At the start of Chapter 4 you’ll have to complete a motorcycle minigame segment. To earn Jessie’s affection - and this trophy - you’ll need to demonstrate your skill by clearing the segment without taking too much damage. At the bottom right of the screen you’ll see the life bar for your bike - as long as your life bar is roughly around the “N” in the word “Motonox Gust” (around 75% full) you’ll succeed. You cannot use retries to continue from checkpoints - you need to make the run all in one go. Fortunately with a little practice this isn’t too bad, just be sure to use your “Spinning Slash” attack ([Triangle]) whenever you can, watch out for the explosives thrown by Mobile Unit Officers and most importantly, play on Easy difficulty, and you’ll be fine.