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Twofers for both questions today! JUST BECAUSE.
Day 16 - What is the absolute worst pairing?

I don't hate on pairings very much, and I usually try to avoid making judgments like bad pairing instead of pairing I don't like. But if I'm going to pick a "worst pairing," it's going to be Laguna/Squall, which is somehow one of the more popular pairings in FFVIII fandom for no reason I can see.
I've complained about this one before, of course, but what it boils down to is a) Rinoa, b) Laguna is Squall's father and he knows it (and since Squall's not an idiot, probably so does he), and c) as of the end of the game Squall still just doesn't like Laguna very much - he respects the bond that Laguna has with Kiros and Ward, but that's about it.
Laguna trying to form a parental relationship with Squall would be interesting to me. Laguna and Squall in a romantic and/or sexual relationship just... isn't. I find it out of character for both parties and just generally completely unappealing to the point of "augh, stop that."
ALMOST AS BAD:

Another pairing that is inexplicably popular in fandom. This one's almost worse than Laguna/Squall in some respects, because Laguna and Squall at least have the potential to get along in some fashion. Luck and Dallas don't even have that. Prior to Dallas's rampage, Luck says up front that he thinks Dallas is a waste of space; after it, Luck fucking hates him and makes it quite clear that he is never going to stop hating him or forgive him for what he did. Basically the only way I can see Luck and Dallas managing to be in the same room as one another without Dallas ending up back on the bottom of the Hudson is if Eve mediates. There's just... no basis for a relationship there at all.
Day 17 - A pairing you thought would never work out, but did?

This is not to say that attempted murder is a dealbreaker for me or anything. But let me back up a little.
The screencap is from a ridiculous little visual novel called Yo-Jin-Bo, which is about how you-as-player-character, Sayori, get sent back in time into the body of a princess who's in danger of being assassinated, there to try to prevent this with the help of a whole team of hot bodyguards, few of whom have any concept of the sanctity of the fourth wall. (Only a few scenes in, one of the characters comes in for a lot of teasing about not being "one of the guys you can get at the end of the game". The whole thing runs like this.)
That charming gentleman up there is Ittosai, succinctly identified as the "glasses-wearing socipath" of the bunch, and while I cheerfully confess to liking the jerkass characters, Ittosai was a bit much even for me: he's pretty much only on board to kill things, and he's got exactly one sprite that's not of him making a crazy-face (and that one's an I'm-surrounded-by-idiots facepalm). Between that and the bondage wear (you can only kind of see it in this picture but what passes for his shirt is, yes, basically one long criss-crossing leather strap) I didn't figure Ittosai's ending would be worth much.
Then, of course, I actually did his route, and he started going out of his way to tell Sayori not to trust him and having backstory-laden nightmares, and around the time I hit the part of his good ending in which Sayori begs him to kill her and he says he will, and then he'll kill himself... yeah, I'm really predictable after all. It's pure "I can change him!" wish fulfillment, but I'm a sucker for it and it's played very well. His turned out to be my favorite endings in the game. Go figure.
But since that's really obscure and only involves approximately one and a half actual characters, have another one to go with it:

It's not that I didn't like Tamaki/Haruhi as a pairing when I started watching Ouran, mind you. It's just that the series is rife with subtext between just about everyone, to the point that I was pretty sure settling on specific pairings would be to the detriment of the series. My favorite Ouran pairings were basically Everyone/Haruhi and Everyone/Tamaki, after all, and while the series teased Tamaki/Haruhi a good bit, it also gleefully poked fun at Tamaki's assumption that the two of them would be the "official couple." I figured the series would end, like so many harem anime and manga series do, with none of the various love dodecahedrons resolved, and I was fine with that.
Then, of course, the series took its (somewhat) more serious bent, and as it turns out, I was wrong! Tamaki/Haruhi happened, and it worked very well, partly because they are genuinely adorable together and partly because the series didn't devalue any of the other characters' feelings or shuffle them out of the way by randomly pairing them up with other people we'd never seen before. So there you are.
Day 01 - What is your current favorite ship?
Day 02 - What was your very first ship?
Day 03 - A pairing that needs to happen now?
Day 04 - The pairing with the most chemistry?
Day 05 - The pairing with the least chemistry?
Day 06 - The best kiss?
Day 07 - The most heartbreaking scene?
Day 08 - The pairing with the most baggage?
Day 09 - The most believable relationship?
Day 10 - Why aren't these two married in real life?
Day 11 - What is your dream pairing?
Day 12 - Who had the best wedding?
Day 13 - What is your favorite television pairing?
Day 14 - What is your favorite book pairing?
Day 15 - What is your favorite real life pairing?
Day 16 - What is the absolute worst pairing?
Day 17 - A pairing you thought would never work out, but did?
Day 18 - What is the cutest pairing?
Day 19 - A pairing you've rooted for since the beginning?
Day 20 - The "can't stand the sexual tension anymore" pairing?
Day 21 - A pairing you like and no one else understands why?
Day 22 - A pairing you hate and no one else understands why?
Day 23 - A crazy love triangle/quadrilateral that worked out great?
Day 24 - A crazy love triangle/quadrilateral that worked out badly?
Day 25 - A pairing that was/would-be adorable, but could never work out?
Day 26 - A pairing that you hated and ended up loving?
Day 27 - A pairing that you loved and ended up hating?
Day 28 - A pairing that you will never understand?
Day 29 - What ship had the best proposal?
Day 30 - Your favorite ship forever and ever and ever?
Day 16 - What is the absolute worst pairing?

I don't hate on pairings very much, and I usually try to avoid making judgments like bad pairing instead of pairing I don't like. But if I'm going to pick a "worst pairing," it's going to be Laguna/Squall, which is somehow one of the more popular pairings in FFVIII fandom for no reason I can see.
I've complained about this one before, of course, but what it boils down to is a) Rinoa, b) Laguna is Squall's father and he knows it (and since Squall's not an idiot, probably so does he), and c) as of the end of the game Squall still just doesn't like Laguna very much - he respects the bond that Laguna has with Kiros and Ward, but that's about it.
Laguna trying to form a parental relationship with Squall would be interesting to me. Laguna and Squall in a romantic and/or sexual relationship just... isn't. I find it out of character for both parties and just generally completely unappealing to the point of "augh, stop that."
ALMOST AS BAD:

Another pairing that is inexplicably popular in fandom. This one's almost worse than Laguna/Squall in some respects, because Laguna and Squall at least have the potential to get along in some fashion. Luck and Dallas don't even have that. Prior to Dallas's rampage, Luck says up front that he thinks Dallas is a waste of space; after it, Luck fucking hates him and makes it quite clear that he is never going to stop hating him or forgive him for what he did. Basically the only way I can see Luck and Dallas managing to be in the same room as one another without Dallas ending up back on the bottom of the Hudson is if Eve mediates. There's just... no basis for a relationship there at all.
Day 17 - A pairing you thought would never work out, but did?

This is not to say that attempted murder is a dealbreaker for me or anything. But let me back up a little.
The screencap is from a ridiculous little visual novel called Yo-Jin-Bo, which is about how you-as-player-character, Sayori, get sent back in time into the body of a princess who's in danger of being assassinated, there to try to prevent this with the help of a whole team of hot bodyguards, few of whom have any concept of the sanctity of the fourth wall. (Only a few scenes in, one of the characters comes in for a lot of teasing about not being "one of the guys you can get at the end of the game". The whole thing runs like this.)
That charming gentleman up there is Ittosai, succinctly identified as the "glasses-wearing socipath" of the bunch, and while I cheerfully confess to liking the jerkass characters, Ittosai was a bit much even for me: he's pretty much only on board to kill things, and he's got exactly one sprite that's not of him making a crazy-face (and that one's an I'm-surrounded-by-idiots facepalm). Between that and the bondage wear (you can only kind of see it in this picture but what passes for his shirt is, yes, basically one long criss-crossing leather strap) I didn't figure Ittosai's ending would be worth much.
Then, of course, I actually did his route, and he started going out of his way to tell Sayori not to trust him and having backstory-laden nightmares, and around the time I hit the part of his good ending in which Sayori begs him to kill her and he says he will, and then he'll kill himself... yeah, I'm really predictable after all. It's pure "I can change him!" wish fulfillment, but I'm a sucker for it and it's played very well. His turned out to be my favorite endings in the game. Go figure.
But since that's really obscure and only involves approximately one and a half actual characters, have another one to go with it:

It's not that I didn't like Tamaki/Haruhi as a pairing when I started watching Ouran, mind you. It's just that the series is rife with subtext between just about everyone, to the point that I was pretty sure settling on specific pairings would be to the detriment of the series. My favorite Ouran pairings were basically Everyone/Haruhi and Everyone/Tamaki, after all, and while the series teased Tamaki/Haruhi a good bit, it also gleefully poked fun at Tamaki's assumption that the two of them would be the "official couple." I figured the series would end, like so many harem anime and manga series do, with none of the various love dodecahedrons resolved, and I was fine with that.
Then, of course, the series took its (somewhat) more serious bent, and as it turns out, I was wrong! Tamaki/Haruhi happened, and it worked very well, partly because they are genuinely adorable together and partly because the series didn't devalue any of the other characters' feelings or shuffle them out of the way by randomly pairing them up with other people we'd never seen before. So there you are.
Day 02 - What was your very first ship?
Day 03 - A pairing that needs to happen now?
Day 04 - The pairing with the most chemistry?
Day 05 - The pairing with the least chemistry?
Day 06 - The best kiss?
Day 07 - The most heartbreaking scene?
Day 08 - The pairing with the most baggage?
Day 09 - The most believable relationship?
Day 10 - Why aren't these two married in real life?
Day 11 - What is your dream pairing?
Day 12 - Who had the best wedding?
Day 13 - What is your favorite television pairing?
Day 14 - What is your favorite book pairing?
Day 15 - What is your favorite real life pairing?
Day 16 - What is the absolute worst pairing?
Day 17 - A pairing you thought would never work out, but did?
Day 18 - What is the cutest pairing?
Day 19 - A pairing you've rooted for since the beginning?
Day 20 - The "can't stand the sexual tension anymore" pairing?
Day 21 - A pairing you like and no one else understands why?
Day 22 - A pairing you hate and no one else understands why?
Day 23 - A crazy love triangle/quadrilateral that worked out great?
Day 24 - A crazy love triangle/quadrilateral that worked out badly?
Day 25 - A pairing that was/would-be adorable, but could never work out?
Day 26 - A pairing that you hated and ended up loving?
Day 27 - A pairing that you loved and ended up hating?
Day 28 - A pairing that you will never understand?
Day 29 - What ship had the best proposal?
Day 30 - Your favorite ship forever and ever and ever?