Lindsey has always had a thing for the bad girls (mostly Darla, and maybe Lilah as well) and the good now/who knows tomorrow boy (Angel). So what would be the attraction to Cordelia Chase, a good girl working for the other side?
Opposites do attract in this case. But there is a common ground, besides the fact that they are both very easy on the eyes. And that is the opportunity in front of them when it comes to goodness.
Cordelia left the Hellmouth for Los Angeles, looking forward to a career in show business. But the PTB seemed to have other plans. From Girl Friday to Seer, Cordy’s been on Angel’s side almost since the beginning. She could have turned her back on this life, pretending this world didn’t exist, but she decided to stick around and fight. Sometimes shallow (faking a vision_ lamely_ just so Angel would help superstar Rebecca Lowell) and business oriented (doing a night trip for owned money), Cordelia can’t deny her evolution. She’ll go to protect Gunn armed only with an axe and all the courage she can gather, something Sunnydale Cordy wouldn’t had done unless she was right behind the Scooby Gang. Even her dating standards changed because of Angel and Doyle. This girl is a bitka with a heart.
Lindsey grew up dirt poor in Oklahoma, seeing two of his siblings die and losing his home at the age of seven. He worked hard for what he has now. He was handpicked by Holland Manners while still a sophomore in Hastings. He’s the only Wolfram and Hart lawyer we’ve seen defending a guilty-as-sin client on court (Lee Mercer doesn’t count, since we only saw him sitting down in silence). He doesn’t seem to mind the kind of scourge he worked for (He was ready to arrange Cordy to be Russell Winters’ new ’companion’ before he even knew her). This changed when Vanessa Brewer’s latest work turned out to be murder children (Blind Date). His conscience kicked in, and the moment he decided to help Angel, he is given the choice to change his ways. He tosses it away for a promotion.
An important episode for both characters is the first season finale ‘To Shanshu in LA’. Cordy’s suffering at the hands of Vocah only makes her desire to help stronger, despite the pain that is sure to come her way. Lindsey’s confrontation with Angel, where the younger man reaffirms his staying with Wolfram and Hart, gets him his hand cut off.
In the end, Lindsey and Cordy are parallels, both faced with the option to do something good with their lives or walk away, they both take different roads. Cordelia can fascinate Lindsey, with her belief in good despite everything and vice versa. They can look at each other and see the decisions they discarded, how different their lives would be if only...
In a way, this two shades of gray complement each other..