Orlando | Rollins College alumnus Matt Rothschild grew up wealthy in a "deluxe apartment in the sky" on New York's tony Upper East Side. It sounds like a lush life, but Rothschild never met his biological father, and his mother dropped him off to live with his grandparents while she decided to travel the world rather than raise her baby. Rothschild—whose literary debut, the new memoir Dumbfounded (Crown/Random House, $23.95), details his life as a sexually confused, emotionally neglected Jewish kid surrounded by upper-crust, heterosexual Manhattan WASPs—brings pathos and humor to an exploration of a life in which he never quite fit in. But some might wonder how any Jewish person could feel isolated in the Big Apple, which has the largest population of Jews in the world outside of Israel.
     "Fifth Avenue is not Jewish, and that's where we grew up," Rothschild says, taking a bite of his roast beef on rye at Stonewall Bistro, which is just blocks away from his rental home in Orlando's economically depressed Parramore neighborhood. "When my grandparents moved to that building, it was the 1940s, and there was still a lot of discrimination. And I didn't even know I was Jewish until I was 7. Our isolation as Jews came from the fact that we were closet Jews. I think my grandparents—mainly my grandmother—didn't want anything to do with it because it [the Jewish religion and culture] was too much work. And my grandfather wanted to live in that building, and if living in that building meant conforming, that's what he was going to do." 
     Rothschild says that later, while studying comparative religion in college, he began to identify more with his faith and background. 
     "In college, I actually kept Kosher and went to a Chabad [an Orthodox Jewish student group]. Judaism was something I naturally gravitated to because it's the first religion where you can actually question things, where you can actually disagree. But I didn't have a core group of Jewish friends in Orlando—I certainly didn't have a core group of gay Jewish friends here. So then I started dating non-Jews and stopped keeping Kosher because I stopped believing that food is the dividing line between Jews and non-Jews," he explains.
     Early experiences being a closeted Jew also extended to Rothschild's burgeoning sexuality, which caused him to feel even more out of sync with his neighbors and classmates. Other boys his age weren't trying on their grandma's dresses.
     "I think my isolation came from a lot of things: not having conventional parents, knowing that something was up sexually but not being able to identify it, not really being able to be honest about things. For a long time, I didn't know the circumstances behind my mother giving me up," he recalls. "So I worried that my grandparents would also give me up—that stuck with me for a very long time."
     Rothschild recounts his first awkward sexual experience in the book. 
     "There's a chapter in the book called 'It's Nothing Personal,' which is about my first experience when I was away at boarding school, where I had a sexual relationship with my roommate, while he was sleeping," Rothschild shares. "He was not really sleeping. I mean, it turns out this is such a common story with people, where here I am thinking I'm taking advantage of this boy when in reality he's not sleeping at all. What happened [with my orientation] was that I knew something was off, but I was hoping that I was bisexual. Oh, please let me be bisexual, because then I could still marry a woman. And the first experience happened when I was 14. But it [my feelings for other men] hadn't gone away by the time I was 19, though. The sad thing is, the reason I chose [to attend] Rollins College was because of a girl. Yeah, I had a girlfriend. So we went to Rollins, and we were so in love."
     But wasn't the sex unsatisfying for someone who'd only fairly recently discovered his attraction to people of the same gender?
     "Oh, we never had sex," the 27-year-old admits. "I've never had sex with a woman. I didn't have sex in general until I was, like, 20. I was a late bloomer. Like, I was having oral sex [before then], but not intercourse. I think maybe I was more principled when I was younger. I don't know, I think I wanted to have sex with a woman, but somehow it just never happened or I chickened out. Ironically, though, I think as I get older, I'm becoming more attractive to women."
    According to Rothschild, writing a memoir can be wrenching process, even more so than writing a novel, because the writer must dredge up often-painful past issues to make the book genuine. 
     "The chapter called 'Driving Miss Sophie' was the hardest to write, because it's the chapter where my grandmother's illness [Alzheimer's] comes to the forefront, and I behaved in ways I've since come to regret," he says.
     Rothschild also notes that memoirists' works are scrutinized more than ever following the widely publicized fabrications discovered in the best-selling 2003 James Frey book A Million Little Pieces.
     "The book has become many different things over the last year and a half," he says. " It's difficult to look at the book as a single entity without thinking of the overall experience of writing it and the soul-searching and the questioning and wondering if I've done the right thing. Writing itself is just awful. I heard [lesbian author] Dorothy Allison (Bastard Out of Carolina) say once that when the words come and everything's working, it's better than sex, but the fact is, it's almost never like that. And I think it's silly when people get ruffled up about what's in a memoir. Any time you choose what to put into a book, you're automatically showing bias. And I'll be the first one to admit that I'm screwed up. And so, the stories are the stories, but when we talk about fudging chronology or creating composite characters... well, I lay it all out for you in the author's note—this is what I've done—and if you want to continue reading, fine. This is just one person's perception of events that happened 20 years ago. The fact of the matter is that it's also inaccurate because I don't see things the same way as I did then. And because I'm also a humorist, things are exaggerated for comedic effect. But the reader has the right to be frustrated if this is not explained ahead of time. And when you get caught," Rothschild adds, chuckling, "don't keep lying!"