#undertaker's is a little shitty but i got worried that it was too short lol

[magicalara]

A Date to Amaze

"How would Grelle, Sebas, William, and Undie plan a first date with a fem (or gn) reader 🤔" requested by the lovely @cafeguaba-blog

I hope you enjoy and thank you for requesting!!

Includes: Grelle Sutcliff, Sebastian Michaelis, William T Spears, Undertaker x gn reader

TW: none :)

❤ Grelle Sutcliff ❤

- When Grelle goes to plan your first date with her, she’s almost shaking thinking about it. Not necessarily out of nervousness, though the feeling is present, but more out of excitement. She is purely just…excited to be able to go out with you after having had feelings for you for so long.

-  We’ve seen her crush on William, that thing has been around practically since they first met; can you just imagine how long she waits before properly making a move on you?? Sure, there’s the flirting and subtle innuendos (with consent, she does make sure you’re okay with them first) that she makes, but like, that’s because it’s Grelle Sutcliff. If she isn’t flirting in some way or form at least once a day then there is something wrong.

-  But this?? No, this is special, and Grelle will make sure that you feel how much she really does care for you even if it kills her

- She knows that there’s that little niggling feeling of doubt that comes with her having a romantic interest in someone, what with the way she always talks about her dear Bassy and William and all. As such, she wants to be able to solidify that you are the only person in her sights. 

- Grelle has the absolute urge to go all out for your first date, extravagance is her forte, after all. However, she also knows that “above and beyond” isn’t the best approach to this. So instead of the super fancy and expensive dinner and best seats to the latest show at the theater, Grelle plans a nice dinner at a little hole-in-the-wall place she frequents when she’s out reaping.

- She still shows up at your doorstep with the nicest bunch of roses that she can find, and pays for dinner, and even walks you home afterwards, but she tries to keep the extravagance to a minimum. Grelle knows she doesn’t have to be dramatic around you, she can be the calmer, more real version of herself that she usually keeps hidden. 

- Towards the end of the night, as you both walk with your fingers interlocked and hands swaying slightly between you two, she realizes how nice it was to be able to just be…herself. Not the fabulous Grelle Sutcliff, red reaper, but just Grelle (though she most definitely is still fabulous)

- And if you end the date with the offer to cuddle up on the couch with some tea or wine or coffee, well, who is she to say no?

👿 Sebastian Michaelis 👿

-  Is Sebastian capable of love?? Let’s ask that question first. /j

- No, but in all seriousness, if you’ve managed to capture the heart of this demon, props to you because whew boy. Sebastian doesn’t just like someone, he doesn’t harbor little crushes, no. When Sebastian falls for you, he falls for you. You are all that he thinks about whenever he allows his mind to wander and as much as he might will himself to stop at first, he just can’t.

- And so he does the only thing he knows- he asks you out on a date. He thinks that it will be a cure-all to get rid of his feelings, but uh yeah no, that’s not how that works, silly demon. Our Sebas doesn’t know any better, though, and so, in his mind, a perfect date will get you out of his head and won’t cause any long-term issues.

- Let’s be honest here- anything Sebastian does will be perfect because that’s just how he is. But this date?? Oh, honey, he goes above and beyond to make sure everything’s extra perfect. He doesn’t want to get too far away from Ciel so your date will have to be on the grounds of the manor but he makes sure that everything is still as amazing as it would have been if you guys were somewhere else.

- Sebastian plans a nice picnic out in the gardens for the two of you to enjoy around sunset. Living in such a secluded area does have its perks, after all, and the sunsets are most definitely one of those perks. Sebastian knows a perfect section where you can just see the land stretch out as the colors of the sky are painted before your eyes.

- He admires your features as you admire the sky and, as it gets darker and darker, realizes that he really was in love and there was no way he could rid you from his mind or heart; no, you were there to stay. And so, once the sky was dark enough where he knew it was safer to bring you inside, Sebastian grabs your hand and does just that, promising a warm cup of tea and an even better view of the night sky from above.

- Your night ends with you leaned up against his side next to a window as he tells you stories of the stars and all the endless possibilities they hold, the demon next to you completely and utterly enthralled with how such a rough being such as himself could possibly deserve the angel next to him.

👓 William T Spears 👓

- William T Spears is a busy man who has no time for such frivolous activities like dating…right? That’s what he, as well as everyone else in the office, thought.

- But then, here you were, a member of the library staff, not only just as enthralled by reaper history as he is, but even more so enthralled by reaper history. Sure, he knew his quick facts here and there, but never did he think he’d be able to find someone who could practically recite every history book cover to cover.

- And that’s just the tip of the iceberg as to why William is absolutely captivated by you; you’re also amazingly sweet and nice to everyone, have really funny jokes, actually do your work, and are just captivatingly beautiful. It also helps that you work in the library bc that’s his favorite place and he has a thing for librarians 

- Anyways, because it’s been so long since Will’s thought of anything romantic, he doesn’t really know how to ask you out. So what does he do? Make what was, in his mind, not a very good decision at first. He went and asked the one guy he knew who knew everything about dating: Ronald Knox.

- Ronald’s shocked at first because William T Spears??? dating??? It’s a miracle y’all. But once the teasing went down, Ronald gets to business asking everything that Will knows so that he can help make sure this date is successful. He’ll even go in and be a wingman to his senior if need be.

- They find out your favorite flowers, drinks, food, activities, any and everything they need to. The best course of action seems to be a new exhibit at a museum that you took an interest in recently but haven’t had much time to visit. So when it comes time to ask you out, William shows up at the end of your shift with a small bouquet of your favorite flowers and a proposition to go to the museum and maybe stop by a cafe afterwards if time permits. He’s all nervous on the inside, but is very good at hiding it.

- Obviously, you accept and the date goes just amazing. Both of you thoroughly enjoyed the exhibit with all it had to offer. William definitely did that thing where he just stands back and watches you as you get all excited with a small smile on his face.

- No kisses happen at the end once he’s brought you back to your apartment (he is a proper gentleman after all), but he does give you a hug goodbye and watches as he makes sure you get inside.

- Ronald hounds him the day after wanting to know how it went and bragging that of course it went well because William had the expert Knox on his side. William gives him overtime for the comment afterwards

💀 Undertaker 💀

- It had been so long since Undertaker had had someone who he thought of in such a way with such a strong prospect of it going well that he almost surprises himself at how happy he is whenever you end up walking into his shop. One thing’s for sure, though: he doesn’t want to mess this up.

- Undertaker knows he isn’t the best partner in the world, he runs an underground necromancy ring for heaven’s sake. But what he is good at is being romantic so his first date with you will be as romantic in his little way that he can make it. 

- He doesn’t really leave the shop very much (definitely not for dates, at least) so for your first date, he plans to take you stargazing on the roof. He bakes his little treats and makes that really good tea that he only saves for special occasions. There’s even an old telescope he drags out of his storage so you can see the sky better. 

- It’s a beautiful night out, but Undertaker definitely says that you’re more beautiful than all the stars in the sky. Wraps his arms around you from behind and sways as you just gaze out at the sky, humming any random tune that comes to his mind.

- Just lots of soft, whispered affection. Undertaker doesn’t really do the whole “date first, relationship later” thing, y’all are already together I probably should have mentioned that first oops. But basically, when he finds someone that won’t leave his mind and they aren’t leaving physically, Undertaker doesn’t waste time. Sure, he has all the time in the world, but he is all too aware of the fact that you don’t. 

- So he’ll spend as much time as he can giving you affection and showing his love for you, this “first date” is no exception to that rule. Undertaker is a romantic, but he also doesn’t do those huge grand gestures to show it; these moments under the stars are all that he needs.

- The date ends with him insisting that you stay over as it’s much too late for you to go home now and “No lady should be out wandering late at night lest they get into some sort of issues, especially when they’re as pretty and precious as you, m’dear.”