50 First Dates, but it's HiJack (FrostCup, Jackycup)
Hiccup is a marine veterinarian (who works alongside Fishlegs, Astrid, Snotlout, and the twins). Jack is a figure skater with short-term memory loss (though he believes he is on a break after winning the finals, when in reality he was forced to retire when it became evident he would be unable to continue competing after a terrible accident).
Hiccup meets Jack by chance at a restaurant Astrid and Fishlegs recommended for its good food and friendly service, and he thinks they hit it off. It's the happiest he's felt since he and Astrid split up. They agree to meet at the same time tomorrow at the same restaurant. Unfortunately, the next time they met, it didn't go how Hiccup thought it would. For one, Jack has no idea who Hiccup is, and even worse, there was a BIG misunderstanding when the marine veterinarian brought up the walrus he named Toothless.
The waitress, who turns out to be Jack's cousin, Sophie, tells Hiccup about how Jack forgets everything each night due to a brain injury, forcing him to relive the same day over and over.
Not one to give up (and hopelessly optimistic that maybe one day Jack might remember something about him, even if it's a sort of deja vu moment), Hiccup visits the restaurant every day after work trying to woo the white-haired man and win his affection anew. Some days are great, and they hit it off like the first time; others he completely drops the ball and looks like the pining idiot he is (though sometimes Jack finds that cute), and on occasion Jack wants nothing to do with him at all (one day the man even pretended he could only speak another language that Hiccup did not even know the name of. That day hurt a little more than the others, but he still showed up the next day, ready to try again).
Jamie, the restaurants chef, even tries to chase Hiccup off the day after learning about the memory loss of this because whatever reason Hiccup has to woo his forgetful cousin day after day can't be for anything good (he thinks the man wants to get in his cousins pants and thinks he can up and leave one day with no consequences. No, sir, not on his watch!). When he learns that Hiccup hopes Jack will one day remember some part of him, Jamie tells him that his cousin has been like this for 3 years, and their family and friends have tried the very same thing with no success. Hiccup takes one look at Jack, who is laughing at something Sophie said, and declares he still wants to try.
Jamie thinks the one-legged man is delusional (and finds him a little sad since it's obvious he's falling for a man who forgets he exists every day) and decides to make a deal with him. Hiccup has to order one item from the menu, something that is at least over 10$, for each day he is at the restaurant. If he can win his cousin's affection that day, his order will be half off. But if he fails, he pays double.
After 3 weeks of this, Hiccup meets the rest of Jack's family. There is Aster, who seems like a rather reluctant honorary uncle; his sister Emily, who was his figure skating partner; and North, who has been taking care of the Overlands since their mother's passing. It was a rather terrifying conversation, considering two of them came off as joyful and friendly at first. They explained the accident that happened, how hard the beginning had been for Jack when every day he woke up to learn what he had lost and missed, and how much it hurt to watch. Then how they came up with the idea of simply repeating that day's events as best they could. Jack didn't get hurt unless it was a "bad day," and with Berks weather being mostly the same for 9 months of the year, it was rather believable to pretend it was still January.
North spoke about how Jamie and his sister told them about Hiccup, and how, even though Jack forgets him every day, he still tries to win the man's affection and hopes that he will be remembered in some way.
"I do not think he remembers, but part of him is happy when he sees you. Those days, he is happiest I have seen in long time." "Usually when he skates, he thinks about upcoming competitions, different choreographies, and possible songs for us. But ever since meeting you, he skates because he WANTS to, sometimes even singing when he does. And when the ice is melted, he DANCES! Jack doesn't dance! But something about you makes him want to." "I reckon the frostbite has been a bit calmer since meeting ya. Not as many pranks and my paints don't go missin'. Despite the odd situation you both are in, you seem like a good bloke. The fair dinkum, yeah? But if you hurt 'im, in any way, I'll put ya 6 feet under."
One day, Jack gets a ticket for out-of-date plates. Hiccup watches as Jack discovers he has been living the same day for the past few years. He joins Jack and his family on a trip to a big-name hospital in Bergus (a town that's an hour drive from Berk), where Jack learns from a doctor he can't remember about the accident that put him in a 3-month coma and permanently ended his career as a figure skater.
Hiccup watches as Jack asks how many times this has happened (almost once a month), if his sister still competes even if he's not there (a lot more recently), if Asters decorative eggs are selling better or worse (about the same, though they're more popular around Easter), and if North has any new toys the kids are going crazy for (the most popular is this little robot Phil designed). Jack asks about Hiccup as well. How many times has he been to the hospital with Jack, how Hiccup's first meeting went, and why he still keeps trying even when he knows Jack won't remember him the next day.
"Do you do something different every day?" "Always. Though there have been a couple of days when you want nothing to do with me or turn me down." "Well, at least I'm unpredictable."
When the day ends, Hiccup reflects on the day's events and how hurt Jack had been not only by the accident and the time lost, but also by the fact that he had been living the same day over and over again.
"I get why they do it, but that doesn't make it any easier when it goes like this. A day that I find out it's all a lie, and that by tomorrow morning, it will start up again like today never happened. It will continue until there's another day just like this one where it throws everything out the window... at least this is the first time you're here." "What if tomorrow isn't the same? What if they told you about all of it?" "... At least it wouldn't be a lie."
The next day, Jack remembers none of it.
"Do you have a favorite flower?" "Why? You plan on taking me on a date, handsome?" "If you'll have me." "Hmm... Crocuses. The purple ones." "I'll bring you a dozen."
With Jamie and Sophie's help, as well as Fishlegs, Hiccup delivers Jack a dozen purple crocuses and a tape. The tape tells Jack about the accident and his recovery; how it ended his career. It also tells him what he missed. Aster has been able to sell his decorative eggs online, Sophie is attending university online, North's shop has gone international, Jamie has become chief of Berk (just kidding, Stoick the Vast is still going strong, but Jamie's culinary skills has improved greatly and his mom says the family business will be in great hands after she retires), and Emily was able to get to the semi finals last year. Hiccup talks throughout the video, telling Jack about what he's missed and asking everyone what they want Jack to know.
"How many times have I seen this?" "This is first time."
And then it would go on to Hiccup taking Jack on a bunch of first dates and all that stuff I'm not good at writing about. Maybe even go similar to the movie, and they split for a bit (can't remember what happened, been a while since I've seen it), and when Hiccup sees North or Emily, one of them hints at Jack remembering Hiccup. When he realizes it, he visits Jack and learns that he dreams of him, but he can never place a name to the face. He tries to draw the one-legged man, but he's not Aster, so they don't come out right. He still tries because he doesn't want to forget. Then it ends with a time skip, with Jack waking up to watch an updated tape of everything: his wedding, and clips of him and Hiccup adopting two kids and watching them grow. When he leaves the room, he meets his kids, a 7-year-old girl and a 5-year-old boy, as well as the man he married.
