Maybe I don't have a type at all. When I consider my past relationships there is no composite picture. Not that the sample would be considered statistically significant—other than Brandon in high school, I have had only three boyfriends.

My real dating history began my first semester of college at Duke. I lived in a coed dorm, and every night we all gathered in the lounge to study (or pretend to), hang out, and watch shows like Beverly Hills, 90210 and Melrose Place. It was in that lounge that I developed a serious crush on Hunter Bretz from Mississippi. Hunter was scrawny and nerdy, but I was crazy about him. I loved his intelligence, his slow, smooth drawl, and the way his brown eyes fixed on you when you talked, as though he really cared about what you had to say. My roommate Pam, a Jersey girl with big hair, declared my feelings a "total fucking mystery" but still encouraged me to ask Hunter out. I didn't, but I did work hard at developing a friendship, cracking through his shy exterior to talk to him about poetry and literature. I really believed that I was making progress with Hunter when Joey Merola came in for the kill.

Joey was the opposite of Hunter—a boisterous sports guy with a loud laugh. He played every intramural sport in the book and was always strolling into the lounge all sweaty with a story about how his team came from behind in the last second to win the game. He was the kind of guy who was proud of how much he could eat and the fact that he could get by in literature classes without ever reading a book.

One Thursday night, Joey, Hunter, and I were the last three in the lounge, talking about religion, the death penalty, and the meaning of life, the stuff I had imagined discussing in college, away from Darcy and her more shallow pursuits. Joey was an atheist and for the death penalty. Like me, Hunter was Methodist and against the death penalty. All three of us were unclear on the meaning of life. We talked and talked, and I was determined to outlast Joey and end up with Hunter. But sometime after two, Hunter threw in the towel. "Awright y'all, I have an early class."

"C'mon, man. Skip it. I never make my eight o'clock," Joey said proudly.

Hunter laughed. "I figure I'm payin' for it, I should go."

This was another thing I liked about Hunter. He was paying for his own education, unlike most of the rich kids at Duke. So he said good night, and I wistfully watched him amble out of the lounge. Joey didn't miss a beat, just kept yapping, rehashing the fact that we were both from Indiana—just two towns apart—and that both of our fathers had attended Indiana (his dad had been a walk-on for the basketball team). We played the name game and got two hits. Joey knew Blaine, Darcy's ex-boyfriend, from reading the local sports page. And we both knew of Tracy Purlington, a promiscuous girl from the town between ours.

Finally, when I said I really must get to bed, Joey followed me upstairs and kissed me in the stairwell. I thought of Hunter, but I still kissed Joey back, excited to be getting some real collegiate experience. Annalise had already met her now-husband Greg (and lost her virginity to him), and Darcy had hooked up with four guys by my latest count.

The next morning I regretted kissing Joey. Even more so when I spotted Hunter hunkered down in the library stacks, his head bent over a textbook. But not enough to keep me from kissing Joey again that weekend, this time in the laundry room as we waited for our clothes to dry. And so it continued until everybody in our dorm, including Hunter, knew that Joey and I were an item. Pam was psyched for me—said that Joey blew Hunter away and had the cutest butt in the dorm. I wrote to Darcy and Annalise, telling them about my new boyfriend and how I was over Hunter (only partly true) and how happy I was (happy enough). They both had one question: was I going to go all the way with Joey?

I was ambivalent on the subject of sex. Part of me wanted to wait until I was deeply in love, maybe even married. But I was also intensely curious to find out what all the fuss was about, and desperately wanted to be sophisticated and worldly. So after Joey and I had been together a respectable six weeks, I marched over to the school health clinic and returned to my dorm with a prescription for Lo/Ovral, the birth-control pill that Darcy guaranteed would not cause weight gain. A month later, with the added protection of a condom, Joey and I did the great deed. It was his first time too. The earth didn't move during those two and a half minutes, as Darcy claimed it did during her first time with Carlos. But it also didn't hurt as much as Annalise had warned me it would. I was relieved to have it out of the way and happy to join my hometown friends in all their womanly glory. Joey and I embraced in my bottom bunk and said that we loved each other. Ours was a better first time than most.

But that spring, there were two red flags indicating that Joey wasn't the man of my dreams. First, he joined a fraternity and took the whole thing way too seriously. One night when I teased him about the frat's secret handshake, he told me that if I disrespected his brotherhood, I was disrespecting him. Please. Second, Joey became obsessed with Duke basketball, sleeping out in tents for tickets to big games and painting his face blue, jumping up and down courtside with the other "Cameron Crazies."

The whole scene was a bit much, but I guess I would have been fine with his enthusiasm if he had been from New Hampshire or another state with no huge basketball ties. But he was from Indiana. Big Ten country. His father played for the Hoosiers, for God's sake. And there he was, this sudden die-hard "I've liked Duke since the dawn of time and I'm all tight with Bobby Hurley because he once drank at my frat house" kind of a fan. But I looked beyond these imperfections, and we forged ahead to sophomore and then junior year.

Then one night, after Wake Forest beat Duke in hoops, Joey showed up at my place in a foul mood. We began to argue about nothing and everything. First it was petty matters: he said that I snored and hogged the bed (how can you not hog a twin bed?); I complained that he consistently mixed up our toothbrushes (who makes that mistake?). The arguing escalated to more significant issues. And there was no turning back when he called me a boring intellectual and I called him a shameless bandwagoner who actually believed that his painted blue face contributed to Duke's championships. He told me to lighten up and get some school pride, before storming off.

He returned the next day with a solemn face and his scripted "we need to have a talk" introduction followed by the "we'll always be close" conclusion. I was more stunned than sad, but I agreed that maybe we should be having a more diverse college experience, which really meant dating other people. We said we would always be friends, even though I knew we didn't have enough in common for that to happen.

I didn't shed a tear until I saw him at a party holding hands with Betsy Wingate, who had also lived in our freshmen dorm. I didn't want to be holding his hand, so I knew my reaction was only a mix of nostalgia and hurt pride. And regret that maybe I should have pursued Hunter, who had long since been snatched up by another discerning undergraduate.

I phoned Darcy in a rare case of role reversal, seeking comfort from the relationship pro. She told me not to look back, that I had some good, rah-rah college memories with Joey, something I wouldn't have had with Hunter, who would have dragged me down socially. "Besides," she said earnestly, "Joey taught you the basics of predictable, missionary-style sex. And that's worth something, right?" It was her idea of a pep talk. I guess it helped a little.

I kept hoping that Hunter and his girlfriend would break up, but it never happened. I didn't date again at Duke, nor did I through most of law school. The long drought finally ended with Nate Menke.

I met Nate our first year of law school at a party, but for the next three years we barely talked, only said hello in passing. Then we both found ourselves in the same small class—The Empowered Self: Law and Society in the Age of Individualism. Nate spoke in class often, but not just to hear himself speak, as half the people in law school did. He actually had interesting things to say. After I made a decent point one day, he asked if I wanted to grab a coffee to discuss it further. He ordered his black, and I remember copying him because it seemed more sophisticated than dumping milk and sugar into my cup. After coffee, we took a long walk through the Village, stopping in CD stores and used-book shops. We went to dinner after that, and by the end of the evening it was clear that we were going to become a couple.

I was thrilled to have a boyfriend again and became quickly enthralled with most things about Nate. I liked his face, for one. He had the coolest eyes that turned up slightly in a way that would have made him look Asian but for his light coloring. I also liked his personality. He was soft-spoken but strong-willed and politically active in a defiant, angry sort of way. It was hard to keep track of all his causes, but I tried, even convinced myself that I felt the same way. Compared to Joey, who could only muster passion for a basketball team, Nate seemed so real. He was intense in bed too. Although he had had few partners before me, he seemed very experienced, always urging me to try something new. "How's this?" "How's that?" he would ask, and then would memorize his position and get it just right the next time.

Nate and I graduated from law school and spent the summer in the city, studying for the bar exam. Every day we went to the library together, breaking only for meals and sleep. Hour after hour, day after day, week after week, we crammed thousands of rules and facts and laws and theories into our crowded brains. We were both driven less by the desire to succeed than by an all-pervasive fear of failure, which Nate chalked up to our being only children. The relentless ordeal brought us closer. We were both miserable, but happy in our misery together.

But that fall, only one of us stayed miserable. Nate began working as an assistant district attorney in Queens, and I started my law firm job in Midtown. He loved his job, and I hated mine. As Nate interviewed witnesses and prepared for trial, I was relegated to document productions—the lowliest task in the legal profession. Every night I'd sit in conference rooms studying piles of papers in endless cardboard boxes. I'd look at the dates on those documents and think, / was just getting my driver's license when this letter was typed, and here it is, still caught in an endless cycle of litigation. It all seemed so pointless.

So my life was bleak—except for my relationship with Nate. I began to rely on him more and more as my sole source of happiness. I often told him that I loved him, and felt more relief than joy when he said it back. I started to think about marriage, even talked about our theoretical children and where we all might live.

Then one night Nate and I went to a bar in the Village to hear a folk singer from Brooklyn named Carly Weinstein. After her performance, Nate and I and a few other people chatted with her as she put her guitar away with the gentleness of a new mother.

"Your lyrics are beautiful… what inspires you?" Nate asked her, big-eyed.

I was instantly worried; I remembered that look from our first coffee date. I became even more distressed when he bought a copy of her CD. She wasn't that good. I think Nate and Carly went on a date a week later, because there was one night when he was unaccounted for and didn't answer his cell phone until after midnight. I was too afraid to ask where he had been. Besides, I already knew. He had changed. He looked at me differently, a shadow over his face, his mind somewhere else.

Sure enough, we had the big talk soon after that. He was very forthright. "I have feelings for someone else," he said. "I always promised that I would tell you."

I remembered those conversations well, remembered liking the strong, confident way I sounded as I told him that if he ever met someone else, he should just tell me outright, that I could handle it. Of course, I didn't think at the time that it would ever leave the hypothetical realm. I wanted to suck back all my cavalier instructions, tell him instead that I would greatly prefer a gentle lie about needing some space or some time apart.

"Is it Carly?" I asked, a catch in my throat.

He looked shocked. "How did you know?"

"I could just tell," I said, unable to fight back sobs.

"I'm so sorry," he said, hugging me. "It kills me to hurt you like this. But I had to be honest. I owe you that."

So he got a new girl, and he got to be noble. I tried to be angry, but how can you be mad at someone for not wanting to be with you? Instead I just sulked around, gained a few pounds, and swore off men.

Nate kept calling for a few months after our breakup. I knew he was just being nice, but the calls gave me false hope. I could never resist asking about his girlfriend. "Carly is fine," he would say sheepishly. Then once, he answered, "We're moving in together… and I think we're going to get engaged…" His voice trailed off.

"Congratulations. That's great. I'm really happy for you," I said.

"Thank you, Rachel. It means a lot to hear you say that."

"Yeah… Best of luck and all, but I don't think I want you to call me anymore, okay?"

"I understand," he said, probably relieved to be off the hook.

I haven't heard from Nate since that conversation. I'm not sure if or when they married, but I still look for Carly Weinstein sometimes when I'm shopping for CDs. So far she hasn't made it big.

Looking back, I question whether I really loved Nate, or just the security of our relationship. I wonder if my feelings for him didn't have a lot to do with hating my job. From the bar exam through that first hellish year as an associate, Nate was my escape. And sometimes that can feel an awful lot like love.

A reasonable time passed after Nate. I lost my breakup weight, got my hair highlighted, and agreed to a string of blind dates. At worst they were awful. At best, simply uncomfortable and forgettable. Then I met Alec Kaplan at Spy Bar, down in Soho. I was with Darcy and some of her friends from work and he and his oh-so-hip friends approached us. Alec, of course, wooed Darcy at first, but she pushed him my way—literally, with her hand on the small of his back—with firm directions to "talk to my friend." To her, it was the ultimate in generosity. Even though she had Dex, she was never one to turn down male attention. "He's really cute," Darcy kept whispering. "Go for it."

She was right, Alec was cute. But he was also all about image. He was the kind of guy who retires his college cool-boy uniform of filthy, intentionally broken-in baseball caps, fraternity party T-shirts, and woven leather belts, swapping it for his twenty-something urban cool-boy uniform of gripping, cotton-spandex T-shirts, tight black pants with a slight sheen, and loads of hair gel. He told too many "a guy walks into a bar" jokes (none funny) and "I'm a badass trader" war stories (none impressive). When he bought me a drink on that first night, he threw down a one-hundred-dollar bill and told the bartender in a loud voice that he was sorry but he didn't have anything smaller. In a nutshell, he epitomized what Darcy and I call TTH—for Trying Too Hard.

But Alec was smart enough, fun enough, and nice enough. So when he asked for my number, I gave it to him. And when he called and asked me out to dinner, I went. And when he propositioned me, four dates later, ribbed condom in hand, I shrugged inside but said yes. He had a great body, but the sex was just average. My mind often wandered to work, and once when I heard SportsCenter in the background, I even pretended he was Pete Sampras. Many times I came close to breaking up with him, but Darcy kept telling me to give him another chance, that he was rich and cute. Way richer and cuter than Nate, she'd point out. As if that was what it was all about.

Then one night, Claire spotted Alec kissing a petite, somewhat trashy-looking blonde at Merchants. When the girl went to the bathroom, Claire confronted Alec, warning him that if he didn't confess his infidelity, she would tell me herself. So the next day Alec called and sputtered an apology, saying he was getting back together with his ex, who I assume was the girl at Merchants. I almost told him that I had wanted to break up too—it was the truth. But I cared so little that I didn't bother setting the record straight. I simply said okay, best of luck. And that was that.

Every now and then I run into Alec at the New York Sports Club near work. We are very cordial to each other—once I even used the StairMaster beside his, not caring that my face was broken out or that I was wearing my sloppiest gray sweats (Darcy says they should never be worn in public). On that occasion, we made small talk. I inquired about his girlfriend, letting him ramble on about their upcoming trip to Jamaica. It took no effort at all to be nice, another clear indication that I had nothing real invested in our relationship. In some ways, in fact, I shouldn't even put Alec in the serious-boyfriend category. But because I slept with him (and see myself as the sort of woman who would only sleep with someone in a legitimate relationship), I put him in that unfortunately exclusive club.

I review my three boyfriends, the three men I slept with in my twenties, searching for a common thread. Nothing. No consistent features, coloring, stature, personality. But one theme does emerge: they all picked me. And then dumped me. I played the passive role. Waiting for Hunter and then settling for Joey. Waiting to feel more for Nate. Then waiting to feel less. Waiting for Alec to go away and leave me in peace.

And now Dex. My number four. And I am still waiting.

For all of this to blow over.

For his September wedding.

For someone who gives me that tingly feeling as I watch him sleeping in my bed early on a Sunday morning. Someone who isn't engaged to my best friend.