Season 5 episode 9

Madmax.

first, derpy hooves, then dr whooves, 2 and 2 together, add a W to derpys last name and bam, now your shipping like a mad cunt

I thought it was because they both had the last name (W)Hooves.

It definitely started before Hearts and Hooves Day, but I don’t know when.

At the beginning.

i got the inpeshion that derpy looks like Rose Tyler when peared with the doc

Standing with each other on the hearts and hooves day episode

Derpy is RoseTyler-blonde

@Vree  
That is mighty impressive. Good work.

@Vree  
Impressive detective work there.

Well the podcast and My Little Time Lord made it popular.

How did it not start is the question?

The stood next to eachother, and therefore are deeply in love, just like the origins of LyraxBonbon
 
Of course having fan names that match (Doctor WHOOVES and Derpy HOOVES) helped. as did the Doctor Whooves and assistant audiobooks.

Also, on @Grieffon’s comment, Hearts And Whooves Day came out in Febr 2012. It definitely WAS a good surprise, but I think the Doc x Derpy shipping fandom alread bloomed by the end of 2011. I can’t say shippers didn’t like the show “officially” confirming their ship (for what ponies standing next to each other is worth…) but it was more of a late bonus, it did not decide things.

Anyway, here is what I remember:
 
originally, he Doctor was paired with Twilight for a companion. This took of enough to birth a few pictures, some fanfics and the Doctor Whooves Advantures audio series.
 
Then we got Doctor Whooves And Assistant which as far as I remember was one of the first “big” things to associate th two characters with each other.
 
The some time in 2011 June we got some more shipping pictures, for example I’m pretty sure this was one of the first ones:  
http://turbojuk.deviantart.com/art/Stallion-and-Wife-212710851  
(if you go to the DocxDerpy DA group you can actually follow it quite well).
 
There were actually a few pieces of Derpy stalking the doctor before, but these were humorous and one-sided (with the Doctor being unwilling). It was during June-Dec 2011 that people started shippin them hard.
 
I think that it definitely helped that people wanted a stable father figure (even if surrogate) for Dinky too.
 
I may be giving too much credit to saturnspace, ’cause there are no traces of her activity (her tumblr starts with a mass upload in 2012 Jan), but I could swear that art like this one started a good half-year earlier. To me the reason she was so important was not just because she showed Doc # Derpy going the whole way being intimate (I think Dr Whooves was a more distant, outsider type, cameo character) but because she reconciled the Dinky x Sparkler crisis in the fandom after Sisterhooves Social by simply drawing them consistently alongside each other. Obviously it is bad to credit a single artist with this, there were actually a lot of people on in this at every step and I wish I could credit them all. But saturn may I think have made the most pictures on the topic.
 
And well, from then on it was pretty obvious development with Doc and Derpy being in the top 10 most popular BG ponies.
 
And of course new fans after that, like post mid-2012 just took the idea whole as they did the rest of our pony memes.

I blame saturnspace, her and “Doctor Whooves and assistant”.

Probably, the same way Vinyl Scratch x Octavia got started.

maybe?  
http://derpibooru.org/tags/artist-colon-saturnspace

@Psychopomf
 
@Grieffon
 
@EQUINE_excite
 
@Background Pony
 
@FancyCat2008
 
I belive it is a combanation of all these factors together, with some reasons more important than others for each individual.

@pokey274  
Three years? You mean the animators shipped them for some eight months before the show premiered? That’s gotta be an academy record!

I would have believed that they were both early fan named characters whose personalities worked well together. It has been almost three years since they were first shipped though so who knows for sure?

I think it was coincidental from Doctor Hooves and her being named Derpy Hooves

Hooves/Whooves are similar. Then it turns out the concept works quite well, and becomes popular.
 
Also, there’s this from Heart and Hooves day
 

I didn’t quite get it either, but after marathoning most of Doctor Who (still on the Tenth though), it may be because Derpy has long blonde hair like Rose.