In my exploratory draft I am trying to explore Wallace’s use of transvestism and homosexuality in the novel Infinite Jest. The character of Steeply, our US agent dressed as a woman, is one prime example. What does Wallace gain from making Steeply crossdress? How does that connect to the other examples in the novel, Poor Tony, U.S.S. Millicent Kent’s father? Wallace’s uses humor throughout the novel and my contention is that he is using transvestism as a source of comedy. I see the fact that *Spoiler Alert* most of the characters believe Steeply is actually a woman as the kind of low-brow humor we see in Mrs. Doubtfire and Big Momma’s House. He may be aiming for Shakespeare, but I clearly disagree. Then the representation of transvestism through Poor Tony and Millicent Kent’s father is even more damaging. Poor Tony’s situation only gets worse and worse. Wallace’s attempts to write homosexual characters seem to veer to the sterotypically butch (Ann Kittenplan, Millicent Kent) or to sexual violence. At times, the character and characterizations seem pointless. At one point a homosexual character is introduced, he flashes back to being violated by his father, and then the character is never mentioned again. Is the scene a sucker punch to the gut? An easy shock? That is the essence of what I am exploring. I am hoping to include other writing by Wallace. He examines sexual relationships and compulsions in a lot of his short stories. Also, to perhaps include other white heterosexual male writers of his generation. My hope would be his uses of sexuality are part of a trend amongst that select circle of writers. That would be ideal. Any suggestions/questions/directions?