Time to prove Monica is a two-faced skank.
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Don't gaze at it too long!
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Walkthrough
Go to the basketball court/park and meet Monica. She will be waiting on a bench. Talk to her, and she will be very friendly. The girls all come over and catch her hitting on you, which upsets her. They bring her boyfriend, Jake, who gets mad at you for hitting on his girl. He attacks you. He isn't part of the roleplay, so he doesn't have any crazy attacks. Defeat him and return to Annie with the news. Quest continues at Unplanned Parenthood.