@Techy Pony  
Which is odd. I thought up a possible ship with them the moment I saw a Cheerilee and Rick Astley pic. (I thought to myself ‘Stuff like this kind of happens often in Doctor Who.) So I’m thinking Cheerilee may have been a companion to the Doctor.
 
(I’m weird when it comes to headcanon.)

@Evowizard25  
She does seem similar to Cheerilee, but I’ve never seen that ship either xD

@Techy Pony
 
Cheerilee? They both are similar.

@Evowizard25  
Clara’s not too far fetched of a pairing, what pony is most like Clara… (Not Twilight)

@Techy Pony  
Actually I headcanoned that Colgate is the Doctor grandaughter. (You know, Susan of this world.)
 
The Time War wasn’t as bad, and some Time Lords survive to this day. (They were soldiers used by the alicorns to fight the Xenosian’s Chimera (Resistance style.))
 
And yes, I kind of shipped Twilight too (That makes the most sense, when dealing with FIM pairings), but then I decided Ditzy acted like Donna, so I made a relationship based on that. (And no, I don’t ship him with Donna. They’re just friends.)

@Evowizard25  
Martha and River are the only people I see as matching him at all. (If we’re talking ponies Derpy is a cute ship but not logical. Twilight and Colgate are the only ponies that I think match (I see Colgate as time pony not dentist, in which case Minuette might be the better name))

This isn’t going to end well.

@Techy Pony  
Martha was…of course the Doctor was still moping over Rose (Blimey, do I hate Rose Tyler).

@Evowizard25  
It’s not like his companions are usually relatable to the doctor anyway. But it is a weird shipping.

Ummmm…Is this some kind of new shipping? I’ve never seen it before and ‘whammo’ two pictures in one day by two different people.
 
(Not that it’s bad, but ‘eh Applejack and Doctor Whooves…don’t click in my head. Maybe that’s just me. Sometimes I need to read a good fic before I get into a pairing.)