Star Trek: 10 Biggest Mysteries About Guinan
7. When Did Picard First Meet Guinan?
The episodes Time's Arrow parts 1 & 2 depict Guinan's first meeting with Jean-Luc Picard. This had been teased for years, not least by Gene Roddenberry himself. When Whoopi Goldberg began appearing on the show, he said that their relationship was far deeper and far more meaningful than anyone in the audience had ever suspected.
Guinan herself echoed these words in the Best Of Both Worlds part 2, after Picard's assimilation. She explains to Riker that Picard meant more to her than friendship, more than family - and she was willing to let him go, understanding the Borg as she did.
Star Trek: Stargazer Oblivion depicts their first meeting from the other way around. In fact, this is the first time that Picard meets Guinan, whereas she already knows him. She doesn't let on, however, that she has prior knowledge of her old friend. In fact, it isn't until Time's Arrow part 1 that she even reveals this. She asks him 'do you remember when we first met?'
He replies 'of course'. She counters with 'don't be so sure.'
This mysterious relationship is one that spans hundreds of years, while also covering mere decades.