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Once you get the Keystone from Dio at the Gold Saucer in Disc 1, you will be told that you can't go back on that day because the ropeway is out of order. Cait Sith will then suggest you spend the night at the Ghost Hotel, and, during the night, somebody will go to Cloud's room and "force" him to go on a date with them: that person can be either Aerith, Tifa, Yuffie or Barret, depending on your actions and decisions so far, turning this into a very subjective matter (Aerith being the most likely choice).

This involves all kinds of technical factors, like affections rates, that I would be no good at explaining; therefore, I suggest you check the Date Mechanics Guide at GameFAQs instead. Basically, though, what you must do if you want Tifa to be Cloud's date is have him be nice to her at all times and harsh on the other characters involved, especially Aerith. To be honest, due to Aerith being the most likely option and me being a CloAer supporter, I never got the date with Tifa myself, though I did look for information on what happens during it. The following is a short description of the events.

Tifa goes to Cloud's room and attempts to say something, but ends up claiming it's too embarrasing and, instead, she tells him she's willing to spend some time with him and that she won't take "no" for an answer. The couple leaves the hotel and heads to the Event Square, where the whole play scene unfolds: I don't find it relevant to describe it, since it will be the same no matter who you date. Once the play is over, they go to the Round Square and take a ride on the gondola (the climax of every date). Near the end of the ride, she finally gets the courage to tell him what she's been meaning to say: that it's hard being old friends, and that "timing is everything". Although she obviously means to say something more, she ultimately doesn't and the couple remains silent until the end of the ride. When they get off the gondola, Cloud finally asks her what she's been trying to say. She replies "nothing" and attempts at a change of subject, saying "it's getting too late".

Knowing Tifa, I don't think there's anything else we could have expected from her. Between Cloud and herself, always the shyness, always the time, always the past.

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