I just had this really adorable idea: The S/O of Creampuff, Sweets, Axe and Red are going on holiday and give them a special cushion before they leave, and sewn on the inside of the cushion cover is a small pouch with an engagement ring in it and a note explaining that they're too nervous to do it in person but wanted to propose and so they're doing it this way.
Oh, you are tickling the best part of my brain right now with this fluffy ask. I love this so much, and I hope this works well!!
UT Papyrus/Creampuff: As much as he hates you leaving for a holiday, he’s got to admit that you probably need it at this point! Creampuff knows the signs of you being tired, and he’s well aware of how you crash without a good rest. This break is the best thing for you, even if he really wants to go with you and if he doesn’t want you to go. He’ll give you sad puppy looks the whole way to the airport, even as he proclaims loudly that you’ll do fine without him, not the other way around. Once you hand over the cushion, though, the moment you’re out of sight, he is going to open it, no hesitation. It takes all of seven seconds to read the note on the interior, then Creampuff takes a mad dash through the entire airport just to see you and tell you an enthusiastic acceptance. He won’t let you leave without at least one or two smooches before you get on.
“YOU CANNOT EXPECT ME TO NOT LOVE ON YOU AFTER THIS!! YOU ARE AMAZING AND WONDERFUL, AND I LOVE YOU SO MUCH!!!!”
HT Papyrus/Sweets: Of course, he knows that you’re working just as hard as he is and, in some cases, more than him! Sweets doesn’t want you to burn yourself out by overworking to the point of stress, so it’s highly likely he’s forcing you suggested that you take this vacation. He’ll gently push you to do well and keep checking in on you as needed while you pack, reminding you that this is time to not think about anything stressful. However, as you hand over the cushion, the skeleton will hold it carefully and ponder what’s inside. Unlike his counterpart, he waits until you’ve told him you safely arrived to ask about it over text. You can bet your absolute bottom dollar, though, that once Sweets has the pouch open that he’s calling you in near hysterics. He wanted to propose, but you’re just too dang cute and sweet, even if this proposal isn’t in person.
“Oh My Stars, You Shouldn’t Have Gotten Such A Nice Ring, It Must Have Been So Expensive, But I Love It And You So Much I Can Hardly Breathe!!!!”
HT Sans/Axe: This particular skeleton might actually forget that you’re going on vacation a few times until he sees you packing. There is an initial panic on Axe’s end that he did something stupid and you’re upset, but a quick reminder soothes his worries. The moment you leave, though, with the package delivered in full, he’s waiting for you to get back. The ironic thing about the cushion is that he won’t realize it has an openable compartment until either his brother points it out to him or until you get back. Even then, he’s hesitant to open it until he has your full permission, so once you confirm that no, it’s not something you’re taking back and yes, he can open it, Axe will gently pry it open. The very second he sees the ring, he knows exactly what the intention is, and you’ll have an elated but teary skeleton on your hands who won’t quit saying yes.
“oh, i was supposed to open it? whoops, sorry lamb chop, let me just... oh... oh. you... you really want to... to marry me..? i... you... uh... yes...”
UF Sans/Red: Normally, this boi would hate to have you sent off on your own without him or someone he trusts going along with, but you need a break. It’s not often that Red will swallow his pride and protectiveness for anyone’s sake, but you have a massive soft spot in his metaphorical heart. He’ll help you pack up your things, sort out any missing items, and then find a way to get you settled wherever your destination is. When you hand over the cushion, he’s concerned and confused, but he dutifully waits until you leave to open it. However, unlike all the skeletons on this list, Red almost panics. The entire time you’re gone is utter hell to him, and he’s a confused mess until you get back. Even though he doesn’t mean to come off as mean or angry, he will confront you about this. It’s not that he will say no, but he needs to hear it from you to know this is real.
“no, no, no, you have t’ say it... please, indulge me a lil’ sweetheart? i... i need t’ know that y’re serious ‘bout this cuz i don’t think i could handle y’ fakin’ this...”
Thanks for the ask, @nevergonnarollagain! (don’t know why it won’t tag...)