OkCupid Chronicles: Embarrassing Tales of Misogyny & Low Self-Esteem

Preamble: The following is one of many accounts of dating from June 2010, when I broke up with my girlfriend of four years, to March 2011, when I met my new girlfriend. For most of this time I had no soul, abused various substances, and only sought sex. This one is about being “on.”

Still living with my ex-girlfriend, fresh from the break-up, I first stalkedOkCupid searching for girls based on how quickly I could get sex.

Soon, I had a target. Her picture was non-standard. She was in weird Halloweenesque goblin makeup. Now, I don’t know why someone on OkCupid would do this unless either 1) they were mentally unstable, 2) they had no self-esteem and thus sought safety behind a persona, or 3) they’re a hipster. Whatever her reason, her other pictures were make-up free. When we talked, I learned she was deeply misanthropic. Combining this with her comfort with first-date sex, I was sold.

So, I met her at a bar. She was cute enough, though slightly resembled ET. She spoke in an overly mannish sardonic fashion barely moving her jaw, much in the way an overweight Goth highschool lesbian might speak. Either way, it’s better than the creaky talk/glottal fry of the current female zeitgeist. More troublesome was the foam of saliva perpetually persisting at the corners of her mouth. I forged on. Seduction was my end-game, for after all, she had vagina and she was someone other than my ex-girlfriend.

We spoke and had drinks. My shoddy and self-serving memory retrieves this exchange:

“Are you ‘on’ all the time?”

Embarrassment. Mortification. Being “on” is a common accusation to a comic, which I still was at time. It confirms every comic’s fear: people find you annoying, not funny.

“I’m just trying to be interesting.”

Now this might have been my fault. At the time I was experimenting with illicit drugs which may have changed my behavior into the suspicious. Who knows? I do not yet have the confidence in my career to me any more frank than this, but I’m sure you can figure out what was going on. No, it wasn’t peyote.

• OkCupid Chronicles: No, a Dominatrix Won’t Have Sex With You

I was able to steamroll ahead and finagled her into going back to her place to partake in some illicit drugs, and she agreed. I was golden, right?

Well, apparently, apartment time does not equate sex time. At her apartment, I looked up music on YouTube while she lay in her bed. She offered me nothing and seemed downright annoyed by me. I guess Iwas “on.” At some point I called it a night.

“Well, I guess I should probably leave.”

“Yeah, you should.”

Even now this response pisses me off. She could have rejected my self-invite. Maybe she just wanted to use me for illicit substances. I didn’t know whether to feel like a piece of meat or a rapist. I got home that night and crawled into bed with my ex-girlfriend who was sound asleep. The couch wasn’t comfortable enough and it wasn’t like she could force me out of the bed.

The next first was the first time I would have sex since my relationship with my ex.

A month after that first date, I had moved into a new apartment, and found a girl on OkCupid who was a fellow comedian. She kind of had this Alanis Morrisette / Jillian Michaels / Jew look to her which, based on the pictures on OkCupid, made her seem kind of cute. She was thick like a porterhouse, but not flabby, short and stout like a roller-derby athlete.

I met her at a bar near my apartment and we hit it off immediately. She was a little “thicker” than her photos. But I was still imagining Shawn Johnson beneath her clothes. Besides, she probably had a great personality. I felt more attractive than her, so I didn’t have to worry about being “on” or coming on too strong. I even told her about my first date with the spit-mouth girl.

We drank until I took her back to my place to–you guessed it–engage in illegal substance abuse. (I have never done drugs, okay prospective employers?)  When I made a move, she damn near tackled me. She removed her shirt.

My friend Ray can be the most offensive insulting person in the universe. He admonished me for characterizing her body with such crass misogyny. Thus, this caveat: my evaluation doesn’t come from hate, it comes from sheer surprise, and the urge to be “on.” That said, this is what I told Ray.

“There was… extra skin. Like she used to be morbidly obese but suddenly lost all the weight. Like a Biggest Loser winner. She resembled a Shar-pei or a folded up parachute.”

I hate having to express disdain for someone else’s body. I myself am a little overweight and very body conscious. According to Wii Fit my BMI is 27.55. I’m not saying this girl has no worth. She was a terrific person who deserves love as much as anyone else. Still, she had a shitload of extra skin which I found to be shocking, and frankly, repulsive.

So, I fucked her.

I laid her on the bed and laid myself on top of her and proceeded to get laid as she trembled beneath me, her legs up around my back looking as if she had fallen into a vat of dough. When I ejaculated (spoiler alert), I looked down on her, panting, dripping sweat onto her, and said the first thing that popped into my dumb head.

“You’re the first girl I’ve had sex with since my girlfriend.”

Right. “Girlfriend.” Not “ex-girlfriend.” Not “that was fun.” Not “that sucked.” Not “where did you get all that beautiful skin?” Just the lamest, most pathetic admission of inadequacy I could muster.

I felt like I had cheated on my ex-girlfriend. I had broken our ex-trust–again. I was somewhere between scum and nothing.

I re-robed and asked the girl to come to the stoop with me to have a cigarette. (Besides the illicit substances that I may or may not have been doing with plausible deniability, I had also re-taken up smoking). She smoked too. We talked about my feelings. How I missed my ex, how I was a mess, a shell of a man, a monster, a pseudo-rapist, etc. Of course she was tremendously sympathetic. She assured me she was just casually dating as well and had also just left a long term relationship.

After a few minutes — and by the way, this is why I am a hideous monster — I was able to convince her to leave, not sleep over — kind of a Wham-bam-I-am-an-empty-shell-of-a-hu-man. Maybe I’m not a monster, maybe I’m just a man doing his best to be happy. I made a vow to raise my personal standards, have a higher opinion of myself, not just throw myself at any willing participant. So, never contacted this girl again, except about a month later, on a random night. But I had a valid reason: I was horny.

“Want to hang out?”

“Sure, guy I had a one-night-stand with a month ago. Let’s do that same thing again! You’re a real winner and definitely not a monster.”

In truth, she didn’t return my text. Good for her.

Evan Jacobs is a 31-year-old schlub who used to do stand-up comedy, excel academically and slay the ladies. These days, between the time he spends trying to publish his novel and teaching at a for-profit Manhattan college, he complains incessantly about nearly everything.

Reprinted from Hypervocal

The OKCupid Chronicles: No, a Dominatrix Won’t Have Sex With You

jeremy brooks

Preamble: The following is one of many accounts of dating from June 2010, when I broke up with my girlfriend of four years, to March 2011, when I met my new girlfriend.  For most of this time I had no soul, abused various substances, and only sought sex. OKCupid conversations will be included with the stories, when available.

Though it hadn’t occurred to me during the relationship, at some point I realized I was sexually repressed. Sure, I had had many partners already — mostly because I had channeled high school frustrations into a never-ending search for validation — but I hadn’t really done that much sexually. I knew about stuff — I had the internet — but knowing isn’t doing.

The girl wasn’t exactly beautiful, but she posted very suggestive pictures, and responded to my message.  She was a dominatrix. I had never tried being dominated. I guess it couldn’t hurt.

I called her one Saturday night around 11 and asked to meet. When she agreed, I figured the deal was done. It was a booty call, right?

NEXT STORY: How I Learned to Stop Being a Hater and Love OKCupid

We were to meet at 2:00 a.m. on Ditmars in Astoria. She walked from her apartment, I from mine; we would meet halfway. There were very few people out except for bar hoppers and a homeless woman rooting through garbage.

“Evan?” The homeless woman said to me.

Oh.

“Jody?” I said. I took a closer look at her. She was overweight, more so than her pictures led me to believe (standard OKCupid etiquette), Indian (I could have sworn she was a Latina by the pictures), wearing taut jeans and a T-shirt with “PORN” written across her breasts. She displayed a sundress.

“What do you think?” she asked.

“Is it from the garbage?”

“It’s free!”

“It’s garbage.”

In Jody’s defense, this particular garbage bag was filled only with old clothes. However, this was not the most auspicious start.

Strange formalities ensued. She hadn’t realized I was her OKCupid date. She thought I was there to sell her drugs. Apparently, the drug dealer was named Evan as well. She sent some texts and made some calls, deliberating until I eventually convinced her to hang out with em. After all, there we were.

“Sorry, I’m on Ambien,” she apologized.

Jerry Maguire flashed through my head. You had me at “I’m on Ambien.”

I took her back to my apartment. We drank. She turned out to be quite, clever, fun, and grew more attractive to me as the minutes passed. At some point, she broached the unspoken.

“So, you’re the kid who wanted to try domination.”

I stammered like Hugh Grant before confirming it. I had just suggested it to get her attention. I wasn’t against it, but it wasn’t like being dominated was a life’s dream of mine. She took it in stride, the got down to business.

“I know it’s your first time. Most of my clients like it when —”

“Clients? You’re like a professional dominatrix?” This had not been explicit online. Many women say they are dominatrices. Doesn’t mean they have fucking clients. What kind of date did she think this was?

“You said you wanted to try it.”

“Not for money! I wasn’t trying to hire you. I just wanted to hang out. Like a date. Like OKCupid.”

She was silent for a second, obviously caught off guard. It was as if I had told her I was high on Ambien.

“Well, I have a boyfriend,” she said. I wanted to slap my forehead. “You’re pretty cute, though, so I’ll do it for free.”

“Okay,” I said, wondering how her boyfriend would end up killing me.

She said she would keep it light. Start off by calling me names. Pig. Dog. Stuff like that. I was already smiling, finding the whole situation ridiculous. Degrading names couldn’t hold a candle to my own (lack of) self-worth.

She told me to take of my shirt. She pinched my nipples for a little bit, and slapped me. I can now say with certainty I do not derive sexual pleasure from having my nipples pinched.

“Maybe I’ll step on your chest,” she said.

“Okay,” I said, keeping my perpetual smirk.

As she started, I tried to prepare myself for death. She wasn’t too overweight, hovering around one hundred and sixty pounds. Still, every time she took a step on my chest all I could think about was how easy it would be for my ribs to give way, break, and puncture my heart, killing me instantly. Instead of killing me, however, she interrogated me.

“What do you want?” she barked at me.

Interesting. People don’t usually ask me that question, as people very rarely care about what I want. So I didn’t know what to tell her, except that I didn’t know.

“I don’t know.”

“What do you want?” I could tell she was looking for an answer, but I wasn’t sure what it was, so I told her the truth.

“To fuck you?”

It wasn’t what she was looking for and it took the wind from her sails. She sighed heavily and stepped off of me.

Thinking back to it, I’m pretty sure the right answer would have been “More, Mistress. I want more.” Or, conversely, an okay answer would have been “Stop, Mistress. I want you to stop.” Either way, it was something she could have worked with. She stepped off me.

“I could hit you with your belt.”

“Uh,” I said while still laying shirtless on my back, “why don’t we call it quits and just hang out for a little bit.”

We actually had some good conversation after that. Most guys who liked domination were men who in regular life always had power over women. This is probably why I didn’t like domination. I don’t think there’s a woman alive who doesn’t have power over me. Be cute and I’ll murder for you.

Jody and I agreed to hang out again. And hey, if I ever wanted drugs, I could buy them from her.

Of course, I never saw her again.

The biggest lesson I took from this is one that I will carry to my grave: A dominatrix doesn’t have sex with you.

SEE MORE:
• Even Stand-up Comics Hate Stand-up Comics

Evan Jacobs is a 31-year-old schlub who used to do stand-up comedy, excel academically and slay the ladies. These days, between the time he spends trying to publish his novel and teaching at a for-profit Manhattan college, he complains incessantly about nearly everything.

Reprinted from Hypervocal

How to Lose a Girl in Ten Semesters

 

Evan Jacobs recalls the one that got away, and how he let her go.

To me, she was Becky. To anyone else: Rebecca. I met her my on first day of college. I turned down a dorm hallway, and there she was, standing at her door, about to enter for the first time. She had black hair with telephone-cord curls, a face as round as a Peanuts character, and a nose upturned like a blunted checkmark. She stood off my shoulder in a cute, gangly body consisting of rectangles. In her lilting Chicagoan accent, she spoke as if we were old friends.

“I think this is my room.”

“Are you Emma Lam from Hong Kong?”

“I think that’s my roommate. I’m Rebecca.”

“Rebecca? I’m Evan. I think I’ll call you Becky. Can I call you Becky?”

“Uh. I guess.”

Now, Becky was resoundingly cute, and I was resoundingly attracted to her, but I had only ever had sex with one person—and I was still with that person. Thus, I befriended Becky in the way I befriend anyone—methodically and psychotically.

We shared two classes, Biology and Calculus, and lived a couple hundred feet from each other, so I always had an excuse to talk to her. Besides, Emma, her bite-sized roommate shipped from China, existed solely to giggle at my antics.

♦◊♦

My doomed long-distance relationship persisted the first few months of college, so any romantic moment Becky and I shared (if there were any) was lost. Still, our friendship grew. We learned about each other. Becky was the oldest of four sisters and a baby brother. Her parents were kind and caring. Her mother once witnessed me hugging her and said, “Take your hands off my daughter.” It was a joke, but she must have seen the glassy sheen of my eyes when I ogled Becky.

Eventually, I gave my girlfriend the ol’ fashioned “Hey, remember when I said we’d be together forever? Yeah, about that…” Then, I had a decision to make. As I’ve brusquely spewed before, I have eternally believed happiness directly increased with the amount of women I bedded. I knew if Becky and I explored a romance, it would go well. I couldn’t foresee a break-up with Becky. So I would wait. Like a horror-film ghost, I had unfinished work.

I told myself it was a good idea. Becky had never had a boyfriend. First relationships are highly caustic and usually terminal. If Becky were to get a boyfriend, she could catch up to my level of maturity, then break up. I would pick up the pieces and live happily with Becky without her worrying about other men.

The plan was perfect.

The plan was also stupid and self-sabotaging. I had sex with one girl that year, in October. Meanwhile, Becky and I got dinner, dyed each other’s hair green (actually, she just dyed mine), smoked weed (actually, the one time Becky smoked, she almost went into a coma), and got piercings (I got two and she got zero).

Over the next year, mostly because I had colored hair, women noticed me more, and before you could say “unprotected sex,” I had had a slew of girlfriends and was rarely single. See: the Kathy story. But as I fornicated and flirted, Becky remained.

♦◊♦

When the world went from pre- to post-9/11 and my third year began, I figured I had waited long enough. Becky would be mine. As soon as she got back from Paris, that is. Becky was taking a semester abroad. In Paris, le café runs hot and les hormones run hotter. She met someone, of course.

“His name’s Jerome.”

“Is he black?”

The second most painful experience is learning the person you love has a significant other. The most painful experience is meeting and genuinely liking that significant other. I met Jerome. I’d date him, too. He wasn’t black. He was tall, skinny, pockmarked, incredibly nice, and a fellow University of Chicago student on the trip with her.

Still, it was part of my plan. I just had to wait. Jerome was the captain of the cross-country team and a likely Rhode’s Scholar. Plenty of girls would tell him he ran like a gazelle and present their heaving breasts to him for suckling. Maybe Becky would grow tired of his skinny frame and yearn for a meaty substitute in the form of me.

They would break up. All first relationships break up. But they didn’t.

We finished our last year. We graduated. I stayed in Hyde Park for a year after college. It was early June 2004, and I was moving to New York City in days. Though I tried to forget it, I couldn’t leave without knowing what could have been.

♦◊♦

Becky and I had dinner together. It was just another time out of dozens. After all, Becky didn’t smoke weed or drink, and I only smoked weed and drank. So, our shared realm was that of meals. Of course, this time, my dinner suggestion was shorthand for “Let me ambush you with a confession of love.” I could see it in my head as we drove to the restaurant together.

“Becky, I love you. Always have,” I’d say.

“I wish I knew how to quit you!” she’d say back.

“I know,” I’d say.

Okay, so that was BraveheartBrokeback Mountain, and The Empire Strikes Back, respectively, but you get the idea.

Dinner progressed normally. Perhaps I pried more than usual. “Does he treat you well?” “Ever wonder if there are better matches for you?” “Ever worry he cheats on you?” “He’s probably cheating on you, right?” “He told me he was cheating. You should cheat on him.” But no, he treated her better than I had the capacity to, it seemed. Still, selfish asshole that I was, I had to say something. After all, I had been there first!

I remember it as if it were in present tense:

We’re parked in the driveway of my apartment building. Becky’s in the driver’s seat.

“Becky, I have something to tell you.”

“OK.”

“I love you. I’ve always loved you. I loved you the day we met. I’m sorry, I know you’re happy with Jerome. But I had to tell you.”

She twists up her face and sobs.

“Evan… why didn’t you tell me?”

“I don’t know.”

“I can’t. Part of me wants to. But I can’t.”

“I know.”

I lean in and kiss her. It’s a soft, five-second, tongue-less kiss and though I don’t realize it, one of the most romantic moments of my life. She’s still crying. I apologize again and say goodbye.

The next time I see Becky, it’s at her wedding to Jerome, three years later.

Becky and I are still friends. We speak once every three to six months. Though I’ve moved on, I know if I had said something earlier, I’d probably be with her now. Of course, that would mean never experiencing any subsequent girlfriends, and, based on the girl I love now, perhaps I made the right choices after all. For now, and forever, the kiss she gave me was enough. Because at least it told me I was brave, I was worthy, and at some point, she had loved me too.

—Photo Samantha Louise Knott/Flickr

Reprinted from The Good Men Project

Chronicles of a Phone Sex Addict Part II

In college, Evan Jacobs—the ‘saddest egotist of all time’—stole his mother’s work phone and retreated to the seedy world of phone-sex party lines. His mom nearly lost her job. Evan got a shrink.

Hi. Uh … I’m Evan.

I’m just looking on here to … uh … huh … get off with someone. I’m touching myself.

Send me a message. Let’s have a fun time.

My loneliness, my lack of social skills, my low self-esteem, can, when left unchecked, completely run over my life and subsume nearly everything. At this point in my life, I’m not sure if I’ve solved any of my problems. But I’ve learned that fees for phone calls to Antigua tend to add up quickly, and it’s much cheaper—and less depressing—to try to pick up women at bars.

When I first discovered phone sex, I was much younger. The problem wasn’t nearly intense enough to be labeled an addiction. It was phone sex with a girl I loved; the long-distance fees were nothing a few months’ work at McDonalds couldn’t cover. I learned actual lessons from that experience: what it means to be a young man coming of age in an atmosphere teeming with sex, and how to prepare an Extra Value Meal.

And then I went to college, struck out with women, came home, got desperate, stole my mother’s work phone, and locked my door for an entire summer.

♦◊♦


♦◊♦

Welcome to Hot Talk, the sexiest party line on the planet. Here you’ll meet real, live, horny girls who can’t wait to talk to you. These girls are wet and hungry for your cock. Touch-tone phones only. International rates apply. Press 1 to accept.

Boop.

This is the main menu. If you are a man looking for a woman, press 1. If you are a—

Boop.

This is the Hot Talk mailbox. To listen to users’ greetings, press 1. To record your—

Boop.

Heavy breathing. Hi, this is Sheila. I’m sitting here … uh … uh … playing with myself … yeah … just looking for some of that big dick. Hit me up.

To hear this greeting again, press 1. To send this user a message, press 2. To listen to the next greeting, press 3.

Boop.

Hi, I’m Sarah. (It was actually a man with a deep voice, posing as a woman.) I just wanna hear some of you guys jerk off. I’m touching myself. I have huge tits. I’m blonde, blue-eyed. I love sucking guys off. Send me a—

Boop.

Hi, I’m Marjorie. How’d you like a—

Boop.

Hi, I’m, uh, just sitting here, huh … uh … touching myself … yeah. And I think that … you should send me … yeah … a message.

To hear this greeting again, press 1. To—

Boop.

Hi, I’m, uh, just sitting here, huh … uh … touching myself … yeah. And I think—

Boop.

To hear this greeting again, press 1. To send this user a message, press 2. To—

Boop.

Please record your message after the beep. BEEP.

“Hi. Uh … I’m Evan.”

♦◊♦

When I say I was desperate, I don’t mean joke-desperate, like, “Oh, my friend can’t get girls.” I mean a perverse, intense, obsessive variety of all-encompassing desperation.

I over-analyzed every interaction to the point of lunacy. Even eye contact—every girl who didn’t return a glance was a rejection, everyone who did was a missed opportunity—which made me the saddest egotist of all time. The thought never entered my consciousness that whatever girl I found in my crosshairs was preoccupied with something slightly more important than a random dude staring her down. Girls existed only to validate me, I thought, and they never did.

It’s not that I got zero attention. I did, in fact, sleep with one woman in the very beginning of freshman year—and then struck out about 30 weekends in a row after that. By the summer, my confidence had completely eroded to the point where it took the following year to recover—and jeopardized two otherwise half-decent relationships.

Back home near Philadelphia, my mom was kind enough and nepotistic enough to procure me a job at her company, a market-research firm for pharmaceuticals. At the time, cell phones were on the verge of becoming ubiquitous. I had a crappy Nokia (has anything changed?) with a black-and-white display and a battery that fell out if you brushed your pocket or had an errant heartbeat. My mother, on the other hand, had a StarTAC—the most advanced phone I had ever seen.

It quickly occurred to me that because the company was paying for my mom’s cell phone, they would probably approve all her charges without actually checking the records. Considering my long-distance problem from two years before, I was wary to use the house phone again, lest Mom find any large charges. But the company was paying me so much for so little, so I figured they probably didn’t care about large charges. They’d assume, because my mother was vice president, whatever she did was kosher.

I Googled “phone sex,” and after wading through pages of credit-card-only results, I found something intriguing: party lines. I’d be talking to real people—not people who were paid to talk to me, which wasn’t attractive. The crux of the issue wasn’t just orgasm—it was validation from another human being.

So late one night, I went downstairs, found my mother’s purse, and snatched the StarTAC. After the moment I came, I was hooked. I was stealing the phone every night and making calls. After two months, I went back to school and braced myself for the worst.

A month passed. No angry calls. I had gotten away with it. The StarTAC was safe in Mom’s purse and I was safe at the University of Chicago.

Wrong.

♦◊♦

The call came in October.

“Hello?”

“Evan, this is your mother.”

“I know, Mom. What’s up?”

“Evan, were you using my cell phone to call phone-sex lines.” It wasn’t a question.

“Um … what?”

“There’s a 3,000-dollar phone bill for June and July on my cell phone.”

“Really?”

“Yes, multiple calls to Antigua. Evan, do you know how much it costs to make international calls? This isn’t good. I found out about this at work. I had to explain myself.”

“You did?”

“I could have been fired, Evan. Did you call those numbers?”

“Well. I, uh … I … well … kind of.”

“Evan.”

“Mom, I’m really sorry. I was really lonely.”

“Evan. Your father and I are really disappointed in you.”

“I know. I can pay it back.”

“Damn right you’re going to pay it back. It was 3,500 dollars.”

“OK. Just take the money I made over the summer.”

“Your father and I think that maybe you should come home for this semester.”

“No! I don’t think that’s the best idea.”

“Then you need to see a psychiatrist.”

“OK. I can do that.”

I hung up the phone. Then I got really, really high.

♦◊♦

What was wrong with me? Why couldn’t I just be involuntarily celibate like so many of my friends? Why couldn’t I just jerk off like a normal asshole? How did this lecherous old pervert take over my mind and personality? Were other guys like me? Was I a sex addict?

I didn’t know. I still don’t know. But I felt awful. I felt like a monster. I believed that a mother would be right to pull her child to her side when I passed by them on the street, I believed that any girl I saw covering up her cleavage was doing it because she knew the real me, I believed that with this in my history I would never find love, because no one would ever accept me. Searching for this kind of validation on the phone had had the opposite effect: my self-confidence was in a worse place than it was before.

The psychiatrist was a young, bald man working on Michigan Avenue in downtown Chicago. I had seen psychiatrists before, but it had always been for my ADHD. This was the first time I had ever gone in for something more, well, problematic.

“Hi, I’m Dr. Denson,” he said. “Tell me why you’re here today.”

“Hi. Uh … I’m Evan. I’m here to … uh … huh. Well, I spent 3,500 dollars on phone sex this summer.”

♦◊♦

We talked about that. But quickly our sessions just turned into discussions about which of my medications were working and which were not. We never actually delved into the roots of my addiction issues. I’m working on these issues with my current therapist, but much work remains.

Still, I never called a phone sex line again. I don’t miss it—I didn’t even enjoy it when it was happening. My urge for human validation remains, though I now have different outlets for it—friendships, writing, stand-up shows, online dating—and it can have healthy results when focused with care. But to learn control, you have to experience losing control first, like I did, that summer in 2001.

—Photo @heylovedc/Flickr

Reprinted from The Good Men Project