Several months later, after having back-alley reconstructive surgery to fix the damage Matt did, Cherry has a consultation at McNamara/Troy to have more reconstrutive work done, since the cheap one she got left her in such a state of disfigurement that she was fired from her bartending job for "scaring the customers away." She then demands the doctors do the surgery for free since Matt is Dr. Sean McNamara's son. Sean refuses however as he is angry Cherry attacked Matt and does not comply. Matt later approaches his dad and asks him to do Cherry's surgeries for free to clear his conscience. After the surgery, Matt goes to visit Cherry, the two become friends after a serious heart-to-heart. Cherry invites Matt to go shopping while they are in recovery, and while at the store, Cherry is insulted by the teller, which causes Matt to insult the woman by saying "she [Cherry] is more woman than you'll ever be." Here they run into Matt's ex-girlfriend Ariel. She threatens that she will spread word that he associates with a transsexual. Ariel furthermore is jealous asking Matt what Cherry has that she doesn't, then claiming that Matt must be homosexual as Cherry has a penis unlike Ariel.
Later, Cherry and Matt are both kidnapped by Ariel's father, Eugene. Eugene does not agree with the idea of a transsexual, nor the fact that his daughter's ex-boyfriend is associating with one. He tortures both Matt and Cherry by having them perform harmful and painful acts on themselves by holding them at gun point. Mr. Alderman then plays a sick game dressing Matt up in make-up and then deciding to cut the penis off whoever he thinks will be the "prettier girl." Matt is chosen but Cherry volunteers to have her penis cut off instead and then Mr. Alderman forces Matt to castrate Cherry. In a later scene, not shown how they got there, Matt is shown throwing dirt onto Cherry in a hole out in the woods. Eugene keeps telling Matt to "put the filthy tranny out of its misery". Matt stops and then begins to walk away and tells Eugene that he does not care if he kills him anymore. While Matt distracts Mr. Alderman, Cherry comes up behind him and hits him in the head with a shovel. Cherry picks up the gun then points it at the hurt Alderman. Matt tells her to "do it," and she shoots him (the gunshot occurring off-screen). Matt later states that Cherry only shot Mr. Alderman in the stomach, and that he is now in prison.