Colin Singleton is a recent graduate from high school who has an infatuation with girls named Katherine. In fact, the day he graduated from high school, the 19th Katherine he dated broke up with him. The day after that, Colin took a bath. When he got out, he found his parents both in his room and immediately suspected the worst, wondering if one of his relatives had died. Actually, as his father said, Katherine had called his cell phone saying that she was worried about Colin. His parents were concerned about him, but Colin just wanted to be alone. They didn't leave him alone, but after he finally threw up in the bathroom, they got the message and left. In his bedroom, Colin decided to look through his yearbook, and came across Katherine's note. Colin read the word "forever," and felt sick once again.
That night, while Colin sat alone in his room, his Lebanese best friend, Hassan, burst in. Colin told him about what happened, and Hassan scolded him for being a sitzpinkler, German for "wimp." They argued until Hassan finally came upon the realization that there was a very simple solution to Colin's problem.
Hassan's idea was a road trip, but Colin's parents were not supportive of it at first. They didn't know the purpose, and felt Colin needed to do something that summer. Eventually, the two convinced Colin's parents to let them go, and all that needed to be done was for Hassan to convince his parents. At Hassan's house, Hassan's mother scolds Colin for "messing around with girls," boasting that she warned him about this. Colin told her that Hassan could teach him to be better on a road trip, but she didn't buy it. Hassan tried to convince her that he would try to "heal" Colin, and Colin lied that he would get Hassan a summer job in the process. This closed the deal for Hassan's father, and they let him go. The next day, Colin and Hassan woke up to drive south through Indianapolis. Colin drives, and once again thinks about Katherine, and his experiences with the 18 Katherines before Katherine 19. Each of them had dumped him.
As a toddler, Colin was always brilliant, and his parents considered him a prodigy. He began reading at two, and his parents quickly to a gifted preschool because of this. The school said Colin was too advanced and turned him away. He was sent to a psychologist who asked him questions and showed him words. Three years later, Colin was in 1st grade. He had no friends because they could not relate to him -- he was not like them. They thought he was weird and called him "Colon Cancer." This finally took a turn in 3rd grade, when he started dating 8-year-old Katherine 1.
The day after Colin and Hassan departed, they were in Kentucky. Everything still reminded Colin of Katherine, and Hassan was not impressed. Hassan, a Muslim, noticed a sign pointing to the World's Largest Crucifix, and excitedly forced Colin to start driving there, talking about how this road trip was about adventure. Colin reluctantly agreed, and they headed in the direction of the crucifix.
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