This comes out of a discussion on Sketcha-Holic's story Brother Bothers, which she just finished (and which you should read). A few of us got talking about how old Pinkie and Cheese are, and how old they are relative to each other, and I thought it made sense to have that conversation here instead of monopolizing her story thread!

I think it's pretty clear that they can't be that far apart in age, since he's a colt when he sees her as a filly. There's lots of wiggle room here. My Equestria Girls Cheese is a class ahead of Pinkie, and he's about ten months and ten days older (her birthday is early May and his is mid-June.) As for regular Pinkie and Cheese:

Well, he looks younger than she is in the flashback, although it's hard to tell. He's definitely shorter, and of course he's a blank flank, but that doesn't mean he's younger, since boys mature later than girls. Purely my headcanon: he's a late bloomer, which didn't help with being teased and feeling out of place at school. One cutie mark and a major growth spurt which resulted in a tall and skinny Cheese and a lowered voice and getting rid of the glasses, and it's not surprising that Pinkie didn't recognize him.

I think Cheese tries to act older than he really is. The artificially lower voice and calling the Mane Six "little fillies" is part of that. That, plus in his head she is this sweet, innocent, cute little thing who has been pretty much unspoiled by life (true), and that therefore she must be shaded from some of the tough things that he, Cheese, has experienced, which is hilarious when you consider that Pinkie has faced off against Discord, Nightmare Moon, a dragon, Chrysalis, and who knows what else. It's both chivalrous and adorkable, I think, because he is every bit as naive and sweet as she is. Pinkie is as sweet and unspoiled as she is not because nothing has ever happened to her, but because nothing has ever made a dent that she couldn't erase with laughter and some cupcakes. For a specialist in weaponized laughter, Cheese is a bit dense about this. Silly Cheesie.

So that's my headcanon. What's yours?

3805801 I have nothing to say except:

It actually explains a lot about him, especially why he doesn't just settle down after he runs into Pinkie Pie and tells her who he is.

3805801 Hmmm. Those are some good points! It makes sense that Cheese would act older than he is so he could be more respected, especially by Pinkie.

My headcannon is a little darker than yours, but similar. I suppose I view Cheese as a little older than Pinkie, but acts like he's a lot older. In my mind, he acts that way because he had to grow up fast on the road. From an early age, he had to convince ponies that he was responsible enough to live on his own and earn a living for himself. He worked so hard for respect that he has trouble admitting that he is young and inexperienced in a lot of areas. As a teenager, he was always touchy about being called a kid, so he overcompensates with his cool persona. And then Pinkie comes along and sees right through it. That's how I see him anyway.

3805801
3805968
I love both of these headcanon accepted.

Transposing my estimates from the other thread...
========================================

I have Maud be five years older than Pinkie, which if we have Cheese be one year older than Pinkie makes Maud seven years older than Tommy. My ages for the characters at the end of Season Four (YOH 1504) would be Maud 28, Applejack 26, Fluttershy and Cheese Sandwich 24, Pinkie Pie 23, Rarity and Rainbow Dash 22, Twilight Sparkle 21, and Tommy 20.. Which puts them all in the "twenty-something" group. Both in our culture and Equestria, twenty-somethings don't see age differences between each other as mattering all that much anymore.

Age issues were once important between Cheerilee and Big Mac, who are 32 and 30, respectively, at the end of Season Four. That's only a two-year age gap, which is irrelevant to them now but made a big difference to them when they were teenagers and the 13-year-old Mac was attracted to the 15-year-old Cheerilee, who in addition was spending most of her time at high school living in Canterlot at the time, so Mac was in addition to being a "child" compared to her also a "country bumpkin." That's why their Toy Ship didn't get promoted to adult status until much, much later.

Age issues were almost completely unimportant between Piercing Gaze, who was 41 when he met the 19-year-old Trixie Lulamoon in 1499. They were completely washed out by the other and more severe issues, such as Piercing's Madonna-Whore Complex and Trixie's utter terror of her own sexuality, with a side order of arrogance for both of them. They're now 46 and 24, respectively, and have worked their love out a bit more happily, though Trixie is still obsessed with proving herself to him and to the whole world.

They were more important between Humanoid Piercing Gaze and Trixie, but then those two met when he was 36 and she was 14, which made her an actual "child." Through a strange resonance between the two worldlines, the outcome was similar, and happened when they were both at the same ages, 41 and 19, though the emotional effects on them were very different since they'd known one another five years instead of just under a month, and consequently had much stronger bonds.

This is a "strange" resonance, like the existence of those two and many more personality analogues to begin with, because the Point Of Departure between those two worlds came when Humans died out in the Eldren Apocalpyse 110 thousand years ago on the Pony Earth, and the Ponies died out in the same event 110 thousand years ago on the Humanoid one. By merely quantum-mechanical interpretations of Many-Worlds, the two worldlines should not be even remotely similar, yet they contain almost identical individuals -- despite the fact that their dominant sapients come from two different mammalian families!

... and that therefore she must be shaded from some of the tough things that he, Cheese, has experienced, which is hilarious when you consider that Pinkie has faced off against Discord, Nightmare Moon, a dragon, Chrysalis, and who knows what else.

Oh yes. Under the sweetness and cuddliness, Pinkie Pie is as tough as the rocks of the White Tail Mountains. She wouldn't be alive and sane if she weren't.

I think that they could be an age or two apart. Cheese is a bit more mature in nature, plus he's a boy, so he's taller and a bit lanky (But that's just how he's made) And Pinkie doesn't really act her age sometimes, but yeah

3805968

Cheese Sandwich encounters dangerous situations more often than Pinkie, because he's on the road while she's sedentary. However, the dangers he faces are mundane ones -- storms, bandits and predators -- and he's rarely the target of focused or overwhelming violence. Pinkie, on the other hand, has fought giant monsters, meta-equine sorcerors, and mad gods -- and even survived some hits from them. And her Reality Warping is stronger than his.

3806268

and he's rarely the target of focused or overwhelming violence

Let's just say in my headcannon he was the target of focused violence for years before he left Manehattan.

Anywho, that's a good point about Pinkie fighting the monsters. I forgot about all the magic stuff with Pinkie mostly because I tone down the magic a LOT when I write so I can focus on the slice of life elements. The one big downside to my universe if I'm being honest.

My take is that in the ManeVerse, CheeseSandwich and Miss Pinkamena Diane Pie are nearly the same age. The EGVerse simply does not make sense:

The EGVerse seems to be a distorted version of the ManeVerse. I twould not be surprise me to discover that everyhuman with a counterpart in Ponyville spends their live in CanterLotHigh because it seems right to them. In the crazy EGVerse, all of the inhabitants of Pnyville are trapped in the HighSchoolLoop.

The age-difference between Miss Pinkamena Diane Pie and CheeseSandwich does not matter in the EGVerse because they are eternal teenagers.

3806506 Yeah. EG just complicates the whole age thing by throwing Big Macintosh and the CMC into the high school. It completely disregards all logic, unless Canterlot High is somehow big enough to include every single class from kindergarten to college which is not likely.

3806554

The CMC in the EQVerse are 14. Big Mac's not a student, he's a graduate of CHS. Note that he's dating Cheerilee.

3806554 Well, of course, it's just for convenience--but having the CMC there isn't that crazy if you imagine it as a junior-senior high school. It just means grades 6 or 7 through 8 are housed on the same campus, and that's not all that uncommon. That would put the CMC at about 11 or 12--a little older than I think of them, but not much.
3806506 Actually, when you're writing it, their age matters a lot more in the EG verse. The movie gets away with it, because they only show the social parts of high school, but I got caught up in exams and athletic calendars and weekdays vs. the weekends and graduation and who knows what. In fact, if you trace through LGW, there's a consistent calendar with certain events happening on certain days, including the Little League games. I made it easy on myself by using the 2014 calendar, but I messed up with June. The important bit is that the Cake Festival happens on the first Saturday after graduation, and also happens to fall on Cheese's birthday.

I don't know why I have such an obsession with calendars. It's so bad that in my unpublished Victorian Gothic, I picked a specific year and made sure everything lined up with the ecclesiastical calendar and grouse season, among other things. Nobody will notice, I told myself, but I knew I would.

So that's why I had to have a specific age with a specific birthday (that, and there was a plot-related reason for doing so.) In Equestria, it's probably enough to say, "eh, they're almost the same age." I'm only going to raise an eyebrow if someone insists that Cheese is a LOT older and more experienced than she is.

3806578

You noticed the EasterEgg in Shake Your Tail. It also has things like Miss Pinkamena Diane Pie riding herself, Discord, et cetera.. Given that the short Shake Your Tail is the fantasy of Princess Twilight Sparkle, I do not know whether we can believe it.

In the movie, during Shake Your Tail, the HuMane Miss Rarity becomes a Flashy Puppet. This is funny because she is a FlashPuppet.

3805901 That is a pretty awesome picture, btw. I like TexasUberAlles, but I hadn't seen that one.

3805801
I... don't have a headcanon for Cheese. Oh, sure, the idea I used in Cheese Pie Cake was pretty original, but it's just that: an idea. I didn't accept it as a personal headcanon, because, really... I thought it was kinda bland. I didn't exactly delve too far into it, but I did like the idea of Cheese and Pinkie sharing the same birthday, if only for the fic. And as you might know, Cheese was the same age as Pinkie in Cheese Pie Cake (21, if I recall), and I thought it was pretty cool. I know it kind of contradicts your own headcanon about party ponies not remembering their own birthdays and all...

But, that's the thing: I've found that yours and Sketcha-Holic's headcanons are pretty damn amazing. Yours with the magic and party ponies and all, and Sketcha's what with Tommy. So, really, I've just kind of absorbed both of yours as headcanon. I just prefer to keep Cheese Pie Cake as using an idea rather than headcanon. Because you've got a good idea going about Cheese pretending to be older than what he could be. Given he's a bit lanky as well, and his voice sounds a little like an older pony, I'd say it's likely possible that he's a few years ahead.