It's a joke, at first. Kind of.
Stiles had maybe been rambling on for a little too long about how Derek got a shit deal, but, first of all, it was all true. Second, Scott should maybe have been a little more understanding, considering just how many hours of mooning Stiles has to sit through every time Scott meets “the one”. Which is often.
Long story short, Scott got a little snappish and asked “why don't you just send him some flowers or something, jeez!”
And. Well. Flowers are nice, right? Right.
Stiles totally expects said flowers to be tossed directly in the trash, because in hindsight he decides that Derek doesn't really seem like a flowers and chocolate sort of person. But at the next pack meeting Stiles damn near falls on his face, because there on the counter is a fat, little vase holding the small, mixed bouquet that Stiles picked from the website. Sent anonymously, of course, because Stiles likes his limbs where they are, thanks.
And not only that, Derek looks at it and smiles every time he passes it, and brushes off any questions from the pack with a shrug. And a smile. So many smiles. Stiles feels a little overwhelmed with it, frankly.
After that, it becomes a mission. Mission: Be Nice To Derek Hale. And Stiles never does anything half-way.
He strikes up conversation with every single little ol' lady he can find, making sure to turn the topic of conversation to that nice young man Derek Hale, who Stiles totally saw carry Ethel's groceries the other day, and he definitely heard Gladys say that Derek rescued her kitty from a tree. He tells kids that if they see a big black dog in the preserve that it's super friendly, and loves belly rubs. He arranges for an entire troop of girl scouts to be carted out to Derek's new house, built a few hundred yards from the ruins of the old one, and, predictably, Derek buys everything they try to sell him.
The pack is fed Thin Mints for months. No one is upset about this.
And, on top of all that, Stiles keeps sending him flowers. Sometimes for totally valid reasons like his father's birthday or that he had his soccer mom car washed, but also sometimes just because. There's almost always a new bouquet on display at every pack meeting, and Derek obviously enjoys them, because Stiles happened to see him at the flower shop, asking how to care for bouquets so they'll last longer. It makes something warm and gooey go on in Stiles' gut, but he tries not to look too closely at it. If Lydia Martin taught him anything, it was that getting your hopes up too high lead to painful disappointment.
At Halloween Stiles bugs Derek until he buys ten times as much candy as he ever gets to give out, seeing as his house is quite a long way out. And he maybe makes it sound like it's because he wants to eat it all. Which he does, but he also makes sure to have Derek's house put on the list of destinations welcoming kids from the children's ward at the hospital, who get driven around in groups if they're well enough to go trick or treating.
Derek has pictures of every single kid who came to his door, and shows them off at the next pack meeting when they polish off the surprisingly small bowl of leftovers. Stiles damn near croaks from how cute it is.
Stiles sends Derek flowers on Christmas and New Year, and then an extra one in between because Derek had to be a Christmas baby, and have a birthday too.
It's only at Valentine's Day that Stiles hesitates, finger hovering over the mouse pad, ready to order a bunch of red roses. He's been taking a few odd jobs here and there to supplement his allowance to even afford spoiling Derek like this, and maybe this is taking it a little far. It's not like he has... like... intentions. Is it?
As good as he is at deluding himself, he's not quite dumb enough to try and claim that he wouldn't be over the fucking moon if Derek was struck by sudden insanity and decided he wanted to date a barely legal high school student whose company is tolerable only very occasionally. But to go from there to make it an actual goal? Stiles isn't masochistic enough for that.
He makes it tulips instead. They're cheaper, anyway. He maybe shouldn't have added the chocolates and the “Be mine, Valentine?” card. But no one said he had any significant sense of self-preservation.
Derek acts a little weird and closed off after that, and Stiles curses himself for being an idiot. Of course Derek wouldn't appreciate any weird and creepy secret admirers after his abysmal dating history, ugh. Stiles punishes himself by volunteering to do filing at the sheriff's station, a job literally no one wants. But it's as good an opportunity as any to spread some more barely-true rumors about Derek's excellent character to anyone who stands still long enough.
Only flaw in this plan is that Stiles' dad works there, and somehow Stiles manages to overlook that fact for long enough that certain suspicions arise, and Stiles only barely averts The Talk: Gay Edition by virtue of vehement denial.
He keeps sending Derek flowers, though. It's almost habit by now. His calendar is full of special Hale days, and also a few notes on which flowers Derek seems to like most, reserving those for extra nice occasions.
He's looking through college acceptance letters with the others in Derek's living room when shit hits the fan. His phone goes off, and it's an unfamiliar number, so he just answers it, not really paying much attention.
“Hello, Sir, I'm calling from Flower Power Delivery Online, I'm afraid there's been something of a mix-up with your latest order-”
Stiles panics. He's not proud of it, but he does. And so he does the only thing he can think of, and hangs up. Which means there's no way of saving it, and now he has six werewolves openly staring at him, because of course they heard everything.
Derek doesn't even have to tell them all to leave. They scurry away in a flurry of movement, scooping up their things, and literally running for the door, leaving Stiles alone and pretty sure he's about to face significant pain of one kind or the other.
“So, it was you,” is what Derek says. Because he's not an idiot, so of course he suspected.
Stiles isn't dumb enough to try and deny anything, even if he can't make himself face Derek. “Yeah. Look, I don't... I didn't do it for... you don't have to... do anything.” Smooth.
Which, fair point. “Well, I guess it would be nice to know if I should never talk to you again. I'll stop sending you stuff, obviously, don't worry. ”
This makes Stiles feel brave enough, or confused enough, to finally turn around and face Derek, taking in the small frown of his magnificent eyebrows. “Be...cause it's weird? It is weird, isn't it? I mean, how many random teenagers send you flowers and chocolate and dumb cards on Valentine's Day? It can't be much of a norm for anyone, so by sheer logic it would be weird, right?”
Derek snorts. “You're hardly some random person, Stiles.”
“Which kinda makes it even worse!” Stiles sputters. “This makes things super awkward!”
There's that frown again. “How?”
“How?!” Stiles flails helplessly, because he hardly knows where to start. But he stops when Derek steps closer, and catches both of his hands in his own. Stiles is still sitting on the couch, and Derek is just standing there, holding his hands, and doing nothing. It's driving Stiles a little crazy, and he looks up, confused. “What... what do you want me to do?”
Derek sits down on the coffee table, because he's weirdly uncultured like that, and gently squeezes Stiles' fingers. “Well, you could start by putting your name on the flowers in the future, so I know who to thank.”
Stiles can feel his jaw drop, but there's nothing he can do about it, because it sounded distinctly like Derek wanted him to keep sending flowers. And to admit to it.
“Uhhh. I... I can do that. Sure, I can do that.”
“And also please stop telling everyone I rescue cats. Myrtle keeps calling me every two days to get Tiddles out of her fucking oak.”
Stiles snorts out a laugh before he can stop it, but it's okay, because Derek is grinning at him, and Stiles is so very confused, because what is even going on here. “I'll keep that in mind.”
Quiet descends after that, and it's both weird and not weird to sit there in Derek's sun-drenched living room, holding hands, and smiling at the carpet. He kinda doesn't want it to end. But it has to, he's aware, and inevitably he also starts to fidget.
“So,” Derek mimics, because of course he does.
“Asshole,” Stiles mutters, but it comes out more fond than accusing. “So, what, uh... where does this leave... us?” He feels weird saying there's an us, but there is. Stiles isn't stupid, he knows they have a unique sort of relationship. They're pack, but Stiles is not a beta. They're close, but not really friends. And they've saved each other's lives too many times to try and claim that they're nothing. But it's still a pretty long way from casual flower giving and laser focused do-goodery.
For the first time Derek seems hesitant, and he avoids Stiles' eyes for a long moment. “Well. I guess that depends.”
“On what?” Stiles is on the edge of his seat, here, he's not gonna lie.
“On... whether you meant it.”
Stiles narrows his eyes, suddenly cautious. “Meant what?”
Derek sighs, and lets go of Stiles' hands so he can reach into his back pocket for his wallet. From which he then pulls that very same tiny card from Valentine's Day, the thick paper a little creased from being carried around, and the pale blue letters still asking “Be Mine, Valentine?” in swirly loops. Stiles feels a little faint, honestly.
“And... if I did?” he asks, weakly, and tries to remember how to breathe when Derek gently puts the card back into his wallet.
“If you did... then I guess the answer would be yes,” Derek says, casual in an obviously forced way, and Stiles has to clasp his hands together to stop them from shaking.
“Okay,” he says, and Derek huffs softly, a smile crinkling his eyes.
“Okay,” Derek says back, because he's really kind of an asshole like that. Good thing Stiles likes his asshole ways.
Stiles ends up sending a lot more flowers. And dumb little gifts. And he makes sure to add mushy and adoring message to every single one. And Derek tucks them all away in a box under his bed, because he's made of fluff inside, it's not even remotely a secret anymore.
And Stiles gets The Talk again. But it's okay, because Derek gets it too, and nothing screams love and devotion like sitting through the most awkward twenty minutes possible with your boyfriend and father in law talking about condoms, so Stiles doesn't really think things could have turned out better.