Sawyer describes it as 'a way of getting to know each other.' A player says 'I never' and then finishes the sentence with a statement about themselves. If any of the other players did do the described action then they must drink. However, this also includes the questioner, so one must weigh up whether to ask a very insightful and personal question against the fact that they might also have to drink. Of course, one could always lie. Players switch the role of questioner between them, usually going clockwise around a group.
Sawyer first points out that Kate must never have gone to college, considering that she's never heard of the game.
He then gives the example to Kate that he's never kissed a man, while she has.
Kate retorts to the college question that "I never implied I went to college." Sawyer drinks.
Sawyer says he's never been to Disneyland. Kate does not drink.
Kate says she's never worn pink. Sawyer drinks, saying "the 80s."
Sawyer says he's never voted Democrat. Kate doesn't drink, replying with "I never voted", rightly guessing that this will make Sawyer drink.
Sawyer says he's never been in love. Kate drinks.
Kate says she's never had a one-night stand. As the subtext puts it "Sawyer takes a healthy swig" and asks whether he should drink for each one.
Sawyer says he's never been married. Kate takes a sip, saying it didn't last very long.
Kate says she never blamed a boar for all her problems. Sawyer drinks, and seems angry.
Sawyer replies that he never sought 'carte blanche' [blank cheque] just to spend time with the only other person who doesn't belong. Kate drinks, also now angry.
Kate quickly fires back that she never carried a letter round for twenty years because she cannot overcome her emotional baggage. Sawyer drinks.
He then says he never killed a man. Kate drinks, looks upset, then so does Sawyer.
Neither Sawyer nor Kate went to college.
Sawyer's assured attitude that Kate has kissed a man is suggested by the subtext to darkly refer to their kiss. ("Confidence Man")
Neither have ever gone to Disneyland, though its interesting that Sawyer says its 'plain sad' that Kate hasn't, yet he doesn't drink himself, suggesting he too has never been.
Sawyer wore pink during his teenage years, as was fashionable in the Mid 1980s.
Sawyer has voted, but never for a Democrat, perhaps reflecting his Tennessean background where there is a very strong Republican majority. Meanwhile, Kate has never voted.
Kate reveals that she's been in love, and is probably referring to either Tom Brennan, her childhood sweetheart, and/or Kevin Callis, her ex-husband. In contrast, Sawyer says he has never been in love, though the subtext here says Kate does not believe him. However, we later learn that Sawyer did get very close to a woman named Cassidy, and told her he loved her, though this could have been part of the con. ("The Long Con") ("Born to Run") ("I Do")
Kate has never had a one-night stand, while Sawyer's actions demonstrate he's had many.*
While Sawyer has never been married, Kate has. This is undoubtedly Kevin Callis, the man who Kate was briefly wife to. ("I Do")
Kate's reference to a boar referred to the current episode context as the two were at the time on a mission to find a boar. Sawyer's reply of 'carte blanche' also referred to Kate's demand for helping Sawyer in the episode, but the question also suggested that Kate values the relationship she has with Sawyer as he is one of the only people who seem to understand her ("Tabula Rasa") ("Outlaws")
Kate's statement about a twenty year-old letter refers to Sawyer's letter to the real Mr. Sawyer who caused his father to kill his mother and then himself. ("Confidence Man") ("The Brig")
Finally, both Kate and Sawyer reveal they've killed in the past. Sawyer is probably referring to killing a man he believed to be the real Mr. Sawyer (later revealed in flashbacks of the same episode), while Kate is probably thinking about her father. However, this is assuming that the two have not killed more than one person. Kate herself believes she was responsible for the death of Tom Brennan, whom she refers to as "the man I killed," even though his death is later shown to have been from a car crash and police gunfire. ("Born to Run") ("Outlaws") ("What Kate Did")