If Red is paired with a game character, then the pairing is with game!Red. If he's paired with a manga character, then it's PokéSpe!Red. I was too lazy to differentiate every Red. Two completely different personalities, so I didn't want to confuse them.
RedShipping
Game!Red: …Hmm? Shippings? Maybe I'll give it a look at…
PokéSpe!Red: What's a Shipping? Romantic relationship? Oh boy…
AdultGameShipping – Red x Beauty (Trainer class)
…Um, no… I'm only eleven…
AffinityShipping – Red (game) x Pikachu
…Pikachu is a Pokémon…but he is my best friend besides Leaf and Green…
AntidoteShipping – Red x Emerald
Emerald? He's just a kid!
AscendancyShipping – Red (PokéSpe) x Giovanni
No, no, no, no, no, no… No.
BarrierShipping – Red (PokéSpe) x Lt. Surge
The Spoons of Destiny paired me with Lt. Surge. Not romantically. I don't think that's what they were used for.
BlackJackShipping – Red x Hilbert
…I've yet to meet him, but I've heard of him from N… He sounds like a strong opponent…
BloodDiamondShipping – Red x Diamond
Diamond makes the best food! I think he likes Pearl… Or Platinum… I can't tell.
BurningLeafShipping – Red x Leaf
…She's a very good friend… She tries very hard to get me to talk about my feelings… I think she told me she liked me one day just to see how I would react…
…She laughed about it telling me it was a joke, but I don't know…
ChampionHeartShipping – Red (game) x Cynthia
…She approached me one day on Mt. Silver and the first thing she said to me was why I choose to stand up here… When I didn't answer, she pulled out a Poké Ball and battled her…
…I lost… She was pretty interesting…
ChampionShipping – Red (PokéSpe) x Lance
Ahh, no! HE TRIED TO KILL US!
CheckerBoardShipping – Red x Black (PokéSpe)
Black's a good Trainer. He's very strategic. And also very loud…
ClassicAdvanceShipping – Red x May
…I met her on a trip to the Hoenn region… She challenged Champion Steven Stone of the Elite Four and lost… But I would like to challenge her one day…
ConclusionShipping – Red, Yellow x Misty
…? What?
CreepypastaShipping – Red (game), Pikachu x Ghost (Lavender Tower)
…
DepressionShipping – Red (PokéSpe) x Silver
Silver and I aren't very close. He really likes to keep to himself.
FirstTrainerShipping – Red x Kris
…She was upset with me when I wouldn't talk to her… I was waiting for her to challenge me, but she just kicked my shin instead… Then she challenged me… I don't know what that was about…
FreezeShipping – Red (PokéSpe) x Lorelei
…Don't even get me started on her…
GlitchyRedShipping – Red x Missingno.
…Guys… C'mon now…
GodTierShipping – Red (game) x N
…N flew to the top of Mt. Silver of his Zekrom and talked to me… He seemed to be a very lonely guy, so I decided to listen to him… I think he got upset after awhile because I wouldn't speak…
HeartGoldShipping – Red x Ethan
…This kid sure was rambunctious… He managed to defeat me once and wouldn't stop cheering for days… Until Kris kicked him…
HometownGalShipping – Red (PokéSpe) x Daisy Oak
I like to visit Daisy because she makes the best tea! And she's fun to talk to. I still can't understand how she's Green's sister…
HotPinkShipping – Red x White
White actually intimidates me a little. She's a nice girl, but I can't believe she's fourteen and in charge of her own agency. It's crazy what you can accomplish in life, I guess. I mean, I did become the Champion of the League when I was eleven…
I'mNotScaredShipping – Red x Brendan
…I haven't gotten much of a chance to get to know him, but I do know that he's good friends with May…
IsolationShipping – Red (game) x Silver
…I sometimes think this kid just needs a hug… I hope he doesn't get too close to Kris… She might kick him for not being responsive…
LifeguardShipping – Red (PokéSpe) x Poli (Poliwhirl)
Poli? Oh, no way! He's fun to hug, though. Squishy!
LivingLegendShipping – Red (game) x Red (PokéSpe)
Game!Red: …
PokéSpe!Red: …How would this work? What?
LuckyShipping – Red x Blue (female)
Blue? Oh, Arceus, no. She messes with me too much. Plus, she told me once that I wasn't her type…whatever that means.
MangaAdvanceShipping – Red x Sapphire
Too wild. I think Ruby would kill me.
MangaPearlShipping – Red x Platinum
Too distant. I think Diamond and Pearl would kill me.
MangaPokéShipping – Red (PokéSpe) x Misty
Misty and I are good friends, but she acts weird around me sometimes. I don't know what that's all about and when I try asking her about it, she avoids the subject. Hmm.
MountaintopShipping – Red (game) x Arceus
…God…?
NamelessShipping – Red (game) x Green (male)
…My rival and close friend, alongside Leaf… He's got a huge ego… Could I be in a relationship with someone like that…? I think the answer is no… I think he's still upset with me for demoting his position as Champion…
NoNewsIsGoodNewsShipping – Red (game) x Red's Mom
…My mother…? I am quite disturbed…
OriginalShipping – Red (PokéSpe) x Green (male)
Green! My greatest rival! And best friend, sure. But we're not romantically involved, haha. Could you imagine?
PoliShipping – Red x Gold
Gold's pretty cool. I like helping him train, but he can get pretty distracted sometimes. That's when Crystal started joining the training sessions, which only made it worse since Gold couldn't stop picking on her, to which Crystal would knock him out with a roundhouse kick… Yeah, I don't know when he'll learn…
PoltergeistShipping – Red (game), Silver x Kris
…Is this inferring that I'm a ghost…?
ProtagonistShipping – Red (PokéSpe) x Ash
It's kinda scary how much Ash and I look alike… We haven't gotten to talk too much. We're both always busy.
PsychoShipping – Red (PokéSpe) x Sabrina
Psycho is right… Uh-oh, did she hear me? Crap! RUN!
RattataShipping – Red (PokéSpe) x Bill
Bill's such a funny fellow. He's so hard to understand sometimes, though. I cain' seem ta make ou' wha' he's sayin' when he talks like this, y'know?
RedCapShipping – Red x Lucas
…I haven't met Lucas, but he's good friends with Dawn… She said she'd introduce me to him one day…
RedHueShipping – Red x Ruby
Ruby doesn't like battling. He believes in…beautifying his Pokémon… I don't know about all of that…
RedWineShipping – Red x Mei
…I have yet to meet Mei… I hear she's involved with some pretty heavy stuff in Isshu now…
ReformShipping – Red (game) x Giovanni
…Sigh… This has to be a joke…
RemakeShipping – Red (RGBY) x Red (FRLG) / Red (game) x himself
…What…?
ScarletJewelShipping – Red x Crystal
Crystal's a nice girl and a good friend. But…don't even make her mad. Gold hasn't seemed to learn that yet…
ShockShipping – Red (PokéSpe) x Pika (Pikachu)
Pika! Yes, Pika's my best friend, but just a friend. Why are you guys insistent on pairing me with a Pokémon?
SilentProtagonistShipping – Red x Dawn
…I've met Dawn a few times… She heard about me from Cynthia and was eager to meet me for some reason… She reminds me of Leaf… I don't mind talking to her…
SnapshotShipping – Red (PokéSpe) x Mewtwo
Mewtwo and I are good friends, just like I am with the rest of my Pokémon. Friends, guys.
SoulfulHeartShipping – Red x Lyra
…Lyra has battled me several times on Mt. Silver… She lost every time, but she returns every once in awhile to try again to defeat me… She sure is determined… I admire that…
SpecialShipping – Red x Yellow
Yellow? She's a really kind and sweet girl. Don't tell her I said this, but she has a really cute smile. She acts really skittish around me sometimes, though.
I wonder what that's about?
StaminaShipping – Red (game) x Ash
…Ash… I don't know who that is…
TotipotentShipping – Red (game) x Mew
…A level seven Mew randomly showed up on the Nugget Bridge one day… Imagine how shocked I was… It's a cute Pokémon, but I can't go out with it…
TownMapShipping – Red (game) x Daisy Oak
…Such a sweet girl… I'm not sure how she's related to Green…
UroborusShipping – Red x Hilda
…N has talked to me about her as well… I would like to challenge her as well…
Final Thoughts
Game!Red: …Not much to say…
PokéSpe!Red: …That was…interesting…I guess…
Whew! That was actually a challenge.
I know Red didn't seem too dense, but doing someone that's dense about what romance even is would just become too repetitive. Arceus, just wait until I have to do Ash's list… -_-;
~Midori
P.S. …Man, I sure made Kris/Crystal violent, didn't I?