From the artist's DA page:

And another addition to the "How They Met" series I'm working on. Turns out, I'm really enjoying making these! So far, this one has been my favorite.

Now to the story of this picture:

I envision Rarity's parents meeting when they're a tad older than most ponies would typically date and get married. Both of them are in their mid to late thirties (I use human years to judge magical pony ages… sue me) and have given up on love almost completely. Neither of them have had much luck with relationships, but their friends nevertheless encourage them to go to a speed dating night. After many dead ends with all of the other mares in the room, Hondo Flanks meets Cookie Crumbles. By this time, he's done with the small talk and jumps right in to what he wants: a loving marriage, a happy family, and in exchange for those he will be the best husband he could possibly be.

His straightforward bluntness, at first, catches Cookie Crumbles off guard, but his confidence and unblinking eye contact captures her heart almost immediately. He's not like the other stallions who sweet talk mares only to 'get lucky' and then move on to the next conquest. He seems mature, charming, gentlemanly, and every other quality she's looking for in a husband. Perhaps they've finally found their match…? Well, yeah, duh, obviously. They end up dating for the next eight months before Hondo kneels and proposes. The rest is history.

And as for the characters in the background: to the right are Trixie's parents and to the left are… um… well, Black Gryph0n's O.C. and… er… totally not mine. Totally not. Nope. (okay, fine, yeah, it's my O.C. Indy. Her design has changed recently to that of a Changeling, but that's exactly what I envision Black Gryph0n's reaction to meeting me would be: weirded out beyond belief :D)

I had lots of fun working with this one! Hope you guys like it!