The actual easiest way to get the "challenge" achievements

Discovered by accident through impatience. Faster than the other method of "T to solve then pray for RNG". This is solely for the "(Girl's name) challenge" achievements that want you to win twice in a row or lose many times to gain the achievement.

The strategy

Step 1: Start the puzzle you need the achievement for
Step 2: Immediately press "T" on your keyboard
Step 3: Choose Rock, Paper, or Scissors
Step 4: Right after making your choice, immediately spam you spacebar a handful of times. 5-6 should do. A bunch of text showing "Draw" "Win!" and "Lose" should pop up as if you made many selections very quickly
Step 5*: Wait a second for the girl to undress
Step 6: Profit

* Note that sometimes the game will freeze and nothing happens after this step. If so, click the back button on the top left and repeat steps 1-5

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xanks keng/quen (read this like heavy tf2)