Diary of A Serial Dater

 I am trying to get over a person that I knew briefly, and fell head over heels for, and suddenly realized I never knew. I know how that sounds, but I mean it in the literal way. I was unknowingly dating someone with Manic-Depression. (Please note: untreated, unacknowledged Bipolar Disorder is much different than someone who is currently seeking treatment. I am NOT saying that people with this disease are insane or dysfunctional.) 

I had just begun my job as a barista. When he walked in, there was an instant attraction between both of us, and I turned into an 5 year-old. He was tall, muscular, and with strong, perfect features, with a Robert Redford-like ruggedness .

He fed on my nervousness. He poked fun at me, continuously made me get him things, reminded me what I had forgotten, all with deliberation. It was a game he knew he was winning. He left without asking for my number.

The next week he came in again, and pretended to continue looking at the menu until my line was open. He ordered exactly what I recommended, then asked how late I would be working. He gave me his number and told me to call him when he got off. I was too nervous to bring him his order.

I rushed through my managerial duties (warranting a call from my GM the next morning), pretended I left my ID at home so I could put on makeup, then met him briefly for drinks. Seeing him again, knowing he was waiting to meet me, was flustering and flattering. There was something about his demeanor that made you feel privileged he wanted to spend time with you, something intimidatingly masculine, and being a construction worker, it fit. At the same time, he seemed to know every woman there, which was immediately disconcerting. He claimed they were all friends, and Austin was small, and he had lived here for 10 years blah blah, but there was a coldness in their interactions towards him, that made me wonder how long it would be before things would end (and worried I was already worrying about that). 

I was surprised by how socially awkward he was in conversation. He made some strange jokes, told me he had come by a few times to see if I was working because he’s “creeeeepyyy”, and that I reminded him of a European librarian, which he swore was a compliment.

Our next date was kickball. We acted like playground crushes, awkwardly touching and sharing beers and cigarettes. For being 31, I thought he was a bit strange, but I didn’t mind it. Our first kiss was at a rental store. We shared a love of all things black-and-white, from Frank Sinatra to Alfred Hitchcock. We began spending every day and night together.

Though spending time with him was easy and enjoyable, I constantly felt I was slipping into a weird 50s damsel-in-distress prototype. His masculinity was so overbearing, that I felt weak when I didn’t want to be. He was the kind of guy that dug splinters out of his hands with a box cutter driving 70 on a dirt road (really happened) and I have trouble opening a bottle of wine (also true), at the same time I began to lose myself to him. The only time I saw him nervous was singing “My Way” in a shitty dive bar in front of 10 people. 

One night, he told me that he didn’t want to see anyone else. I had stopped seeing anyone the first night we met, and was all too relieved at the affirmation. Wrapped in scratchy blankets, we inevitably had the conversation every 20-year-old is having, the discussion of “the future”. I was talking about my desire to work in counseling for abused women and children, when he asked me, “What was his name?”

I was stunned. Not many people can read me so easily, and the slight anger I had expressed had tipped him off, and evoked a genuine reaction. I was used to men feeling uncomfortable or pitying, but he did neither.

He continued to ask me his name. I said I didn’t know. He told me that if I found out, to tell him. He had made a “joke” a few days before about having to leave Europe because he had killed someone, and of course I didn’t believe it. He asked if I cared about him, I nodded. He said he cared about me, too. Ironically, if I think about the safest I’ve ever felt, it would be that night.

A sane, non-involved person probably would have never spoken to him again. As a woman who has experienced sexual aggression and been told to “forgive and forget,” and to “move on,” his violent reaction turned into something I envied.

So it went on, passionate and chaotic. We would argue, he would chain smoke, then grab my thighs and carry me to my room. The highest sex drive I’ve ever seen and the best I’ve had. So it goes with crazy men.

Then everything changed.

I had spent the past 4 days sick in bed with him. He had taken me to the doctor, filled my prescriptions, gotten my car serviced, and taken care of me. We had decided to get dinner the night I started feeling better. Over the course of the meal, he began to get more and more uncomfortable, though i couldn’t find a reason why.

We decided to meet up with friends and he began acting strange. He took off his shirt at the bar and began talking loudly to strangers. He took off in my car, speeding to the point that it frightened me and chain smoked two packs in a few hours. We stopped at his house for a second, and when he came back to the car he began jumping around and dancing to a song I played, and wouldn’t get in. By the time we met my friends I didn’t know how to explain what was going on. We ended the night bowling, while he repeatedly said/did strange things (like picking up my friend and biting her arm so hard it left a bruise). At the end of the night, he picked up the tab ($40) on top of the $90+ he had spent all night, even though he had taken out a loan that week to pay the rent.  

When we got back to his apartment, he acted passive and apathetic, and refused to touch me. His room was so cold, I eventually began crying. He moved to the living room couch. I left in the middle of the night. He didn’t try to stop me. 

The next night I ran into him at a bar and he was acting strange again. I went to his house to get my things I had left the night before, and he said he was too tired to drive me home, and meant it. We sat across from each other. He looked miserable. He told me he didn’t feel like he knew anyone anymore, and not in the way an angsty teenager says it. 

It’s a repetitive cycle, but I like to fix things. Unfortunately, fixers are usually broken people, who need distraction from themselves. The Manic said that his hardest relationship was taking care of an ex on suicide watch. He subsequently fell for her, hard. I understand why. It’s giving everything to someone who needs you, but doesn’t want your help. It feels like temporary purpose, temporary sanity in comparison to the loss of theirs, until you realize you’re just decorative furniture. 

This story is a bit too long for one post. A bit too tired tonight, physically and otherwise. The song that follows was on a CD he made. Listening to it now, I hear it much differently. 

I want to start off by saying I did not sleep with, nor did I date, this professor. Clearly, there could be some backlash if I put that out there, and I wouldn’t jeopardize someone else’s career so disreputably. No no, this is solely about my own horrible, creepy crush.

Everyone has experienced a crush on a teacher by now. In high school, everyone was obsessed  with Mr. Health Teacher (who was a a cynical ass, which made him all the more attractive). One of my best friends was deeply in love with her science teacher, who I thought looked like a gnome.

Somehow, being in a school setting, newly-realized hormones, bored… it’s all a perfect combination for unrequited sexual obsession. Therefore, even the most unattractive teachers can get you kinda hot… given the right conditions.

I had always been a bit nervous around semiboner-inducing teachers, but in college, I was faced with the worst hot-for-teacher crush I’ve ever experienced. 

The first day of class, I saw a guy standing outside whom I immediately thought “God, I hope he’s in my class.” Entering, I watched him go to the front and introduce himself. At first, I was excited. I thought, “Awesome, I get to look at this hot, intelligent man every day”. Let it be noted, this was a catastrophic misjudgment on my part. 

What having a gorgeous teacher means is:

1. You can never sleep with them.

2. You constantly fantasize about someone you can never sleep with.

3. You have to see this person nearly every day. 

4. You feel stupid asking questions.

5. You constantly overanalyze responses.

6. Your attempt at perfectionism rises exponentially. 

As much as I like to SAY I’m confident, I’m not, and this situation leveled my defenses. The more classes I took, the more infatuated I became. He was funny, absolutely brilliant, gorgeous, and openly struggled with depression. (In case it’s not clear, that is THE laundry list of qualities I am attracted to.)

So cue the Mean Girls montage, and here I am, pretending that I can’t understand the subject matter because I’m just so dumb!! BLAH hehehe. (Not my proudest moment, I’ll admit.) BUT I did spend nearly every afternoon with him after class. Eventually, the conversation segued into something more personal.

I told him about my pious father, my youth spent in the Church, and how (at the time) being a Christian in a VERY liberal school was difficult, and I felt that my peers’ intolerance in the name of tolerance was hypocritical. (I actually will still stand by that statement, even as an Atheist.) 

In turn, he told me about his experience with Christianity (walking out of service at 8 years-old because he said it was “stupid”) and the many books he’s read regarding the subject. During one of our meetings, I confronted him about his brash remarks on Christianity in class, for which he apologized. Slowly he began giving me more and more literature to read on the subject, which eventually proved a strong case for Atheism. He felt guilty for doing so, but I am still thankful that he opened my eyes to the perspective I now possess, one without overwhelming guilt, without fear of imaginary fires, and true acceptance of all sexuality (specifically my own). 

Side note: I don’t want to say that Christianity is wrong, but wrong for me. Each has his own experience with religion, which was my argument to my professor at the time. However, I found I was forcing myself to believe something I did not in a futile attempt to please others. 

Anyway, it became clear to me that he began picking up on my infatuation… at this point I could hardly look him in the eyes. What was more frustrating, is when I was visibly nervous, he would smile at me. He knew, and he liked it.

Someone once asked me to name the creepiest thing I’ve done to get a guy’s attention, and this would be it: after lending me a book one week, I dipped it in my sink. When I met with him the next week, he immediately asked me if I had been reading it in the bath, which was… yeah. My plan. God, that’s embarrassing to admit. 

 Eventually the semester ended, and I left for winter break. After a few weeks, I received an email from him asking how things were. I ecstatically responded, and suggested continuing to meet up. He agreed, and I told him that because I wouldn’t be in his class, to take my number and call me when he was available.

I never got an email back.

A few weeks later, I ran into him on the street, and he wouldn’t look me in the eye. He asked if he had replied to my email, I said no. He then told me, still looking away, that it would be “better if we just emailed.”

Had I not just met the guy who would become my first (actual) love the week before, I’m sure I would have been devastated and humiliated. Instead, I laughed about it all the way to class. 

I did receive a recommendation from him for grad school, and when I decided not to apply, I opened it up. The letter was strangely self-depricating, and at least 3/4ths mentioned the moment I confronted him about his teaching style, and how it has since caused him to reconsider the way he teaches. I’m not sure how much is flattery and how much is truth, but I was surprised he mentioned it, let alone remembered anything about me, aside from how I constantly tried to make him think of me naked. 

I’m sure I was one of hundreds of girls that attempted to seduce The Professor (he had a bit of a reputation), and I applaud his integrity. I wish I hadn’t been as naive or hormonal, and perhaps I would’ve regarded the advice and guidance that he gave me more then than I do now. I can genuinely say our meetings assisted in changing my life, as I am now much more confident in what I believe and who I am. I hope he is as well.

XX

When I moved to New York City in May, I went through the same inevitable process I experience every time I get that nomadic itch. It follows a basic outline of:

1. Excitement

a. New apartment

b. New people

c. New prospects

2. Fear

a. No knowledge of surroundings

b. No friends

c. No idea where to start

3. Depression

a. Overpriced apartment

b. Still no friends

c. Still no job

It was at this time that I decided to create an OK Cupid account. Pre-To Catch A Predator, the internet was a lame place to find dates, but since has evolved into something much worse. The internet is for lonely fat people, people others would describe saying, “he’s got a great personality, though” or “she’s so great at knitting”. 

But I was in NEW YORK! There were so many men, there had to be some that just didn’t have time for dating between important meetings and switching trains, or whatever corporate people spend their time doing. 

After signing up, I was moderately impressed with the dating pool. There were a lot of “mehs” and a lot of “why nots.” The Lawyer was a “why not”. (It should be noted I did not know his profession at the time, otherwise it probably would have been a “meh” as I tend to go for people with no jobs, or who work in some sort of upscale grocery store or creamery.

When he walked into the bar (I chose a dive-y pizza place with cheap beer), he looked overdressed, and badly overdressed. He was wearing a purple button down with a matching tie, and NICE work pants. I immediately thought “so this is what it feels like to date someone who owns more than one tie.” I also noticed he had red hair, which has always made me think of Pale Force and little angry men.

I immediately made fun of his outfit. He handled it surprisingly well, which I liked. Unintentionally, I had left my wallet at home and had already ordered a drink, for which he gave me well-deserved grief.

We sat down at a crowded table, and he immediately started talking to everyone, which I also liked. They asked how long we had been together, and before I could say anything he said, “5 years.”

After which he began a long story about our relationship history, which follows:

“I was working at the time for this Endangered Animal Association, and she was there. I was immediately enraptured by her, as she was donating millions of dollars to the Save the Panda Fund. I, of course, was dressed up like a panda… I was a mascot. I thought, ‘I can’t talk to this girl dressed like this. So I ran to the bathroom, washed my panda make up off, and asked her out. We’ve been together ever since.’”

Which everyone at the table responded to with “wow” and “that’s adorable.” 

“Yeah, we did break up a few times. She said… well… she said I wasn’t white enough.”

It should be noted that nearly everyone at the table was Latino, Indian, or mixed race, except for me and The Lawyer, who are both very very white.

One of the guys said, “What do you mean he wasn’t white enough?”

“I never said that!”

“It’s OK, honey. They don’t care. She thinks the guys in Vampire Weekend aren’t white enough.”

“I’ve dated a guy from Colombia!”

“She means Columbia University.”

I have to say, I still wasn’t that attracted to him, but it was the first time that someone has immediately played my game… much much better. So when he asked me out again, I said yes. 

We met for ice cream in the park. I had wanted to try The Big Gay Ice Cream truck, and got a chocolate ice cream cone with paprika, which I coughed all over myself. He, in turn, rubbed vanilla ice cream all over his face and let us trade. He told me he had lied and told his boss he was in a business meeting, and would have trouble explaining why he smelled like an 8 year-old. He proceeded, with ice cream dripping all over his suit, to tell me how much he wanted to see me again. 

Yes, he seemed really really into me. Yes, he was doing/saying everything I’ve seen in romantic comedies I hated and secretly envied. Though he still hadn’t done anything less than adorable, I wasn’t interested, and his outright expressions of endearment were pushing me away.

We went on one last date to karaoke. He had even worn a plaid shirt and jeans. Halfway through the night, I had to tell him that I just wasn’t feeling it. He seemed kind of deflated and told me he needed to smoke outside.

Then we never spoke again. As much as I hate to admit this, I guess I learned exactly how superficial I am. Still kicking myself for that one. 

XX

My first serious crush was from 3rd grade to the beginning of 9th grade. Yeeees, it lasted that long, and it is still the most frustrating unrequited loves I’ve ever had. 

It was February 1997, and I had just switched to a new elementary school. We were going around the circle introducing ourselves and BAM. It was him. It was he I had been waiting for my 8 years. It began as an insta-crush (a feeling I have experienced a few times since, and had an almost identical reaction.)

Side note: Insta-crush for me is a crippling, overwhelming, completely unenjoyable experience. I am unable to communicate, I can’t make eye contact, I lose my fat-girl-humor defenses, and if the insta-crush approaches me, I feel like I’m going to throw up. I’m Stan, but Wendy doesn’t like me. 

So, I did the only thing I knew to do… never spoke to him. It was surprisingly easy because in 3rd grade guys were still terrified of women, especially in a Christian school. My crush quickly turned into frustration when I realized he hardly knew I existed, let alone wanted to be my boyfriend.

Come 5th grade, I had become a bitter old hag. I had attempted to befriend him as a tomboy several times, to no avail. Tomboys are athletic, actually enjoy sports, and have little to no interest in boys. I was none of these things, I just dressed like a lesbian because I had spent an entire summer eating trays of Bagel Bites and watching All That. 

I eventually friended several girls in 7th to 8th grade who were ACTUALLY friends with him, but he still seemed completely disinterested. By this time, it was probably clear to him I was crushing, but I felt our potential window was coming to a close as high school approached. I had to take more initiative.

At the same time, I was trying to make it abundantly clear to my friends who knew him that I had no interest in him, and began trying to convince myself. At this point it had been 5 years and I still wasn’t over it. We had gone on school trips together, done track, and had mutual friends. He wasn’t biting and I couldn’t stand it. I would write in my diary “I hate The Crush” or “The Crush’s friends would be so cool if they weren’t friends with him.” Futile devices. There was one time at track when he threw up an entire footlong hot dog and I thought it might be over, but I just ended up feeling sorry for him. 

There was only one thing left to do: listen to songs about unrequited love. “Gone” became my song to The Crush. I would listen to the chorus: “I’ve drove myself insane/wishing I could touch your face” and think no one could understand me more than Justin Timberlake. 

One day, in 8th grade, my friend and I decided to tell him how I felt… through her and me… at the same time. Ambush. Genius. While my friend told him that “someone” had a crush on him and “Gone” made her swoon-y (I wish I could go back in time and hit myself) I said weird goth-y things to him that solidified our separation forever.

This is summary, obviously:

Me: Hey.

Him: Hey.

Me: What’s up.

Him: Nm.

Me: Cool. 

Him: What’s up?

Me: I’m just sitting here thinking about stuff.

Him: About what?

Me: Do you ever wonder if people will come to your funeral?

Him: Um, not rly.

Me: Oh, I do. 

(minutes…)

Me: Would you cry if I died?

Him: Um, I don’t know if I would cry but I would be sad, I guess.

Me: Oh.

Him: This is kinda weird.

And then I immediately got offline and cried. Thinking about that conversation still makes me cringe. 

The next year, we went to high school together, and I got over him by the first day. There was more than 4 attractive guys in my school, I had slimmed down and started doing my hair, and pretty quickly afterwards met The First, making The Crush an instant memory. 

He ended up only dating one girl that I know of, remaining just as mysterious and unattainable.  

I envy that ability to keep mum about crushes, and I miss that feeling of overwhelming devotion. Nothing is quite as exciting as the few decent exchanges between you and your crush. 

XX

My friends and I sometimes play this game, usually way too late in our relationships, where we ask each other a series of “first” questions. First time smoking weed, first time drunk, first time you were felt up, etc. Sometimes the stories are sad, mostly hilarious, and always enlightening. 

Growing up in the church, there was an unusually high amount of importance placed on “firsts,” because, well, it determined how “good” you were. Good girls had no stories, bad girls had many. I spent most of my diary-writing days imagining what my stories would be. Of course I wanted them all to be with a man who looked like Jonathan Taylor Thomas and was deeply devoted to me, and I wanted the kiss to be underwater at camp. (I was obsessed with Mariah Carey’s “Dreamlover” music video from 1998-1999.)

My first kiss was not at all what I expected. I was a good little 14 year-old Christian, and my only knowledge of the art of kissing had come from re-watching scenes from Cruel Intentions and listening to my camp friend’s make out stories. So when I FINALLY got my first boyfriend my Freshman year of high school, we waited about 5 months before kissing, because I was scared shitless. No, I’m not joking.

It was Halloween, and my parents had dropped us off at a haunted house close to the neighborhood. After being slightly disappointed by a few rednecks in bloody masks, we wandered to the park across the street. I was ready for my first, and he was visibly nervous. What follows is a foreshadowing of the nature of our relationship. 

I told him I was cold and so we sat down on a bench. I told him that he should lie on top of me in order to warm me up (super subtle). He proceeded to talk about his favorite foods… I told him to “shut up and kiss me.” He did. I bit his tongue by accident. I hated it. We stopped. He tried to continue kissing me. I played with my ringtones instead. My parents picked us up.

It was 3 months before we kissed again, and this time it was much, much better. After that, we kissed often, and heavily, and continued down the awkward path that is the discovery of your first relationship. 

Of course The First had a huge impact on my life because he was the first, which is why I will often mention him in respect to other areas of my life, and never (ever) stop comparing him to the men I date, even now. He was a perfect first boyfriend, and a horrible first kiss. But that’s the way it goes, I suppose. 

This blog is both a diary and narrative of my strange dating sagas, a way to keep from forgetting the good, the bad, and the certifiably insane. It’s also an exploration of where this strange habit began, as it’s been almost nine years since I have gone without consistently (albeit casually) dating at least one person. My friends make jokes about it, the guys I date often hate it, and I can’t seem to figure out why it won’t end. It is probably equally important to mention that The First was the first—and the last—person I had a serious relationship with, though I have fallen much harder for many men since. I often wonder, as many women do if I will ever be in a serious relationship again. I’m not sure, but in the mean time, I figure I can share all the crazies. 

XX