Spoilers: Massive, massive, massive to the end of AtS.
Angel and Lindsey belong together like Catholics and guilt. Really. Exactly like that. When I first started watching these series, Angel/Lindsey was the first slash pairing I ever noticed. Those two just seemed to bait each other more, to get angrier faster, to focus on each other so intently that, even in my newbieness, I had to figure there was something going on behind the scenes. They’re compelling together, they make me care about them. I hope they’ll get along, and when they don’t, I’m not surprised, because I understand how they work together, and I could anticipate them fighting. It’s a ship, a pairing, and the part of it that makes the most compelling argument for it, at least in my mind, is that I think of it as a pairing first, and a slash pairing second. There's barely any sly winking to the gayness of them. When the last word on Lindsey’s lips as he dies is "Angel", it isn’t funny.
Angel. Everyone knows that Angel has enormous guilt issues. Catholic, ex-mass murderer, Drusilla - choose your reason. All that guilt causes trauma (it would in anyone) and in Angel’s case, it results in a massive schism in his psyche much akin to multiple personalities. It’s not because of the soul – which I believe is what gives Buffyverse characters the ability to tell the difference between right and wrong, even if they don’t act on that knowledge. When Spike gets his soul, he never experiences a radical difference in personality. Souled or unsouled, Spike's just... SPIKE. Angel, however, wears Angelus like a pair of leather pants. The second that pesky soul slips away and the guilt is gone, he becomes Angelus. He can do all the nasty, nasty things he’s ever felt guilty for imagining – he actually has to. If he didn’t, if he had some restraint when he was soulless that wasn’t all about the evil, the division would be less clear, and he might have to admit that to think nasty things is as human as human gets, and that one needn’t feel so guilty about them to maintain one's humanity/soul/goodness. Angel, Lindsey and Darla are like different points on the guilt continuum here, which is why they’re all so interconnected in canon. It’s impossible to discuss this pairing without mentioning Darla, by the way, so I’ll mention her in this essay as well.
Darla tried to convince Angel to give up or ignore his soul many times. Forget about it. Do what the evil says to do and screw everything else. Especially guilt. This was Darla’s philosophy about how to deal with guilt – it’s not important. Ignore it. Guilt causes Angel a lot of pain so it's not surprising how he'd do almost anything to get rid of it. But with the soul-as-moral compass theory, Angel knows that ignoring his moral compass is wrong. He knows he needs to keep guilt around if he wants to be a good guy – guilt is what tells you you’ve done something wrong. Bad guys don’t feel guilt. So he’ll never succumb to Darla. She’s not a serious threat, even if she does offer some twisted version of love that might ease Angel’s painful and self-imposed loneliness. Angel won’t cave to her, because Angel’s problem is that he thinks that being a good guy means you have to keep all the guilt, that there’s nothing you can ignore. That puts a terrible strain on him that often results in brooding, but he won’t bend to ‘just ignore it, lover’.
What Angel needs is for someone to come at this from the other side. Someone who knows the difference between right and wrong, but ignores it in large part to do bad things. Not too bad, though. Whoever this is, they’ve got to still have enough caring in them to not do the terrible things – the things you don’t come back from – because between this person and Angel, they could solve a mutual problem. They could reach a middle ground. They could fix each other.
When Angel and Lindsey first meet in the very first episode of AtS, they’re supposed to be enemies. That’s the plan. Lindsey’s an evil lawyer protecting eviler clients, and Angel’s trying to kill the clients. Lindsey deals with Angel the way he’s been taught – smooth, slick lawyer who, along with his evil bosses and minions, rules LA. But Angel refuses to play by any of the rules – he interrupts board meetings and pushes perfectly orderly vampires out windows. He won’t talk to Lindsey, reads his card but doesn’t keep it, ignoring him just enough to insult him without speaking. Angel even pats Lindsey’s pocket as he puts the card back in it. Say what you like, lawyer-guy, but I’m doing what I want, and you can’t stop me. Nyah nyah nyah.
That first meeting is typical of them. Their interaction is always full of the unspoken – Lindsey threatening with a smile, Angel insulting without really looking like it. It’s childish and unnecessary, just like they both always are. They’re really alike in many ways – determined, even pigheaded. Childish when they’re angry or smug. They both brood. They’re both very artistic – Lindsey sings and Angel draws. Ultimately, they both have that dichotomy of the spirit – good vs. evil. When they’re together, they feel it more keenly because they’re so similar. They each like to pretend that the other is static and homogenous – Lindsey tries to see Angel as a guilt-ridden goody two shoes who isn’t capable of evil, and Angel tries to see Lindsey as a Black Hat he’d kill without a second thought, if only he didn’t have such useful information. The reason they get to each other so much, the reason they get under each other’s skin so well is that each of them knows that it’s not that simple. They know that a little bit of good/evil lurks in the other, and that makes them wary and afraid. And very, very attracted.
So, in season 1 of Angel, Angel keeps screwing up things that Lindsey’s working on until eventually Angel chops off Lindsey’s hand in the process of screwing things up. This is when the relationship turns around. In the next season, Lindsey screws up things that Angel’s working on. Angel has power now – W&H is focused on him, not the other way around. There’s much poking at each other (in a figurative sense, of course), there’s Lindsey trying to get something of Angel via Darla and failing and there’s Angel trying to get someone else to kill Lindsey for him, which definitely doesn’t work, because he too picks Darla. (She’s evil by now, and she knows it’ll cause more harm to leave Lindsey alive, to force Lindsey into contact with Angel, so she won’t get between them they way they keep trying to make her.) Finally, around the end of season 2, the boys team up to do the right thing. Lindsey’s gotta do something bad for W&H, and it’s so bad that even he won’t do it. But he can’t stop it alone, he needs help. Who does he go to? Angel.
Of course he goes to Angel. Lindsey’s trying to be good, and he knows that Angel’s the good half of him. He needs more than Angel’s fists to get through this one. But Angel doesn’t help him, at least not as much as Lindsey’d like. Angel won’t budge an inch from is idea of what good is. He won’t let Lindsey come to good in his own way, but insists that Lindsey conform to Angel’s rules. Well, Lindsey don’t play dat, sista. So, off he goes to find himself in his beat-up old truck – the one that Angel stole from him and broke – and we don’t see him for a long, long time.
When Lindsey comes back, he’s morally ambiguous. He’s played up as evil, but we all know better than to take that at face value. Turns out he’s really on the side of good, acting where Angel’s just reacting – going after the circle of the Black Thorn where Angel’s the complacent CEO of W&H – and he’s doing a better job of being the champion of humanity than Angel is. He’s unrepentantly good. He’s found his niche, he’s playing it to the nines, and he’s got the brass to pull it off. In fact, he seems like he’s totally without regret – he’s got the mission, and he’s full steam ahead.
But that's not good enough for Angel. You can't just have been an evil
vampire lawyer, and then give up your evil to be a good guy without any penance. That doesn't work; it's not the way we do things. If that's what happens, if Lindsey doesn't feel as guilty as Angel thinks he should over his past misdeeds but is still, to all appearances, trying to be a good guy, then clearly he'll be evil no matter what he does, even if he's trying to do good now. It'll come out sooner or later. That’s the way Angel has to understand the world, it’s the way the dichotomy has to function. So he has Lindsey killed. It’s one of the saddest moments I’ve ever seen – a white hat’s evolution cut short by one of the white hats.
The trouble is? Angel’s kinda right. We don’t know what he did in the two years he was gone, but it seems pretty clear that Lindsey’s very much the same man he used to be. He’ll use who he needs to get the job done, and he doesn’t care if they might not want to participate. Lindsey wants to be a good guy, but he doesn't get it yet that the ends don't always justify the means. He needs a lot of practice at being a good team player, because he’s not the best at consideration for his fellow man. What he needs most, though? Validation. For someone to see what he's doing right and to be acknowledged for that, that that's important. The backwoods Okie in him, who made the grade and cares about thread count now, still insists that he be like Lilah, only in it for himself... but he fights it. That's what makes Lindsey a character worthy of such compassion, and that's why I love him. It would be so easy for him to just give in to the power of the dark side, but he fights it. Even when he's so close. Even when Angel, his much-begrudged exemplar of Team Good, refuses to help him. He fights. That’s why he deserves help. And that’s why it’s such a tragedy that Angel has him killed.
If Angel and Lindsey had ever gotten together, they could have helped each other so much. Angel’s massive guilt issues and Lindsey’s sociopathy could have been exposed in their interaction with each other, and worked on once it’d been uncovered. Yes, it would have been angsty. Yes, it would have been painful and difficult and it would have hurt them both. But it would have helped them.
There are so many reasons to ship Angel/Lindsey – incredible chemistry, rich character history. They’re even funny together. But, at the end of the show, Angel and Lindsey are my OTP because they’re so absolutely, perfectly suited to one another.
And also, they’re really, really pretty.
http://www.atpobtvs.com/lmoram2.html#lm – Synopsis of the good/evil dichotomy in Lindsey