"It's all shrouded in protective language."

Age 24, London.
Fledgling film producer

Winnie Li '00
Photograph by Stu Rosner

How do you meet people? "I don't date, at least in the conventional sense. Dating seems like a mechanical, weird, dehumanizing process. People meet in bars and exchange business cards—and based on that decide if they want to go on a rotating cycle of drinks, dinners, movies, et cetera, with each other. It seems tiring and superficial. Nobody says anything deliberate like, 'Do you want to go on a date with me?' But either he or I might say, 'Do you want to hang out sometime?' It's all shrouded in protective language.

"A lot of my friends tend to be guys, which can create awkward situations sometimes—they think there's something brewing between you, or you think that, but everyone's too scared to mention it for fear of disrupting the friendship. I've hung out with guys before, and then at the end realized, 'Wait, was that supposed to be a date?'"

[Speed dating] "is warped. You can't get to know someone in seven minutes. It's making something efficient that shouldn't be. I haven't done any [on-line dating] and probably never will. You can't get the fullness of a person unless you meet face-to-face. I think modern technology is screwing up relationships: it's very artificial and mediated. Living in a big city, for example, sometimes you know who you're e-mailing better than you know your next-door neighbor. That's not natural."

Ideal way to meet people? "Ideally, my relationships would come out of friendships, or going out with a group of friends, or at a party—that's a method you can kind of trust as opposed to Internet dating, when you can meet a psycho....It is difficult to meet interesting people when you first move to a big city and don't know anyone....I feel like I'm supposed to be dating. Most of my college friends are in serious relationships and some are married."

Best date? "When you have a really, really good conversation with someone."

Worst date? "When you have a great time with someone and thought you really connected—and then they never call you again."

Who pays? "I'm like a starving artist these days. If I were out with a banker, I would be angry if he didn't pay. But if I were out with another starving artist, we'd go dutch. When I'm not a starving artist, I'll pay for anyone."

A major concern when dating? "You have no control over the process. They can just dump you. I think this is particularly difficult for Harvard alumni who are used to a meritocratic view of the world—'If I work hard, I will succeed.' In dating, there is no guarantee. Maybe that's what prevents me from dating—I don't want to deal with that kind of failure....

"There are too many opportunities and options out there for Harvard graduates, and knowing that can prevent us from making a commitment—to a city, to a career, to a person—because everything seems so open and possible that we are always thinking, 'There must be something better out there.'"

What do you want from the dating process? "To find someone to connect with and see what happens.... Even if there is no great physical attraction, you may have found someone who can be a good friend—and that's just as successful.... All of us do have this hope of meeting someone who will knock us over, but maybe that's not really realistic."          

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