Because it’s Intriguing - Fluttershy and Double Diamond. At first I thought the ship was crazy random, but now… I’m starting to get a good idea how this will go down. Double Diamond heads down to Ponyville for a visit to do skiing, and he runs into Fluttershy. She’s trying her best, but is slipping up. Double Diamond lends her a hoof with it and the two of them start having a great time. Later on, during the yearly Winter Wrap Up, Double Diamond tries to wake up some animals, but has about as much luck as Twilight during her first Winter Wrap Up. Fluttershy lends him a hoof, and he starts to at least understand that he had to be quiet and patient with animals. As the rest of the year goes by, these visits become more frequent to the point where they start to understand each other on a personal level and fall in love. Now Double Diamond resides down at Fluttershy’s cottage.
Because it’s Ship Teased - Party Favour and Night Glider. Image should say it all.
Because it’s Reasonable - Rainbow Dash and Soarin’. After more recent episodes, Rainbow Falls, Newbie Dash, Grannies Gone Wild, I’m starting to find the two understand each other very well. Rainbow Dash may like getting involved with hugs, but only when she chooses to, and doesn’t like it when ponies get into personal space. With Soarin’ however, she was completely comfortable with it.
Because they Protect One Another - Princess Celestia and Good!King Sombra. The Reflections arc should explain this sweet but tragic love story…
Because they Share Beliefs - Princess Luna and Thorax. Both of them want to get over their dark pasts and better themselves because of it.
Because of Subtext - Rockhoof and Mage Meadowbrook. There’s a lot of subtext in the comics apparently. Maybe Rockhoof was the colt Mage Meadowbrook met in the journal.
Because it’s Adorable - Sweetie Belle and Pipsqueak. Tell me, can anyone find a cuter combo than this one?!
Because it’s Realistic - Rarity and Fancy Pants. We all know Rarity hasn’t had a good streak of romances on the show. First with Blueblood being a jerk, then with Trenderhoof not being interested. As for Spike… well, I don’t think that’s getting anywhere. With Fancy Pants, however, he does seem a genuinely nice stallion, and Rarity did choose him as dance partner in A Canterlot Wedding. Maybe she’s got a new crush, who knows? As for Fleur… I don’t know. By the way she was acting around Fancy Pants, it seemed a bit off to me in Sweet and Elite. Maybe she’s toned down in other episodes, I don’t know. But I’m guessing they are close roommates or foalhood friends.
Because they’re Alike - Pinkie Pie and Cheese Sandwich. Super Duper Party Planner Ponies who love to sing and make others smile? Tell me what’s not alike about these two.
Because they’re Opposites - Gallus and Ocellus. Besides the obvious difference in species, Gallus is a bit abrasive and lazy sometimes but still athletic and loyal; while Ocellus is an openly nice girl, love studying and is kind to the core. After hearing Gallus’ backstory in The Hearth’s Warming Club, I knew he needed someone who would stick by his side. Who would be more perfect than Ocellus?
Because it’s Canon - Mr. and Mrs Cake. You can’t deny these two deeply love each other. Not only do they make that clear in many episodes (Mrs Cake freaked out when she heard that “The Cakes Are Breaking Up” in Ponyville Confidential), but they are great parents to Pound and Pumpkin and treat Pinkie Pie as if she was their own daughter.
Because it’s Non-Canon - Star Swirl and Mistmane. The more gentle Mistmane may be able to bring out a soft side in Star Swirl and the tougher Star Swirl may have helped Mistmane pursue her love for gardening.
Because it’s Charming - Twilight Sparkle and Flash Sentry. While they don’t get very far in canon, I do like the idea of these two ending up together later. That’s partly in thanks to Zack.
Because it’s So Crazy It Works - Terramar and Marble Pie. A kind seapony/hippogriff and a shy Pie sister? I made a full headcanon about this on the Seapony/Hippogriff Family Tree.
Because it’s Hilarious - Limestone Pie and Qubbie Pants. Again, full headcanon on the Pie Family Tree. I can just imagine all the conversations these two would have.
Because it’s Tranquil - Applejack and Caramel. It’s about as down to earth as the show gets. Two farmponies working the day away at Sweet Apple Acres.
Because it’s Full Of Emotion - Bright Mac and Pear Butter/Buttercup. Just watch The Perfect Pear. You will not regret it.
Because it’s Unique - Sandbar and Silverstream. A level-headed surfer dude pony with a hyperactive and bubbly hippogriff/seapony. Pretty cool and crazy idea, right?
Because it’s Cheesy in a Good Way - Big Mac and Sugar Belle. Hard To Say Anything and The Break Up Break Down will tell you why.
Because it Happened At The Right Time - Maud Pie and Mudbriar. When we meet Mudbrair, we’ve seen Maud enough times to know what she’s like and I feel she was ready to have a boyfriend. Mudbrair is perfect for her.
Because they Work Best When Together - Kettle Corn and Skeedaddle. Ah, how could I not interpret a foallike crush between these guys? Skeedaddle helped Kettle Corn get her cutie mark in haiku-writing, and he is blushing after realising what he helped her to do.
Because it Has Great Potential - Scootaloo and Rumble. I may have shipped them before Marks and Recreation, but now I ship them even more. I’m under the impression Scootaloo is a late bloomer and well eventually fly. And, I believe Rumble is a great candidate to help her. Through this, they will bond very strongly and perhaps they will get crushes.
Because it Makes The Series Better - Shining Armor and Cadence. Were shown to be a couple in their debut and are still going strong as of now. They are also great parents to little Flurry Heart and skilled rulers of the Crystal Empire. Shining is also Captain of the Royal Guard.
Because they have No One Else To Love - Flash Magnus and Somnambula. Well, this is also tied to the fact that I think their personas compliment each other well. Flash M. is brave to the core and can be stern sometimes (especially as a drill Sargent), while Somnambula is full of hope, calm and compassionate (tying into her job as motivational speaker).
Because of Fan-art or Fan-fiction. Zephyer Breeze and Sassy Saddles. I think I saw these two ponies paired together on a family tree somewhere, I can’t remember. But, I think it’s an intreasting combo. If they ever do end up together, Sassy Saddles can make outfits for the various ponies while Zephyer can style manes and tails.
Because Not Enough People Support It - Cheerliee and Breaburn. It’s a bit of an ‘out there’ pairing, but I think it works. Both are very cheerful and hard working, not to mention put the needs of other ponies first. I think the former is calmer than the latter though.
Because of Their Conversations - Tender Taps and Apple Bloom. Yeah, they are foals, but you can never go wrong with a foal crush. On Your Marks took me time to get sold on the idea, but now… I’m very happy they are in my headcanon.
Because it Brings Out (Or Could Bring Out) Their Best Qualities - Babs Seed and Featherweight. I get the notion there’s still issues about their pasts they need to resolve, and I think talking about it together could bring out their best qualities.
Because they Forgave Each Other - Starlight and Sunburst. I found it impossible to not ship them after The Crystallising (I quite liked the two parter to be honest). Sure, Sunburst left after he got his cutie mark and Starlight didn’t try to contact him, but after everything, they forgave each other. Starlight trusted Sunburst to do magic to help save the Crystal Empire, and Sunburst still trusted Starlight after she attempted to use a spell to relive her childhood with Sunburst. See what I mean?
Because I CAN! Queen Novo and Seaspray. I’m under the impression Skystar was out of a marriage with the Hippogriff king before his death from the Storm King. When in Seaquestria, Queen Novo married Seaspray out of political affairs, then they had twins Saline Blue and Haven Bay. These two aren’t in line for the throne as Queen Novo married into the Royal Family in the first place.