A/N: When I watched RTTE season 5, I was quite mad that we never saw how Hiccup proposed to Astrid (Or the other way around, who knows?). But then I realized that this gives us the opportunity to imagine our own versions, so this is mine. I already had it in mind long before season 4 even and in a way, it's a part of 'Astrid's Diary' but works as a stand-alone story as well. Here just a bit of background information:

In my headcanon (Astrid's Diary), Hiccup and Astrid have been a couple already long before 'Blindsided' but certain events led to them breaking up only to get back together in 'Blindsided'. The rest of the gang knew about it, but Astrid didn't know that they knew. So, for everyone's sake, they kept pretending to not know. But after the events of 'Shell Shocked', that's obviously not possible anymore...

. o O o .

„What are you going to do now?"

Hiccup flinched and turned around to look into Snotlout's disapproving face. He hadn't expected anyone to drop into his forge, not today!

"What do you mean?" he asked artlessly and turned back to his desk. Casually, he pushed the rough sketch he'd made just now beneath some loose papers, pretending to simply clean up his desk. He knew perfectly well what his cousin meant, had thought of little else for days now. And yet he had no answer. How could he have an answer?

"Astrid?" Snot prompted and Hiccup could hear the annoyance in the other boy's voice. Because they were just that, boys. No matter how mature he might feel and how much they all played grown-ups out here at Dragon's Edge, he didn't feel… ready for this. Sure, there was no doubt in him, but still…

"What are you going to do about her? You can't make us act as if we don't know about you two again. Not now that we caught you and she knows that we know." Hiccup sighed and rubbed his face. It would be so easy if they could go back to that state…

"I don't know, Snot! Okay? I just don't know! We can't openly announce to be a couple either. If we would still live on Berk, there wouldn't be a problem. But her parent would never agree to let her keep living here if they knew…" He explained agitatedly. It wasn't that easy anymore. Sure, everybody had suspected them to be a couple already, even longer than they'd actually been a couple, but still. Suspecting something or actually knowing it… those were two different things entirely.

"You're an idiot!" Snot declared as if it was the most obvious in the world.

"I-" Hiccup started but broke off immediately. Of course, Snot was right. Berk's rules for unmarried couples were strict but simple. He just wasn't sure whether he was ready for that step yet.

"Man… you're pathetic!" Snot stated flatly and gave him a matching glare. "But hey, keep brooding if you think that helps. Just remember, we plan to visit Berk in three weeks. And I won't pretend to think you two are just friends any longer. And neither will Fishface or the Twins for that matter. You might want to make up your mind until then" With these words, Snotlout left the forge again and left Hiccup in a despondent mood.

Because it was actually quite simple. An unmarried couple was allowed to slowly grow together, get accustomed to each other before any official arrangements would be made. But all this had to happen on Berk! Were the parents and literally everyone else could make sure they behaved. Kissing was allowed but that was it. Just kissing and nothing more. And he and Astrid had already done more. So much more… No, if they were to announce their relationship officially, Stoick and Astrid's parents had no choice but to keep at least one of them on Berk, if only to keep up propriety.

Berkians were a reasonable lot though. Arranging a wedding took time and not every couple was willing – or able – to wait that long. So a couple didn't need to actually be married to be allowed intimacy. They just needed to be betrothed. The later bride and groom just had to formally agree to get married, their parents had to give their consent and the bride price had to be paid. That was all.

It was so simple. He wasn't ready yet to return to Berk for good and he knew Astrid felt the same. And by all means, he wouldn't let anyone separate him from her ever again! That left only one solution, one very simple and very obvious solution.

Hiccup just needed to propose to Astrid.

. o O o .

Of course, this is not the end. But I write this in between writing 'What it means to be Chief', as kind of taking a break xD There will be 4, maybe 5 short chapters here, so more's coming soon ;)