What I Learned From Revisiting My Three Worst Breakups

"This is a long relationship for you," she said. She had me there. None of my relationships in the past 15 years had lasted longer than five months. But was it really necessary to relive the past, I thought? Shouldn't we be living in the moment, luxuriating in the moonlight and the balmy breeze of early spring and, I wanted to say, thinking about bedtime?

I massaged the fleshy parts of her hands beneath her thumbs. "Shouldn't we be living in the moment," I asked. "Luxuriating in…?"

"Stop," she said. "No moon and breeze stuff." Even though she had an impish sense of humor and skin like expensive Tahitian vanilla bean gelato, and even though she was kind and laughed a lot, she could also be no-nonsense when she wanted to be. She wanted to be.

"How is this any different? How can I be sure it's not going to end like all the others did?" It was a good question. I had considered it during my girlfriend-a-semester college days and immediately after. I had considered it more seriously in my mid- and late- 20s, when no-strings-attached sex seemed to lose its luster and more than a few friends said things like, "It's hard to keep your girlfriends straight." Serious considering had turned to downright pondering in my early 30s, when I actually wanted a lasting romance, but seemed to have difficulty sustaining one. But I was a man, so I moved on, shirked self-analysis. What was the use reliving the past?

By the time I was in my mid-30s, many of my guy friends had serious love interests. The couples hosted brunches together. They confided in each other. They never had to worry about "plus one" invitations. They already had them. Why didn't I? It was a good question—and finding the answer required some introspection. Studies have shown men aren't always the greatest at that—especially after we split up with someone. While women tend to handle breakups worse initially, they also do a better job of recovering. "Men, on the other hand, never fully recover," one summary of the research grimly concludes.

If that's true, it means that I—like most guys—have never fully moved on from my previous relationships, which could explain some of the difficulty I've had settling down. It begged the question: Was it too late, all these years later, to finally begin that healing process? There was only one way to find out, I decided, and it would require revisiting—with the aid of professional help—my most intense and initially promising romances. It would also require navigating around one particularly spooky corner: That's where Carolyn lurked.

I was 24 and working as a cub reporter. She was 30, and the paper's managing editor. She suggested we watch movies together and analyze the story structure, in order to appreciate the power of narrative. After the county fair, she asked me to describe the taste of the cotton candy, the smells (pig, hot dogs, sweat, grass) in the air. I craved her approval. When she didn't give it—"Not detailed enough," she would say, or "too sentimental," or "it sounds good, but it doesn't mean anything," I would sulk.

Sex was great. We laughed a lot. No one appreciated her black eyed peas (and blue cheese burgers and sun dried tomatoes) more than I did. She was smart, fierce, hilarious, and beautiful. She was everything I wanted. Except for the boss thing. I know now—after some years of therapy—that while I did love Sissy, while I did adore her intelligence and wit, and while her brown eyes and tiny frame did excite my most primal limbic impulses, a big part of what was driving our connection was my desperate need for approval. What I see now is that I chose Sissy precisely because she could never totally meet my needs—she was my boss, after all, and I was a cub reporter who made cub reporter mistakes.

"Sissy represented the things you desired at that point in your life," says Karla Ivankovich, a therapist and an adjunct professor at the University of Illinois, Springfield. "She was the boss, she had already achieved the things you were just setting out to do. She was what you hoped to be one day. We seek unconditional positive regard in most aspects of our lives, especially our relationships." By sleeping with my boss," Ivankovich says, I was ensuring I would never get that regard. I emailed her later to ask what I could have done differently. Simple, she replied: "Don't sleep with your boss!!!!" (Exclamation points hers).

Five years and a few romances, later, I met Catherine. Where Sissy was tiny, Catherine was almost six feet tall. Where Sissy laughed so long and loud that people would stare, Sissy cried a lot—talking about her childhood, about a job she didn't get, about a play she had seen (she loved the theater). Whereas Sissy could talk for hours about narrative structure and character development, Catherine told me that "words are so limited." Catherine wore dresses with plunging necklines and sheer blouses. She read one of my stories—I was a writer by then—and she told me I was an artist, like her. She read another one and told me I carried a lot of pain inside, and that she understood it, and cherished it. She said we were wounded soul mates. (Words might have been limited, but I liked the ones coming out of her mouth). She wanted to have sex all the time. She usually cried during, and after, but in a good way.

Oh, and three weeks before we started dating, Catherine had been dumped by a guy with whom she had lived for two years. I found this out a month after she and I started dating. Two weeks later, when I noticed a particularly large T-shirt in her apartment, she said she had been having coffee with him. In her apartment? Yes. Just that once? Why was I being so prosecutorial? Well, I'm curious. "I am seeking closure." "Closure?" "Why are you so judgmental?!" Then she would cry. What I understand now is that while intense sex, raw displays of emotion, and deep, intuitively understood pain of the most personal sort and the almost ineffable soul connections all the above suggests, is nice, it's nothing to base a relationship on. Nothing against romantic comedies or love at first sight, but what I understand now is this: That earth-shaking, stomach lurching feeling you get when you're with someone the first month, or two, or three that you're dating—that's chemistry. There's a reason chemists wear goggles and gloves. Chemicals are volatile. And when closure issues with exes come up, those chemicals are really volatile.

"Wasn't that right?" I asked Ivankovich, proud that now that I was older, I was also a little wiser. Well, yeah, she told me, but there was more: "Frankly," she says, "you were operating with the wrong brain. You got an incredible amount of positive reinforcement because she expressed raw emotion, and there is something to be said about the power that the vagina has on men. The problem is, you didn't take the time to develop a relationship. You engaged with a sex partner."

Nadia found everything I said instructive if not brilliant, and hilarious. She had algae-green eyes, lips like apple turnovers, supermodel legs, and an intoxicating habit of humming and squeezing my hand whenever when I said anything. Nadia had grown up in Siberia, and come to New York City when she was 20 with her two-year-old daughter, $300 in cash, and the name of a lawyer who had a reputation for helping Eastern Europeans with their paperwork, but who ended up demanding Nadia sleep with him.

She refused, took a job as a housekeeper, found a basement apartment in Queens, and saved her money. She had grit. Being with her, I felt like I had grit. Also, that I was a citizen of the world. Also, that I was a hero. I loved that I could help her—with language, and with warmth and kindness, and with love. She needed it, what with her difficult past and ongoing struggles with English. I could save her. I liked being a savior. I introduced her to college basketball and professional baseball, to film noir and to riding bicycles. She told me about growing up with breadlines and secrets. She said "ooof" a lot and I felt strong.

On the other hand, she was still technically and legally entwined with the man who paid her rent and employed her as a part time consultant at his medical practice. "What we in this country call married," a friend pointed out. When I suggested to Nadia a divorce might be in order, given our very real and lasting love, she looked at me. Why in the world would she want a divorce?

"Because of us," I said. "Us is fun," Nadia said. "Yes," I agreed. "But it is more than fun. It is real. It is lasting. It is love." "Vy are you soch a child?" Nadia inquired. Paging Dr. I!

"You got involved with someone who was married," Ivankovich told me. "And to add to that, your hurt little boy found the attention he craved and, rather than share in the wealth of the attention, you focused on receiving instead of giving because it really felt good to be admired and adored. She needed you. And you wanted to be needed."

So I should have been more giving? I should have focused even more on helping Nadia make her way through this great country of ours, and in that way I would have found the love and lasting relationship I deserved, right? Wrong, Ivankovich says. Then what? "Don't get involved with a married woman!" she says.

I had sought approval from Sissy, understanding from Catherine, the power of being a hero from Nadia. And when I didn't get those things—those pure, unreal, impossible-for-any-adult-human-to-deliver-to-another-adult-human things, I pushed, I criticized, I complained, and it was over. So obsessed had I been with satisfying my childish, deep, and yes, dark needs, that I hadn't left a lot of room for getting to know the other person.

I emailed Ivankovich. I had it wired, right? I had it figured out. What I needed to do was simply to work harder at getting to know the person, to focus less on my needs and more on hers. That way, I would get the real love I needed. Wrong again.

"When you spend time seeking approval," she says, "you are not presenting an authentic self but rather what you perceive to be the ideal self—or the self you want others to see. You are putting on an act. Spend more time building a relationship with yourself than anyone else. If you are not happy with yourself, you are more likely to solicit approval or attention from others." (And women do make the same mistake every bit as often we do, Ivankovich says). "Work more diligently on being happy with yourself and improving self-esteem, which will allow you to be a better partner."

That's what I have been working on in therapy the past few years. There, I'm looking at the patterns in all my breakups, the role that I played. I'm trying to not mistake drama for deepness, and need for love. If I had been working on all that years ago, I suspect I might have settled down. I called the woman who smelled like vanilla gelato, aka, "my girlfriend."

I told her what I had learned, how I saw that I always demanded things that no one could ever give, and I didn't want to do that anymore. I told her if I was feeling low, or worthless, I might or might not mention it to her, and I might or might not be grumpy, but the one thing I wouldn't do was blame her, or demand affirmation from her, or start an argument just to distract myself from myself. I told her I had screwed up a lot of past romances, emphasis on I. I told her I wanted to take responsibility for my feelings, that I cared about her, that I loved her. That was my intention. That was what I wanted to do. What did she think of that?

She took my hand. That sounded good, she said. That sounded just fine.

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