Many University of Chicago alumni have built their reputations with serious contributions in the form of Pulitzers, Nobels, and critically acclaimed publications. And others, like Tucker Max, have taken the low road. A graduate of the College in 1998, Max’s infamous website (tuckermax.com), where he recounts his sexual escapades with “several” women, is bookmarked on many a college student’s web browser. Offered a chance to regale his alma mater with bacchanalic accounts, Max did not pass up the opportunity for an Uncommon Interview.

CM: Why did you choose to attend the University of Chicago? What appealed to you about the U of C?

TM: It doesn’t really make a whole lot of sense now, but I was stupid when I was 17 or 18. My thought process was that I thought that I was legitimately a hyper-genius, and so I wanted to go to the hardest academic school I could to see if I was really as smart as I thought I was. I went to boarding school for most of my high school in New Jersey, so I didn’t understand how important social life was and how different it was in college. There was just so much that I didn’t get that I thought I did, but I was just wrong. So, that’s why I went to the U of C.

CM: Has your opinion of the U of C changed at all?

TM: I was actually down on campus a couple of weeks ago and I must say that the place has changed. There’s just a hundred little, itty-bitty, quality of life improvements that add up to make it a much more enjoyable place now. It was just very different when I was there. I mean, the student body is about a hundred times better looking now than it was when I was there. It was shockingly bad when I was there. When I got there, I was one of the best-looking guys on campus, and I’m not that good looking. I should never be one of the best-looking guys anywhere.

It was pretty funny: I dated my high school girlfriend all through undergrad and the only reason was because the girls at the U of C were so goddamned ugly. I couldn’t bring myself to dump her because, you know, she went to Vanderbilt and she was out-of-control hot. She was beautiful, but if you put her in a room full of stunning, beautiful women, she’s not necessarily going to stand out. She’s just going to be another beautiful girl. But when she came to visit me at the U of C, dudes would literally follow her around campus and they acted like they’d never seen a woman like this in their lives. You get so used to it down there that you forget what the real world is like. But, it is a lot better now than when I went there.

CM: Was there any redeeming feature about attending the University of Chicago?

TM: I loved class, I learned a lot, I met a lot of amazing people there, and in many ways, I’m a better person for going. But it was one of those weird things in that it was kind of like a love-hate thing. Because I definitely wasn’t getting any pussy and I wasn’t drinking, so I made it a point to, at least, take out of that school what it had to offer, which was a whole hell of a lot of intelligent people. I took the best professors there and I took every good class I could find. I would read the syllabus, the outside reading, and the bibliographies of the books that were on the syllabus because I had plenty of time. There was nothing else to do. I learned a lot.

CM: Reflecting on your undergraduate experience, what did you enjoy most? Least? Any notable defining moments during your experience here?

TM: Any notable defining moments? Let me see . . . So, I was taking an upper-level bio class and I was the only freshman in the class. One of my best friends, who was a sophomore, was taking the class with me and his name was Rand Funston. We were talking about viruses and disease vectors and stuff like that in the bio class. Well, this one girl raises her hand—I wasn’t really paying attention—and she goes, “Professor, did you read the op-ed in the Maroon today by Tucker Max? Because he says blah, blah, blah, this and that about AIDS.” No one in the class had any idea of who I was. People on campus knew my name from reading the piece because, you know, it’s a small school and everyone reads the Maroon. So, I was like, “What the fuck? Is this girl talking about me?” And then the whole class launches into, no shit, a 20- or 30-minute discussion that centered almost totally on my article. So, the whole class is going back and forth, blah blah blah, and I’m sitting there in shock. Then the same girl says something about my piece and it was wrong. So I interrupt her and I go, “I’m sorry. I really don’t think Tucker meant that. I think what he actually meant was this.” She turns around and gets this indignant look on her face and goes, “Ugh! That is not what Tucker Max meant at all!” [Laughs] Of course, the class is laughing and Rand goes, “You idiot! This is Tucker Max!”

So I guess the defining experience for me in my undergrad time was the column I wrote and all the weird things that spawned off from it. I mean, even with the two girls that I did get drunk enough to hit on or want to hook up with, 70 percent of the time they’d hate me and leave or throw the drink on me or whatever, whereas the other 30 percent of the time, that would seal the deal and they’d be like, “Oh, I totally want you.”

Oh. And just to answer the following question, which I know is going to be, “But didn’t you have a girlfriend?” Yes. I did have a girlfriend all through undergrad, and yes, I cheated on her repeatedly.

CM: How did your website come about?

TM: It started as a bet. My friend came across a date page where a girl asks guys to fill out an application to go out on a date with her. We were talking about it and she bet me that I wouldn’t make this kind of a page for myself. The whole thing escalated and, before I knew it, I put the page up in my second year of law school, and started putting up stories. My law school friends and I would go out and do stupid shit and get drunk and act like fools and we’d write up these funny stories about it. It was like ten of us in an e-mail group. So, I started posting those on the site and people just loved them. Everything just kind of took off from there. There’s really nothing and no one who writes like me and who writes about what I write about and in the way that I write about it, and there’s obviously a big market for it.

CM: Do you actively put yourself in situations that have the potential to make for good stories for your site, or do you honestly just naturally wind up in such situations?

TM: Honestly, it’s a combination of both. I have a certain personality type in that I basically have a 100 percent discount rate. If you’re not an econ major, what that means is that you don’t really care about the future very much and so you’re willing to take more risks.

CM: Do you think you will ever settle down for good?

TM: If by “settle down,” you mean being in a monogamous relationship with one woman and never cheating on her? That will never, ever, ever happen. I will never reach the point in my life where I’m going to be tired of having sex with lots of women and only want to have sex with one woman. I can’t even conceive of that. [Laughs] I definitely want kids and to have a family and a woman you love and care about, no question. But it’s going to have to be on my terms, at least in some regard.

CM: Well, what exactly are your terms?

TM: I will never in my life not have the woman I want. Assuming that she consents too, if I meet some girl I like and want to have sex with her, then I’m going to have sex with her. I can’t imagine ever putting myself in a situation where I’m not allowed to do that. I’m way too narcissistic to ever deny myself something I really want because of someone else.

CM: Are you willing to allow your wife, whoever she’s going to be, to have sex with other men?

TM: I’m going to have to cross that bridge when I get to it, but I honestly couldn’t imagine a fully open relationship. By the same token, though, you have to understand I’m honest with every girl I hook up with. Girls know exactly who I am. Even girls I meet out at a bar or wherever, if I don’t go home with them that night but they want to hang out again, I tell them, “Look, you need to go read my website.” Being deceptive in relationships and hooking up is just bullshit and stupid. All you do is hurt the other person and end up losing part of your soul. Women go out, just like guys, with agendas, and they have all different types of agendas. You can usually tell what the girl is looking for, and if she’s looking for a relationship or that sort of thing, then I’m the wrong dude. If you’re looking for someone to hang out with, hook up with, drink, and have fun with, then I’m great. It just depends what you want.

CM: Who were the prettiest, smartest, dumbest, and/or ugliest girls you’ve ever slept with?

TM: [Laughs] I don’t even know how to answer this question. Prettiest? I don’t know. Literally, spread from the hottest to the ugliest girl I’ve hooked up with pretty much encompasses a huge range. I mean, the bottom of my list could be like Ripley’s Believe It or Not and the top are literally world-famous models who are world-famous for their beauty. The only way I could describe this any more is to give names and either you wouldn’t believe the names, or I promised I wouldn’t say.

I’ve never hooked up with any of my professors. Actually, I hooked up with a female grad student once, but I was ten times smarter than she was. She was a T.A. for one of my U of C classes. I’ve hooked up with a lot of smart girls. For Christ’s sake, I went to the U of C! I hooked up with two girls who were Rhodes Scholars when I was there!

As a group, I’ll tell you, the dumbest women I hooked up with were in Florida. I lived in Florida for a year after law school because my father has a business down there, and it was just shocking. I literally felt like after living there for a couple months that I had become stupider. It was unbelievable. If you read the stories on my site that are based around crazy women, about 75 percent of those women were in Florida…and I only lived there for a year.