On Tango in the Night, Lindsey and Christine worked together a lot - Mystified, You and I Part II, and this catchy little number. While Lindsey didn't write the lyrics here, I'm sure he could have related to this song about wanting something and knowing it's not going to happen.
When Christine McVie was making her solo album in 1984, she spent a large amount of time in Switzerland. At one point, in either the fall or winter, she called Lindsey to visit her at her hotel on Lake Geneva. He went for a week. He ended up playing on her solo album a little, but he was initially just called to spend time with her.
There has been, elsewhere, discussion of a romantic relationship between Christine and Lindsey and I think that this is what was happening at that time. There's an obvious attraction (anyone who has seen the video from 'Mirage' has seen Christine checking Lindsey out during 'I'm So Afraid' when he's on that side of the stage... she happens to glance over a number of times. Also, they talk or laugh together a lot, i.e., during 'Sisters of the Moon' and he often crosses the stage to her) and Lindsey has spoken of his feeling as if he had known her before they even met, having a connection like that.
But, at the same time, Stevie and Lindsey still had some sort of a relationship. As they have both admitted, their relationship didn't really end until their fight in 1987 when Lindsey left the band. Maybe, at one point, they even became friendlier again (perhaps after the Mick/Stevie/Sara thing), maybe he was sympathetic to her loss (all prior to 1987, though).
Now, the song's connection. I, obviously, think that this song is about Christine and Lindsey's relationship (having Eddy, Christine's now ex-husband, working on this song is interesting if that's the case...hmm...). I also think that this song is about the people left behind... Stevie and John. Really, how would that have been for Stevie? Her best friend (Robin's gone, as is Sara, which leaves Christine as probably her closest confidante) gets with her man (well, one of her men) - reminiscent of Sara and Mick from the beginning of the decade.
I should mention here that I don't think, assuming that Christine and Lindsey did have an affair (that will continue henceforth), it meant as much to her as it did him. I'm not sure one (Christine) ever quite reached the same level of affection for the other. He seems, now, to have cared more... with her, I think it may have been something but not the something Lindsey may have made it out to be (even more recently, she says that they're just friends where he was still talking about deep connections and such).
So, the song.
"So cool, calm and collected
You had a style, a rakish style
Well my poor heart
You'd stay so long on my mind"
If you think of Lindsey as a person (ignore the role he plays onstage or in the studio), he seems like a generally mellow person (as in 'The Making of Rumours'), connecting to the "cool, calm, and collected" line...and he certainly does have a style which could be described as 'rakish' (dashingly or carelessly unconventional, as defined). And as I mentioned before, I think he put more into the relationship than she did...whatever level it actually got to is still up for speculation. "You'd stay so long on my mind" - With an affair, it would not be easy to forget the other. The drama that most likely ensued from the revelation of this relationship to the rest of the band would have made it so one could not have easily forgotten the other. I'm sure, too, that their affair would have been significant enough to stand for itself.
"Well isn't it midnight
On the other side of the world
Do you remember
The face of a pretty girl
The face of a pretty girl"
I think that Christine would have been more likely than Lindsey to think about the people a relationship between them would affect (i.e., Stevie and John). So, I think in the chorus, the "pretty girl" could be Stevie and, with the assumption that Lindsey and Stevie still haven't found closure with their own relationship, Christine might wonder how Stevie would be affected. Also, if they were together in Switzerland, Stevie and John would be halfway across the globe, geographically. In short: if Lindsey tried to start something between him and Christine (I see him as the aggressive one in the relationship), she probably wondered how things were between him and Stevie. Were they together? Were they not? Was he over her? Did he remember, if he wasn't over her (Stevie), that she (Stevie) was still there... ¦maybe far away, but still there, probably anticipating (to some degree) his return (especially if there was still something going on between him and Stevie).
"Looking back so long ago
You had a knack, a knack of
Making women know
Ooh there wasn't the time
And I knew you'd never be mine"
I see this last verse like this:
The first lines are hard for me to interpret. What did he have a knack of making woman know? Perhaps, he made sure that people knew he was no longer with Stevie, but now things were all messed up again (see above) - were he and Stevie together or not? Did he even know? So, then the next lines ("Ooh, there wasn't the time/ And I knew you'd never be mine") could be thought of in two, somewhat similar, ways. Either Christine felt that he would always be in love with Stevie thus they could never REALLY be together, he would never really belong to her -OR-- because of the circumstances of their meeting and their working together, she may have felt that perhaps in a different time or different place, if they had been different people they could have had something substantial but she didn't want to get involved with another member of Fleetwood Mac and have a deep relationship...
Final note: I think that maybe 'Isn't It Midnight', 'When I See You Again', and 'You and I, Part II' may all be interconnected, relating to the presumed relationship between Christine and Lindsey.
Just a thought...
I've heard that the song is about Dennis Wilson, much as the song "Hold Me" supposedly is.