broken kisses taste better when they're fixed

Okay, there are so many characteristics of their potential relationship to comment on, so I’ll just stick with the main ones. 

First of all, JK built Draco’s character to be so complex and intricately complicated that he, in my opinion, deserved a decent redemption. JK didn’t really give him that when she married him off to Greengrass, a pureblood who had never been mentioned previously. It kind of made all his character development pointless. 

Also, if you look in the books, there are so many similarities between both the Lily/James and the Lily/Snape dynamics with Dramione. You have the bullying aspect with James, and then the blood prejudice issue with Snape, and the parallels are so obvious. For example:

“…you’re just an arrogant, bullying toerag, Potter. Leave him alone.” -Lily Evans (OoTP) & “Don’t you dare call Hagrid pathetic- you foul- you evil…” -Hermione (PoA)

“She [Lily] had her own wand out now. James… eyed it warily.” (OoTP) ” & “Hermione pulled out her wand. Malfoy stepped backward.” (PoA)

And the Snape parallels are obvious: the whole blood status issue. There is no relationship in Harry’s generation that really represents a love that conquered all the odds and essentially saved someone’s soul, and Dramione would’ve provided the perfect opportunity for that. We know Draco was doubtful of the whole blood superiority complex anyway as he didn’t kill Dumbledore, but also because of his interactions with Myrtle. All he needed was a little pushing and caoxing, and Hermione would have been the perfect candidate.

Also, they are intellectually matched, and Hermione is someone whose intelligence is a key aspect of her character. No disrespect to Romione shippers or Ron, but he is not an academic, and if you look at relationships, academics tend to have more successful relationships with fellow academics. Doctors marry doctors etc. We know Draco is intelligent, and he and Hermione are both very fiery, passionate, ambitious, independent, and witty. The only thing that was really standing in the way was Draco’s past and what he’d been told to think, but his prejudices obviously started to crack towards the end of the series. 

If you search in the books, there are little hints dotted around (check Masha’s list), evidently not enough that it actually led anywhere, but enough to indicate that Dramione wasn’t impossible. The main issue, moreso than their characteristics, is the fact that the books are written from Harry’s POV. A Dramione relationship would require time and detail to make it believable to the readers, and the HP series is ultimately a fantasy/adventure/action series that was child-friendly, not an angsty romance series. Ron was the obvious and safe choice for Hermione, but with fanfics and fanart you can explore the potential for a Dramione relationship. Also, Pride and Prejudice. I mean come on. 

Also, check this from Senja! :D