Soon after your shopping trip it's time to meet the next client. You meet Jesse beforehand.
Jesse: "I can't believe you have an actual gun! Hopefully it will be useless..."
You instruct him to keep it in his purse. He's the one that drives the client after all. He's reluctant since it's a crime to have it, but agrees it's for his own safety.
Jesse: "I suppose you'll be making me into a girl again? (Haha)"
Correct. He makes a far better ambassador as a cute girl! You swap her, then head off to the beach cave.

...