July 2007

Friend with Benefits: someone you know, genuinely like, and will hang out with during daylight (sober) hours but isn’t relationship material so you don’t date but when the moment strikes you right (perhaps you’re drunk and horny and he or she happens to be in your presence ) you hook up, on occasion

Fuck Buddy: someone you hook up with but don’t really know (and don’t care to know well) and call drunk when you realize he or she is your most viable option for sex for the evening OR someone you don’t particularly like but the sex is too good to resist

Boy/Girlfriend Stand-In: someone who is there for you whenever you need a body to go to a movie with, or move a sofa, or bring you soup when you’re sick, but isn’t getting any from you and you know that he or she desperately wants to sleep with you which is why he or she is putting in the effort and the time

The point of this post: my ex (once removed) was each of these at one point (over the course of 6 years).

When we first met at work, we “greatly disliked” each other. He was the gregarious, frat boy who skirted through college on a fluff major (aka marketing) and I was the anal-retentive, Type-A overachiever who would not help him during training, even though he was my partner. Everything changed once I realized that training had absolutely no bearing on my career and he was an amusement ride of fun.

He started out as a Friend with Benefits. That was inevitable since we were housemates and although we didn’t have intercourse while living under the same roof, I slept in his bed on a regular basis. Girls love to do because it makes us feel safe, warm, and fuzzy and guys like to do this in hopes of having sex.

Then he got a girlfriend, and my benefits ended. Which pissed me off (hence me not particularly liking him) so we became Fuck Buddies. This continued after he broke up with his girlfriend but then I got a boyfriend (J).

I broke up with J, and we transitioned from Fuck Buddies to Friends with Benefits. After I realized he wanted more than just sex, I refrained from having sex with him, at which point he became the Boyfriend Stand-in. Enabling a person to be a stand-in in your life is a truly shitty, selfish thing to do. But I loved him (even though true love is a completely unselfish act) and wanted him in my life and so it continued until he told me he thought was should date and pursue a relationship – I remember every detail of the evening that he brought this up and I have a shoddy, borderline Alzheimer-like memory. It was a Sunday night. He showed up at my apartment. He had candles and flowers and music and I before he could even ask, I told him not to, because he wouldn’t like the answer.

Telling someone you love them and want to be with them when you’re not sure if the person feels the same is one of toughest things to do in life. It takes guts to put yourself out there. It’s also tough to hear no, but two weeks later he asked again, and this time I said okay.

When I agreed to go down the rabbit hole, I did so with blind, wish-for-the-best optimism, the kind I assume most people who walk down the aisle embrace. I thought, “Maybe this can work.” On a selfish level, I wasn’t ready to lose him and knew that I would if I said no. I also knew that if the relationship didn’t work out (which meant we didn’t get married and spend the rest of our lives together), there would be no friendship afterward.

In the back of my mind, I always knew it wouldn’t work. After a few months of dating, a little voice crept into my head, telling me the relationship wasn’t right. And the voice got louder and things started happening, like me having panic attacks when we talked about engagement rings and houses or me noticing other guys. And we finally broke up.

When I look back I don’t think, what if we hadn’t of slept together, would he still be in my life? No, we slept together for a reason. We had some of the most amazing, wake-up-the-neighbors, call-the-cops sex. We literally learned how to be great sexual partners, because we had an incredible amount of trust between us. We picked each other up during some tough times in our lives. We were there for each other. But our friendship was also immature and childish, and we did a lot of stupid things together and we finally outgrew “us.”

What I learned is that the Friend with Benefits, the Fuck Buddy, and the Boyfriend/Girlfriend Stand-In are double-edge swords (and illusions). You may think you’re getting something good out of it, but when you fill your life with one thing, you can prevent something that you really want from entering.


prologue: a cheap and easy way of outlining a backstory so as to not bog down the first chapter with too much detail

Prior to my relationship with Dexter, I had said “I love you” to two other men (besides my father). The first time was said in a state of guilt and the second was said in a state of denial.

The first was to John. I had met him at an alumni homecoming party. He was several years older than me. We were introduced by a mutual friend. We got on the topic of jobs and he said he was an attorney. I looked him over thoroughly and replied, “I don’t see any scales.”

He looked like Mr. Big. I told him he looked like Mr. Big. He laughed and asked if that was a compliment. I said “Definitely, he’s a huge hit with women my mom’s age.” We didn’t stop talking until midnight when we ended up at his hotel room. At first, he turned down my advances for sex. He said he didn’t sleep with girls he barely knew. The only men I’ve found this to be true of is by-choice virgins. Ten minutes later he was knocking on his friend’s hotel room door for condoms.

The next day he dropped me off at my hotel. I jumped out of the car and said something like, “It was fun.” A few days later I got a call from him. He got my number from his fraternity brother, who got my number from my friend. From that point onward, he was in full-on hunter mode.

One of the qualities I was initially attracted to was his ability to debate. That was also the reason I dated him for as long as I did. Over the course of 9 months, I must have tried to break up with him at least a dozen times. Somehow he always talked me out of it.

At the time I started dating him, I was 24 and very unsure about a lot of things in my life. Uncertainty is bad place to start a relationship. It makes it easy to latch onto to whatever “solid” objects appear.

I was also traveling a lot for work. He would get very upset when I didn’t “check in” with him. One weekend I decided to stay in Chicago and hole myself up in my hotel room. I was studying for the GMATs and didn’t want any distractions. He showed up at my office Friday afternoon, unannounced. He decided to fly in and “surprise me.”

There were other things he did, in the name of “love” or “concern.” I couldn’t talk to another guy without him getting jealous. I couldn’t go out and get drunk without him becoming concerned about my well-being. I couldn’t workout without him wondering who I was trying to look good for. The little things that were somewhat endearing in the beginning became more and more oppressive. Our arguments became more frequent. He was jealous of everything and everyone. The more he tried to control, the more I wanted to rebel. Finally I did. I cheated on him. I was in San Diego for work and I met a 20-year-old surf and ski instructor.

When I came back into town, he knew something was up. The fact that I hadn’t “checked in” gave him cause for concern. The interrogation began. I was sitting on the couch, with him hovering over me. I am a poor liar. I broke down and admitted I had kissed another guy. He became very angry. He turned over the coffee table and threw things against the wall. In that moment, all I felt was fear. And then he started crying. That’s when I told him I loved him.

Fear and guilt are two powerful emotions. He became very adept at employing them together. Whenever I was at his house, I felt the need to comply to his likings: to clean and maintain the house meticulously, to cook the meals he liked, to play the music he liked, to fold the towels the way he liked. A turning point was reached one night after work, after we had gone for a run. I got in the shower to wash off and a minute later he threw back the curtain.

“You’re not going to offer to make me dinner?”

“Excuse me?” I was standing there wet and naked.

“You know I’m hungry.”

I do not consider myself a pushover. Nor do I consider myself a submissive person. I would say that most people who know me consider me anything but. And yet somehow I became that. The breaking point came when we were in bed one night and my best guy friend (the second man to whom I would say “I love you”) called my cell. John became extremely angry. His hands ended up around my throat and he started to choke me. And then he let go. I was in my own version of sleeping with the enemy.

Certain things are very easy to see when you have the clarity of mind and perspective to do so. I know that jealousy is simply the expression of insecurity. And individuals who try to control and exert power over others are not powerful. My own insecurities and lack of relationship experience enabled this relationship from the beginning and it is not surprising that my next relationship would be completely opposite from this one.

redo: the act of starting over again when you’re not pleased with the outcome of the initial attempt

My mom taught me two things in life: 1) never depend on a man for financial security and 2) never marry a man who cannot provide for and tend to the family. I used to think these two points were in opposition with each other. Now I understand what she was saying: relinquishing your financial security to another person is tantamount to handing over your personal independence – your power of self. The second point was made as a testament to moms: it’s a full-time job, being pregnant and raising children, and men need to step up to plate, not simply as providers but as active participants in parenting. She also said you should only marry someone who brings as much to the table as you do. Otherwise the relationship is doomed.

Over three years ago, I met the man I thought I’d marry. Dexter was everything I wasn’t and everything I needed. I was 27, he was 32. He was separated from his wife. I was living with my boyfriend at the time, too chickenshit to end it. We met at a work happy hour. I was smoking a cigarette, something I did at bars when I was drunk and bored. We started discussing the merit of hedonistic investing. He owned stock in Phillip Morris. I said I would never invest in tobacco, or any other industry that was detrimental to human lives. He laughed obnoxiously and said he loved making money off of hypocrites like me. He didn’t smoke. I finally stopped.

By the end of the happy hour, Dexter invited me to continue the evening at another bar. He was already well past the point of sobriety. A partner standing next to us interjected with a “Maybe you should go home to your wife.” He wasn’t wearing a wedding ring. He wasn’t acting like a married man. I declined and went home and called my boyfriend who was in Texas for work.

The next morning Dexter pinged me on IM: Good morning, Dollface. We started chatting. Just banter. Nothing serious. Every morning from then on, as soon as I logged into my computer, I would get a ping from him that started with: Good morning, Dollface. Finally, after week, I asked him over IM the question I’d been wanting to ask him ever since the happy hour:

What is your marital status?

You really want to know?


Ok. I’m separated. My wife left me two months ago, right before Christmas. Three months before that, my wife was pregnant and went into premature labor. I was here in DC. She was in Scottsdale. I got on plane and made it to the hospital in time to hold my 24-week old twin sons in the palms of my hands before they died.


From then on, he laid it out there for me. How his mother passed away the year before, with him going through her tax records to discover she only made $16,000 a year. How his dad left him, his mother, and his younger brother when he and his brother were just toddlers. How he grew up in a trailer park. And resented his mother for working all the time and never being able to provide the things all the other kids had. How he told his mom at the age of 6 he would become a millionaire one day. How he worked 3 jobs and gave blood plasma as often as legally possible to pay for college. How he graduated at the top of his class and landed a high-paying job. How he started and sold his first company several years later. And how became a millionaire before the age of 30.

He was a self-made man. Something I utterly admired. Everything in his life he had worked for and achieved on his own. He had earned it.

That was the beginning of our relationship. That’s the beginning of my story. I should have started with this as my first post but it scares me to put it out there because I know what’s yet to come. But I’m going to do it anyway.

honeymoon period: the time at the beginning of a romantic relationship marked by Utopian-like bliss

I fear the honeymoon period, for the same reason I will never try cocaine. It’s highly addictive.

Sometimes I long for the honeymoon period of a relationship, merely because the state of “falling in love” is so deliriously amazing. Kissing feels like a million little butterflies fluttering underneath your skin. Sex is a gluttonous feast of 3am and 3pm rampages – anytime, anyplace, anyhow. Your future is bright and endless with possibilities, and your job, your friends, your family, your life all seem to fade into a barely detectable backdrop of sights and sounds. Nothing else seems to exist and everything seems to levitate to new highs. Driving in the car, going to the grocery store, sitting on the couch watching TV on a Friday night all seem to be new sources of pleasure in the company of your fellow honeymooner.

Forget cocaine. Pass up the alcohol. Eschew gambling. Fall in love!

And then find yourself a good Honeymooners-anonymous support group. Why? Because with the honeymoon period comes a state of blindness (akin to a skark’s feeding frenzy, during which sharks either roll their eyes back into their head or a nictitating membrane closes over their eyes like an upside-down eyelid). During the honeymoon period, DO NOT:

  • move in together
  • make any large purchases together
  • go to Vegas and get married
  • get any tattoos with the other person’s name or picture

Wait the requisite 6 months for the honeymoon period to wear off, and if your love’s “quirky little traits” are still as endearing and little as ever, you can safely assume you’re operating with some sense of rationality.

soft landing: the act of avoiding breakup postmortem by seeking out another relationship prior to the termination of the known-to-be-doomed relationship

The soft landing is a mirage, one of those seemingly good solutions to an unpleasant experience that inevitably comes to bite the enactor in the ass. After attempting the soft landing myself and crashing with a cacaphonic thud, I now watch those who attempt it with the same silent pity as I do whenever I see a Jackass stunt performed.

My soft landing was a result of entering a relationship with my best guy friend (BGF). I knew it was destined for failure and yet I proceeded anyway: my BGF was unrelenting, the sex was amazing, and I loved him, in a best guy friend kind of way. Approximately (8) months passed between the time I started to contemplate a breakup and the day I ended things, which coincidentally was (2) days before I hooked up with the man I had spent the last (4) months flirting with at work.

My soft landing turned into a 3-year relationship that ended with several betrayals of trust (on both sides), a never-to-be-used prenup and a returned engagement ring amounting to the equivalent of a sizable down payment on a house, and me learning that the “easy way out” is never easy.

So two reasons to avoid the soft landing?

1) It’s not fair to the other person. Don’t drag him or her along while you search for the bigger and better deal in order to circumvent being alone or to continue the benefits you reap by staying in the relationship.

2) 9 times out of 10, people will soft land into a relationship that is a reaction to its predecessor. This is due to a lack of perspective and clarity, which only comes from having some time on your own to contemplate what you really want.

Bottom line, you want a soft landing? You’re better off playing seesaw with a bull.