that Hedwig's parents were happy she was with someone she loved. Her mother had only been worried about them being too closely related when she heard he was a Goetia, only to relax upon seeing how far they were from the family tree and that they didn't need to worry about fears of incest.

Of course, the only thing they had yet to do was go on an official first date. While technically they did always hang around each other (Which their siblings teased as "pre-dates"), they were doing that as friends. Now that they were officially a couple, they had to have their first romantic evening together, and Spiroz had been the first to suggest it only yesterday. Hedwig happily said she would love to go on a date Friday evening (A safe time for Spiroz since his parents would both be out that night).

There was only one problem that Spiroz had: He had no idea what to do for a date.

Before Hedwig, Spiroz never dreamed he would find someone he would fall in love with. He had several crushes on a few girls before growing up, but those died out when they acted mean or ignored him because of who he was. So he dropped the hope of finding romance together until now. He needs to know what to do for a date, what to wear, and what to do after it.

His parents were out of the question due to them not knowing Spiroz's girlfriend was an angel. Knowing his Dads, they would suggest something embarrassing or lewd, especially since his Imp-Dad had no shame whatsoever. He also couldn't go to Aunt Millie and Uncle Moxxie because he was sure they would tell his parents about Hedwig. The twins were too young to date (according to their parents), and they were just as clueless in romance. And Loona? Her record of disastrous relationships with her numerous boyfriends speaks for itself.

That left his older sister, Octavia.

"Spiro, you need to calm down. Pacing around isn't going to do anything but make you cramp out your legs," Octavia said as she sat on her younger brother's bed. The Imp-Owl hybrid couldn't stop moving or biting his fingers as he tried to think of what to do for his first date with Hedwig. "You're going on your first date. Not getting ready to go to war."

"But the first date is always important! It has to be memorable! Something we can remember for the rest of our lives!" Spiroz pointed out as he rubbed his head with both hands. "Should we go to France? We could kiss on the Eiffel Tower. Maybe Spain? We can go to a nice paella restaurant. Italy is a romantic place. I just need to avoid getting too close to the Vatican, or I'll burst into flames. Or we could visit the moon! Picnic on the dark side of Luna! Romantic, right?!"

"First off, take a deep breath," Octavia said, grabbing him by the shoulders and getting him to slowly calm down by rubbing them. He took a few deep breaths and nodded. "Good. Now tell me. Is Hedwig the kind of girl who would be impressed by any of that?"

"...No," Spiroz sighed as he began to sulk. "She already lives in Heaven, for crying out loud. Plus, her family visited Earth so often it wouldn't be a romantic area."

"So show her someplace she's never seen before, but you have. A special place that means so much to you that you want to share it with her," Ocavia said as she giggled. "That's what Samual did for me when we dated. He took me to the Ring of Envy, and we had our first date on the beach by the Sea of Desire. His parents proposed there, and every year on their anniversary, they would take him there to play and have fun growing up. It symbolized something important in his family, and Samual took me there to show he wanted me to be part of that life."

She winked at him and nudged at the various star constellations glowing in his room. "Can you think of any place special? Maybe in a certain area, Dad always took us when we couldn't sleep?"

"Oh... oh!" Spiroz gasped as he looked at his sister with beaming eyes. "How could I have forgotten there?! Dad used to take us there all the time and sing to us, and we would watch the stars and comets. It's perfect! I can even do the whole picnic thing I mentioned earlier!"

"Yup, but maybe it's best to let the servants make the food," Octavia giggled. "Don't want you to burn down the kitchen again?"

Blushing, Spiroz huffed. "That was one time, and I was ten."

Meanwhile, a particular snow owl angel was dealing with the worst thing that could happen to a girl before she could go on her date: not knowing what she would wear.

"What do I wear?! What do I wear?! What do I wear?!" Hedwig screamed as she ran from her room to the living room, where her family watched the panicking white feathered angel act like a headless chicken. "What about this?! No, too flashy! Or this?! No! I look like a prostitute! How about this?! Gah! What am I thinking?! It's too 1970s!"

"We are so showing this to her future kids," Elladan whispered to his nodding twin while filming the whole thing on his phone.

"Dear, you're going on your first date. Not meeting the Archangel Gabriel," Zenikel chuckled as his daughter continued to fly in and out of the room with dozens of outfits. "I think you need to calm down before you worry yourself to death."

"If that happens, we can solve her clothing problem by putting her in a funeral dress," Elrohir joked as he high-fived his twin.

Hedwig threw her blouse and shorts at the two and glared at them. "Oh, like you two never panicked for a date before."

"We haven't," Elrohir said with a grin.

"Because unlike you," Elladan continued with a smirk.

"We're always in control of ourselves," The twins both said as they winked with an opposite eye each.

"I am so in control of myself!" Hedwig huffed as she put her hands on her hips.

"Didn't you completely go into Demon-Fan-Girl mode when you first met Sprio?" Elladan pointed out.

"And checked out his butt so you can see his tail feathers to determine what kind of bird demon he was?" Elrohir asked, which made Hedwig shut up and blush.

"Boys? Enough teasing your sister."

A figure got up and moved towards her daughter while she smiled thankfully at her mother for keeping her annoying twin brothers at bay. Zara Illuminus, formerly Zara Goetia, was such an angelic figure that you'd be surprised to learn she was once a demon.

Most of the looks from her kids came from her, as she was a snow owl like them but with traits of red on the tips of her feathers and purple spots instead of black. Her eyes were a dark gray yet shined like twilight in the night while her white-tish blond feathered hair flowed down like a waterfall to the middle of her back. Her cheeks were thin, and her beak was bright yet dark as night. She was the tallest out of all the angels in the room, which wasn't a surprise as the Goetia Family was known to be very big, and some demonic bloodline traits could not be removed even if you became an angel. She wore a white velvet sundress with black and white sandals and a silver diamond cross around her neck that was on the right side and not the wrong side like she used to wear in her old life.

Zara placed her hands on Hedwig and looked at her with a warm smile. "Sweetie, you need to relax. You're almost as bad as your father was when he was getting ready for our first date."

"I wasn't that bad," Zenikel muttered while hiding the blush on his feathered cheek.

"No, you were worse because your parents told me that you practically were ready to hide in Las Vegas under a new name to save the embarrassment of what you thought was going to be a screwed-up date because you filled half your clothes with sweat before you rented something," Zara teased which made Zenikel grumble as his sons laughed at this information.

Turning back to Hedwig, Zara continued, "Hedwig, you just need to go with what you think is right. Sprio is a Goetia, and if he's anything like his father, Stolas, he will dress up in a ravishing outfit for his first date to impress you. His side of the Goetia family tends to go all out on outfits for special occasions."

"So, should I also dress in something similar?" Hedwig asked, tilting her head.

"Hmm, yes, but it should be in your style that screams you," Zara said as she waved her hand. "Something that makes you, excuse the pun, look luminous before him. Think of him as the moon, and you are the star that will shine beside him. Something bold that will make you stand out yet has enough of your desire to be with him as an equal partner."

"Hmm," Hedwig thought long and hard for a second before snapping her fingers. "I got it! Wait one moment!"

It took nearly twenty minutes, but when Hedwig came out with the dress she thought best fitted her, nobody could deny that she looked beautiful. Her brothers could not make fun of her as they were also stunned. The dress that Hedwig had chosen, extending down to her heels, was a light ocean blue color with moving mystical waves flowing through the silk as if it was the actual sea itself. It moved with her, changing the direction of the waves with each movement. The center chest area was covered by a pure white blouse with sparkling diamonds that formed into the design of two angel wings spreading out. Her feet came with matching heel shoes that shined white with sparkles that clicked with each step.

"W-W-Well?" Hedwig asked, turning around with a slight spin. "This good?"

"Sweetie, you look like a true beautiful woman," Zenikel whispered with pride as he walked over and kissed his daughter on the cheek. "If Spiro doesn't think you look like a true beauty? He's blind."

"I think you made the right choice," Zara said with a wink.

"Eh, it's okay," The twins said, but it was clear that they were impressed by their looks.

"Okay. Then all I need is some makeup, and I'll be ready for tonight!" Hedwig said with glee before panicking. "Oh no, I don't know anything about demonic dating customs! I never researched too deeply into that before! I still got some time! I can just quickly study and-"

"Hedwig? Breath," Zara commanded, and her daughter did so. She took a few more just to be sure. "Don't worry about such things. Focus on just enjoying yourself. But before we do your hair and makeup, I have another thing for you."

Zara approached the coffee table, where a small black and silver decorated box was laid out. She opened it, revealing a sapphire-stoned pentagram necklace right side up instead of upside down. The stones of the sapphire pentagram necklace had magical essence swirling inside of it that one could sense it.

Contrary to popular belief, the pentagram was not seen as an unholy symbol in general, as it had been used in early Christianity as a symbol for the five senses or of the five wounds of Christ. It was only when it was upside down that it was seen as wrong, similar to how Satanists reversed the cross to insult Christ.

Confused, Hedwig watched as her mother pulled it out and looked at it with nostalgia. "This necklace was given to me by your grandmother when I went on my first date when I was sixteen. She told me that everyone in her family with a daughter always gave it away on her first date. It was practically the only thing I kept and was allowed to keep after my redemption. My mother was the only one who silently encouraged me to go to Heaven when the rest of my family disowned me."

With a slight tearing in her eyes, Zara gently put it around her daughter's neck and smiled. "Now I'm going to give it to you. And I hope you have a daughter you will give it to someday on her first date."

Hedwig smiled back at her mother and wrapped her arms around her before hugging her tight. The mother and daughter nuzzled each other cheek to cheek before the former nodded. "Right, now let's get your makeup done. Sorry boys, but this is a girls-only part."

The two females giggled as they walked back to Hedwig's room while Zenikel shrugged and chuckled. "Alright, boys. Let's get some cold ones and leave the ladies to do their thing."

"We're not going to sit around waiting for Hedwig to return from her date?" Elrohir asked.

"Nope, but we are going to plan various revenge plans if he hurts her in any shape or form," Zenikel said with a wink. "Just in case."

"Now that I'm down for," Elladan said with a grin.

Spiroz had long ago decided what he wanted to wear for his first date. The same outfit that his father used for his first date. Technically, there were two "First Dates" regarding the relationship between Sprioz's fathers. Not long after the Fizzarolli incident, everyone told Spiroz, Mitzy, and Milton about the tragic first one. Blitzo admitted he had used Stolas to spy on Millie and Moxxie on their anniversary instead of taking Stolas out as the Prince thought. That led to their embarrassment, misunderstanding, and Blitzo's attempted suicide after a mental and emotional breakdown. After Blitzo finally got the help he needed and things slowly cleared up, Blitzo asked Stolas for a proper first date, and Stolas wore the same outfit as before. That one turned out to be a marvelous one that finally started their romance, leading to their marriage.

Occasionally, Sprioz's Owl-Father wore that outfit during important events like anniversaries or a private night. It was important to him, and he treasured that outfit very much. When he was a kid, Spiroz liked the outfit so much that he asked for a version of his own when he found his special someone. Granted, Sprioz soon gave up on romance after getting it, but he always kept it around. Now, the hybrid demon was happy he owned it. He did need to use a few growth and extension spells on the clothing to make sure it fit him at his current size, but Octavia said he was the spitting image of their father.

He waited by their usual spot in the human world, fiddling with his hands as the cool night wind blew through the trees. Octavia said she would set everything up for him at the realm where he had planned his first date and hoped that everything would be perfect for the evening. Please, God or Satan or even both, let this night go well.

A few moments later, a white and blue heavenly portal opened up, causing Spiroz to stand straight in preparation for Hedwig. The moment he saw what Hedwig was wearing, his eyes lit up, his tail went straight, and his mouth dropped. Hedwig wasn't just beautiful. She was drop-dead gorgeous. Her dress wasn't just amazing, but her face was well. Her combination of blush, eye lighter, and lipstick made him sweat from the cute look that was blushing as he continued to stare at her.

"W-Wow," Sprioz gulped before giving a nervous smile. "You look...amazing!"

"T-T-Thanks! You do, too," Hedwig whispered as she nodded her head.

The two stared at each other in silence, taking in the sight of each other before Spiroz coughed into his hand. "W-W-Well, are you ready?"

"Yes," Hedwig said with a nod before asking, "but where are we going for our date?"

"Well, it's not going to be here on Earth," Spiroz said as he walked closer and lifted one of his hands that were glowing. "We're going to a realm my family has had access to for generations. Most of the time, it's used for experiments, learning magic, or meditation, but we also use it for fun or relaxation. You'll be the first angel to come here, but don't worry. It won't harm you."

"Okay," Hedwig said as she slowly stepped forward and wrapped her arms around Spiroz. The hybrid demon blushed upon feeling her latch onto him while feeling the warm comfort of her wing wrap around his shoulder. "Um, I'm ready if you are."

"R-R-Right!" Spiroz replied as she opened his glowing palm, and a portal to the outer dimension appeared. He guided Hedwig through it, feeling her increase the pressure of her grip as he did so, but once they passed through, she gasped in wonder.

The velvet, ethereal sky was a wonder even for the angel who had lived in Heaven all her life as endless seas of stars and cosmic bodies glowed like sparkles on a diamond. The calm and gentle breeze of stardust and aura winds made their feathers tickle, while the burning blue and red moons created a warm purple light that guided them through the strange and mystical rocky terrain they landed on. Falling stars shined in Hedwig's beautiful blue eyes, and her smile was joyful as she laughed at such a sight.

"It's almost like the Empyrean," Hedwig whispered in awe as she twirled around to see it all better. "But it's also like simultaneously being in a planetarium and an alien world."

"Yeah, I always love coming here," Spiroz said as he guided her down the path. "I can still remember the first time my father brought me here when I was five. I couldn't sleep because of a scary dream, so he took me here, sang me to sleep, and I felt safer in his arms than I ever did in my covers."

"He sounds like a great man," Hedwig said with a giggle. "I hope one day I can meet him."

Spiroz's smile lessened a little. He hoped there would be a day his fathers could meet his girlfriend, but he knew it wasn't the right time. Hopefully, one day, but for now, it was not the time to think of such future possibilities and focus on the now. Seeing the objects placed in preparation for them already prepared, Sprioz took Hedwig by the arm and guided her toward their destination. "We're here. Dinner is served."

Hedwig stared at the fancy white diamond glass table with silverware all set for them and a cold bottle of sparkling water. A complete course meal, made from the best ingredients and cooked by the palace's best chefs, was there warm and ready for eating thanks to a preservation spell to keep it nice and hot.

Scallop salad with vinaigrette sauce.

Prawns in chili sauce made in canapé style.

Foie gras and flatfish decorated in a citrus sauce.

Sea eel royale with truffle sauce.

And sesame beef on top of white rice with teriyaki glaze.

All mouth watering for both as they quickly made for the table. Being the gentleman he was raised to be, Spiroz pulled the chair out for his lady and thanked him before sitting down. He soon took the sparkling water, popped the cork, and poured it for them both before sitting down. After a small cheer, they drank a bit before smiling at each other.

"This looks all so good. I can't wait to eat it," Hedwig said with a lick of her lips.

"Well, I hope you enjoy it with the show we're about to see," Spiroz replied with a grin.

"Show?"

Spiroz looked up towards the right, and Hedwig soon followed. Not long after doing so, the stars in the sky start to move and dance around as if they were fairies in the sky. Hedwig gasped as there were a series of colorful explosions like their rainbow light show. The sparkle and excitement in her expression made Spiroz equally as happy as he felt his worries about the date disappear as they continued to watch the show while engaging in their dinner.

The night went better than Spiroz could have hoped. They were still eating well after the show and had plenty to discuss. It was almost like one of their friendly hangouts before they became a couple, except there was a different feeling to them all. Something that made it feel more magical whenever Hedwig talked, and something in her eyes made him never want to look away. When the dinner was over, Spiroz opened the portal back to the forest on the mortal plane and guided her back to the spot they were before.

"Wow, I have to admit. I never expected such a great first date," Hedwig said with a giggle following afterward. "Glad we didn't have dessert because I'm stuffed."

"Dessert? Shoot!" Spiroz slapped his forehead and muttered to himself. "I can't believe I forgot that! Uh, you want to go to the Cheesecake Factory in town? I mean, we might be overdressed, but-"

Hedwig laughed and shook her head before lightly smacking Spiroz on the shoulder. "Relax, you silly-nilly. I just said I was stuffed. Besides, you made the date perfect as it is. But there is one thing that we can do to make it more perfect."

"What's that?" Spiroz asked.

"This."

Hedwig then grabbed Spiroz by the shoulders and slowly brought her lips to his. They touched beak to beak and slowly closed their eyes as they let the taste of each other's kiss fill their hearts with such passion that it was almost as if they were having a star show. Spiroz slowly wrapped his arms around Hedwig and hugged her closer, pushing a bit harder with his beak as he felt that he was genuinely starting to treasure.

Pure happiness.

Happiness that came from this one angel who he met by chance in these very woods and became his best friend to his girlfriend in only a few months. Her smile, kindness, and love had washed away years of darkness in his soul that he had been forced to carry thanks to his mere existence. Of all the things he treasures, Hedwig's love and caring heart was the one he valued the most in his life, and he would see to it that they never parted for any reason.

Well, save for the need to get air.

Ending the kiss, the young couple looked at each other, demonic red yes to angelic blue eyes, and smiled. Already they knew that they wanted to have a second date after this.

And many more to come.