Chronologically

At first, from flipping quickly through the 'channels', it seems like the device is devoted to slightly different realities from Sam's senior year of high school. Then you realize that the seasons are changing, and the channels are in chronological order.

From the description on the device's menu, you know these are only realities where Sam experimented with men. It surprises you that there are channels for basically every day since Sam's 18th birthday. Your boyfriend is straight as the day is long (in your reality he actually never has experimented with cock). But, infinite means infinite.

As you stop at one where Sam's getting dressed, you decide that this is going to be fun.