Length of Relationship: Three years
As you can see, I was a Serial Monogamist, with the condition at its peak between ages twenty-three and thirty. During that seven-year period, I dated four girls and was single for four months total, an average of five weeks per breakup. Like a monkey afraid to let go of one branch before grabbing the next, I swung from girl to girl, often having my next love interest in sight before the present relationship ended.
I became this way because I was the classic “Nice Guy.” Nice Guys only date seriously. They are not the type to seduce a girl at a bar and take her home to fuck (not least because we don’t “fuck”; we “make love”). Nice Guys don’t “pick up” women. Instead, we meet them through a mutual friend or an adult learning class and send respectful Facebook messages asking if the girl would like to get dinner, or whatever, at a time totally convenient for her, if it sounds fun, NO PRESSURE. And if a Nice Guy succeeds in getting a date, we immediately aim for a relationship, not a fling. A drunken makeout? Not without a promise ring, thank you very much.
Once I had a girlfriend, I’d usually keep them for a long time, because Nice Guys make great boyfriends. I rarely raised my voice, didn’t complain much, always remembered birthdays, gave massages, and got along with families. I preferred monogamy and never longed for the days of being single. Those days meant talking to strangers—I hated those days.
So what’s wrong with being this fantastic-sounding Nice Guy? We’re more concerned with seeming “nice” than actually being kind. Being nice means behaving in a way you think will make people like you. Kindness means being emotionally honest, even if it will make someone angry. The Nice Guy isn’t good at being emotionally honest, and I was a prime example.
Much too worried about what other people thought of me, I wouldn’t break up with a girlfriend when I wanted to because that was “mean” and I couldn’t bear the idea of anyone not liking me. This is how you end up saying things like “I just want to get set up in New York on my own before you come.”
If, on the other hand, my girlfriends wanted to break up with me, I’d try to convince them to stay, no matter the state of the relationship, because getting dumped felt like a statement about my inherent worth. I’d avoid or quickly diffuse confrontation, rather than solve the underlying issues. Being in a relationship was more important than being in the right relationship.
So, that’s the problem with a Nice Guy. But how did I become one? How does anyone develop a definitive and crippling personality trait? Middle school, of course.
* * *
As a teenager, one of my nicknames was “Porcelain Baby Matteson.” Puberty didn’t hit for me until almost eighteen, so before college I weighed less than 130 pounds, was hairless from the neck down, and sported the smooth, youthful face of a wet porpoise. Friends would greet me in the hall by saying, “For three easy payments of $19.99, you can own your very own Porcelain Baby Matteson, complete with sun parasol.”
While this weak, miniature body was good for a laugh, it wasn’t great for my confidence, especially when it came to women. I wasn’t terminally shy and I did have friends, but the idea of interacting with girls romantically terrified me. To me, sex and dating were like going to the moon—I knew people had done it, but I didn’t understand the science behind it and part of me believed the whole thing might be a hoax.
Instead of asking a girl out, which would insinuate I liked her and saw her in a sexual way (disrespectful), I became the guy who made my friends’ girlfriends laugh and then played video games in the basement while they made out. The guy who saw an invitation to study with a girl as that and only that. Too “nice” to ever make a move, I watched the jerks get the girls.
I first noticed the Jerk-Gets-the-Girl phenomenon in seventh grade, when every day in the halls I’d see some boy snap a girl’s bra, plucking the strap so it made a loud Slap! Why were these girls letting the boys do this? Why weren’t they reporting this behavior to the principal, the police, or the CEO of Victoria’s Secret? Somebody?
The girls didn’t even seem to be offended by this entry-level S&M. In fact, the boys doing the snapping were getting the girlfriends and, if the legends were to be believed, doing something to them with their fingers EVEN MORE disrespectful than the bra snapping.
How could girls like these jerks? I thought. Why aren’t they drawn to me, the nice guy who respectfully ignores them?
At the time, I assumed girls looked past me because they had an inherent sense I’d be insufficient as a boyfriend. Much later, I realized that while bra snapping was a disrespectful and juvenile interaction, it was, at least, an interaction. And dating requires interaction.
In order for me to make an advance on a girl, I would have needed her to write me a letter (preferably notarized) explaining she liked me and was granting permission to kiss her. And even then I’d want to have my lawyer present at said contractually agreed upon kiss.
Things didn’t get better in high school as I maintained my distance from women out of respect (fear). The closest I came to a relationship was an ongoing friendship with a girl I had a massive crush on. Sara smiled at me a lot, touched my arm sometimes, and laughed at my jokes, but, as one of the nicest people in school, she kind of did those things with everyone. I hid my feelings for her because I didn’t want to be the idiot who mistook general kindness for a sign of interest. Oh, she said hello and treated me like a regular human being—I could have sex with her!
Sara and I hung out a lot the summer after our senior year. One night, propped up by liquid courage (Dr Pepper—I didn’t drink in high school), I asked if she’d like to go up to the reservoir and listen to music. While this may sound innocent enough, people didn’t go up to the reservoir to assess the quality of the town’s drinking water. This was our “makeout point.”
“That sounds great,” she said.
“Cool, yeah, whatever, let’s do that, just an idea,” I said, hoping to convey I made out with girls all the time, rather than never in history.
I stayed silent as I drove up the winding road to the reservoir, afraid saying anything could cause Sara to change her mind. We parked and gazed out at the beautiful, clear night. The lights of the city stretched out below us, a mirror of the stars above.
To PERFECTLY set the mood, I put on a Dave Matthews Band CD (oh, everyone liked them back then, leave me alone), and for the next two hours we got buuuuuuusy . . . discussing various topics like our favorite foods. Why selfishly make out, when we could do humanity the service of deciding the pizza vs. cheeseburger argument once and for all?
Yes, all signs pointed to Sara being interested in me, but she hadn’t sent me that notarized letter saying it would be okay for me to kiss her, so I was still nervous. She was so close I could smell her cherry ChapStick, but the three feet between our lips might as well have been a million miles. How would I get from here to there? The idea that I could just lean in and kiss her was ludicrous—she’d see it coming. No, I needed a ruse of some sort. Maybe I could propose a short-distance staring contest? Ask to practice CPR? Offer her a taste of the gum I was chewing?
I thought and thought and thought, but I could not come up with a “move.” How did people do this? How was the human race thriving on Earth when kissing, forget full-on mating, was impossible?
“We’ll need to leave pretty soon,” Sara said near midnight, “so I can get home before curfew.”
She may have hoped a deadline would spur some action on my part. It did not. Instead of kissing her, I immediately started the car.
“Well, we better get you home, then!” I said, relieved I no longer had to sit there failing.
I never did kiss Sara, or anyone else, during high school. On my personal map of life, sex was a blank space where, instead of information, it just said, “Here Be Dragons.”
* * *
Things took a turn for the better after I left home, thanks to the magic of college orientation. At the new school I was a blank slate, no longer Porcelain B
aby Matteson, the guy who hadn’t kissed a girl. (I still somewhat resembled a porcelain baby doll, but at least no one knew that was like my thing.) It also helped that for the first two weeks of school, we were all going CRAZY. There was no parental supervision, no curfew, and a ready supply of alcohol. It was like taking a bunch of rabbits in heat and throwing them into a pen together. And also those rabbits are drunk on Captain Morgan.
During this perfect storm of anonymity and promiscuity, I met my first girlfriend, Maria, a pretty midwestern girl. We were just friends for a few weeks, leading me to assume I’d be playing my normal supporting role with little screen time and almost no dialogue, but one night she asked if she could come to my dorm room to watch a movie.
Because my only furniture, an inflatable chair, couldn’t hold two people, Maria and I had to lie next to each other in my tiny single bed as we watched the film Tommy Boy (Do I know romance or what?). I couldn’t believe it. At college only a month and a girl was IN MY BED and our LEGS WERE TOUCHING. Not quite a notarized letter, but even I saw this as a green light. It still took all the way until the credits for me to do anything, though. As the film faded to black, I knew I was running out of time, so I abandoned any hope of pulling off a “move,” practically flopping on top of her as I pushed my lips toward her mouth. To my amazement, she kissed me back. Turns out desperation can be a move.
We became an official couple soon after and I made up for lost time on the kissing front. Maria and I made out whenever we got a chance: between classes, after lunch, before bed, during movies, and when alone in an elevator. Because we were both virgins and not ready for sex, kissing was all we did. We’d make out for hours at a time, until our chins were red and chapped, our hair a mess, and our underwear fully wedgied from dry humping.
After a couple months we’d nearly worn through the crotches of our jeans, so we decided we should go all the way. Losing our virginity to each other, as first loves, felt perfect, but I was nervous. Abstinence-focused Sex Ed had left me woefully unprepared for what happened during intercourse. I barely understood what a clitoris was. I knew it was part of the vagina and if you answered its three riddles it would grant you a wish, but that was about all.
Even buying condoms for the first time terrified me. I worried that Porcelain Baby Matteson would go into the store and say, “One box of sexual condoms, please,” and the clerk would laugh. “Oh, no, I can’t sell you those. Not only are you too young to have sex, but I can tell you’re also not cool enough.”
I put off the purchase until the afternoon of our planned virginity-losing ceremony. Once inside the drugstore, I found the condoms aisle, but actually stopping and picking a brand mortified me, so I kept walking, glancing over as I passed the section, trying to glean what I could. I did this several times, taking laps through the aisle, getting a little bit of information with each loop.
Lubricated? I thought the vagina took care of that, kind of like a self-cleaning oven. Ribbed for her pleasure? Sounds pretty good. Let the condom do some of the work and take the pressure off me.
After a few passes, I picked a box, but I needed to purchase something else, so I wouldn’t look like some sort of deviant only there to procure sex supplies. But what to buy? I was a little thirsty—how about a beverage? I’m just a normal sexually active guy trying to quench his thirst.
I went to the cooler, scanned over my options, and chose . . . apple juice. Yep, I picked the beverage of choice for four-year-olds in order to make my shopping seem more adult. At the time it seemed like a great choice and I strode proudly to checkout thinking, Matteson, you clever bastard, you’ve solved it!
At the register, I found another trial—the woman doing checkout looked like a grandma. Not a normal grandma, either, but a cute one who would go by “MeMa” or something. I did not want to buy condoms from MeMa, but I’d come too far to turn back (I’d already opened the apple juice).
I approached the register and set my products on the counter. MeMa rang up the apple juice first. It went fine. She didn’t suspect a thing. I don’t know how she reacted to the condoms, because as she picked them up I was reading a package of gum and forcing a look of fascination onto my face to really sell it. Huh, only two calories per piece. I would have guessed three.
“Eighteen thirty-six is your total,” MeMa said.
I slid my twenty-dollar bill across the counter, careful not to make any sudden moves, aware “the deal” could go south at any moment.
“And one sixty-four is your change,” she said as she handed it back, playing it totally cool, as if she hadn’t just sold me something that would later be worn on my penis.
“Have a nice night,” she said as I headed for the door.
Lady, I’ve got a box full of condoms and a bottle of apple juice—you KNOW I’m about to have a good night.
* * *
Because Maria and I both had roommates, we checked in to a hotel room for our special night. You’d think that after years of looking forward to sex, we’d rip each other’s clothes off, but we didn’t. Instead, we sat on the edge of the perfectly made hotel bed, both of us fidgeting silently. Some booze probably would have helped loosen things up, but as we were under twenty-one, the daiquiris we’d had with dinner were appropriately virgin.
When we finally got started, it didn’t go smoothly. In the movies, having sex is easy. The guy gets on top of the girl, music plays, just the right amount of sweat appears on their brows, their butts are somehow tan, and they not only orgasm together, but that orgasm provides a clue to the mystery they’re trying to solve.
In real life, we couldn’t even get started. I’d thought it would be kind of like two magnets, that once our equipment got close enough they’d automatically pull together. Nope. I was thrusting blindly, as if I were playing an easy-looking carnival game that is actually impossible. And neither of us knew we could use our hands down there. I guess we thought sex had the same rules as soccer.
Finally, we managed to make it work, but a couple minutes in, Maria mumbled something. I couldn’t make out what she’d said, but I assumed it was something sensual. After all, we were in the middle of some sensual sex.
“What did you say?” I whispered.
“Stop moving. It hurts.”
I froze. We stayed that way, with me balancing on top of her, trying to not breathe, for three or four minutes, before she asked if we could stop completely. I rolled to the side. Had what we’d done counted? Was I no longer a virgin? As I pondered this, Maria started to cry.
“What’s wrong?”
“That’s just not how I thought it would go,” she sobbed. She described what she’d expected, using the word magical more than once. I told her it would get better, reassuring myself as much as her.
The next morning, with the pressure of the first time gone, we had a much more successful go. But we did make one rookie mistake—we’d forgotten to put out the Do Not Disturb sign, probably because we’d never done anything in a hotel room worth disturbing before.
Right in the middle of our beautiful (awkward) deflowering, we heard a knock, followed immediately by the door opening. In walked a woman pulling a vacuum behind her.
“Please don’t come in, we’re busy!” I yelled. I would have been less embarrassed if she’d caught me chopping up a body.
“Sorry!” she said as she dashed out of the room. After the trouble of getting a hotel room, we were still walked in on.
Despite the interruption, we finished the deed. I don’t know if it was magical, but there wasn’t any crying, so I considered that a win. I was grinning for the rest of the day and wanted to stop everyone I passed and say, “Sex sure is great, right? I know, because I do sex. I’m a sexer. Feel free to discuss sex with me.”
Maria and I were nearly inseparable throughout the rest of college. We did a semester in Paris together, a spring break in Cancún, and alternated Christmases at each other’s houses. It was a great four years, but as graduation approached we realized we hadn’t ma
de a plan for how we’d be together postcollege. She was moving back home and I wanted to go to Alaska to work for the summer. Though it was clear we would break up, we decided not to do it until the end, so we could enjoy our last weeks of college together.
The morning after collecting our diplomas, we hugged goodbye as her cab idled in the street. The hug lasted long enough to make me wonder if leaving the only person I’d ever loved was the right decision. As her cab pulled away, she waved out the window and the tears that had been threatening to fall bullied their way out of my eyes.
Though I had a wonderful summer in Alaska, I disliked being single again. Splitting up had felt like the right thing to do, but I missed Maria and the intimacy I had with her, missed the validation I got from having a girlfriend who told me she loved me. It took more than a year to find my next girlfriend (The Slump) and I hated every minute of being single. I didn’t know it at the time, but this was the beginning of the Nice Guy Cycle. My self-worth became so tied to having a partner that being single made me feel like a loser and getting dumped didn’t mean one person didn’t love me, it meant I was inherently unlovable. Thus, why I hung on to my relationship with Kelly, the Manic Pixie Dream Girl, so long.
But now I wanted to stop the Nice Guy Cycle. No more jumping from relationship to relationship. No more fear of being alone or hiding feelings to avoid confrontation. I wanted to have independent self-worth derived outside of a relationship. I had no idea HOW I would accomplish that, but I knew the first step—getting over my ex.
2
* * *
HOW TO GET OVER A BREAKUP
The small, homemade valentine card, made from red construction paper and white lace, said, “You’re Swell!” on the outside, while a long note from Kelly about how much she loved me filled the inside. I took a deep breath to hold back the tears. What was sadder, that the words were untrue, or that she (and I) had believed them to be utterly true so recently? I tossed the card into a trash bag filled with other mementos from our relationship, a time capsule of happier days.
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