The Weirdest Guy I Ever Sort of Dated

Perhaps I am digging myself in a hole by bringing up this guy this early in my blogging career, but I was thinking about him recently (because I think he’s engaged or something. Just goes to show there’s someone for everyone!), and decided it was a story that I wanted to tell. Fret not, fellow awkward-teers! I still have plenty more material.

He was a friend of a friend and he was very cute. He also appeared to be just as awkward and as terrible at flirting as I was, so we hit it off pretty quickly. We used to kick each other and toss out harsh insults because, even though I was 20, expressing my feelings made me just as uncomfortable as it would the average 12-year-old boy. I thought he had a similar strategy for obtaining someone’s love and trust. I later came to learn he was instead the quintessence of an “odd duck” and no better at life than a smelly, old douche.

The first incident of overt weirdness (IOW) was when he asked me to eat breakfast with him one morning before class. We agreed to meet up at 8:45. So, I got there at 8:45 because there is absolutely nothing exciting about me. It was very clear he wasn’t there yet, since there only about 3 other college students who regularly ate breakfast before 10. I got an omelet and I waited.

I am not good at waiting because I automatically assume the worst. When 9:10 ticked by, I began to realize that I hadn’t been asked out for a romantic cafeteria breakfast for 2. I had been led into a trap. I immediately began looking around for a clever place to hide a paintball gun sniper or a bucket of pig’s blood, when I saw him strolling in around 9:15. We had class at 9:30. He looked right at me but didn’t acknowledge me, bought a granola bar, sat down without saying a word, opened the granola bar, took a bite out of it, then looked at my plate and said, “Whoa, big omelet!” (It was a big omelet. I was hungry again 30 minutes later. When am I going to stop this silly writing business and realize competitive eating is my calling?!?!).

I said nothing in response because I was confused. He finished his granola bar, looked at his watch, and said, “Well, time to go. Can we do this again on Thursday?”

…Sure. I could eat alone again on Thursday. In fact, I was looking forward to it!

Thursday rolled around and I trudged into the cafeteria at 8:45 to enjoy solitary meal of silent solitude. I got another omelet and sat down at a small table-for-two. The guy was nowhere in sight. I chewed with my mouth open and got ketchup on my shirt because 8:45 me doesn’t give a shit.

I looked up to assess my surroundings because I would probably choke if I didn’t slow down when I saw him sitting a few tables away with some other guy. We made eye contact and he waved. But what did it mean? Was it a, “Hey, there you are! Come over here!” wave or a, “Oh, God. She sees me. Better be friendly or she’ll eat me next,” wave. I had no way of knowing. So I just sat there and kept staring at him for awhile. Probably muttering all these thoughts aloud with a twitching eye.

He waved again, unfazed, which led me to believe that yes, I was supposed to go over there. I sat down and he said, “I’m so glad you made it. This is Eric.” Eric and I exchanged our hellos, and then he and Eric continued to talk as though I wasn’t there. 9:20 came along and I announced I had to go. He looked up at me with an adorable smile and said, “You have ketchup on your face.”

My natural assumption was that I had been friend zoned. And I wasn’t too broken up about it, to say the least.

One night, my friends and I decided to go to a party in one of the on-campus apartments. So they got all dolled up and I left my day clothes on and followed begrudgingly behind them because I need a barrier between me and the people at all times. The party itself wasn’t that bad as far as parties went. We were dancing and having an okay-enough time when I got a text from the guy that said, “Where are you?” Hmmm…odd. Especially with no context or prompt. Why was he looking for me? Was I the rook is some greater government scheme after all?

I texted him back my exact location and I swear, not 10 seconds later, he burst through the back door with the force of a sassy, drunk giant. He walked straight to me, eyes only focused on me, pulled me into him…

And we started doing about the most awkward dancing that any two already-awkward people in this world could accomplish. It was some uncoordinated combination between traditional salsa, the percolator, and two paraplegics trying to hold each other up. His mouth was open and he was slobbering on me like a horny dog. It was magical.

He came back to my dorm with my roommate and me. She managed to fall asleep despite the fact that he insisted on continuing to dance. This time to obscure 80s Irish music (yes, you read that correctly). He had my wrists in his hands and he was swinging them back and forth with utter fascination, he was looking at me longingly, and so I took that as an opportunity to lean in and kiss him.

It went on for a little bit. He was a surprisingly good kisser. But suddenly, he pushed me away and said, “I like cheek kisses better,” and planted a nice wet one on me. Hey now, what? I mean I had showered that day and my breath probably smelled like peach schnapps. I was a breathing, passably attractive female standing in front of a 20-year-old man and he wanted cheek kisses? IS IT CUTE OR IS IT CREEPY, READERS?!

These weren’t nice little cheek pecks either. He was voraciously kissing my cheek. He was kissing my cheek with passion and fervor. He was making out with my cheek. Now I was starting to get concerned.

“Can I sleep here?” He asked when he finally came up for air.

“Uh…..” (I go over how I feel about sleepovers in Spending the Night: A Tragicomedy).

“I just want to sleep next to you.”

“I mean, okay.”

So we climbed onto my top bunk and laid down. I turned one way thinking he’d want to spoon me or something. He turned the other way and went to sleep.

The next weekend, some friends were visiting my roommate and me from another college. The guy and I had been texting all week and actually ate breakfast alone together and I was getting kind of used to the cheek kissing, I guess, so I asked him to come over and hang out with all of us. He stumbled into my room, perhaps the drunkest I’ve ever seen a person, saw my black friend, and immediately started spurting out some of the most racist things I’ve ever heard. He was an awkward, skinny Catholic racist. He was the boy who couldn’t say a word to me over a granola bar and here he was casually throwing around deeply offensive racial slurs. I had to get him out of there before they all kicked his ass.

He asked me to go back to his room to “read his novella.” This was not a euphemism. This is actually what he wanted to do. Only when we got to his room, he decided he didn’t want me to read it because the story was too nice. So we sat on the floor across from each other in the pitch dark for awhile because he didn’t want to turn the lights on, when he leaned toward me. I thought he was going in for one of his special cheek kisses and braced myself, but instead he whispered in my ear, “Can I tell you a secret about me that nobody else in the entire world knows?”

Well, what are you supposed to say to that other than, “Okay”?

He leaned back and stood up and turned to stare at his wardrobe as though he were a mad scientist staring at his most grand experiment.

“I love to shop,” he said as he bust his wardrobe open with vigor.

And in that wardrobe, lined up and perfectly pressed, were about 50 black V-neck t-shirts. Nothing else.

“I love clothes. I love fashion. I love looking good,” he sighed and sat back down. “So, that’s me.”

I nodded.

We sat there in the dark silence for a bit longer after that and I guess at some point, I fell asleep on his floor. I rushed out the next morning before he woke up, but freaking Eric saw me leaving his room, and then there were rumors for awhile that that guy had finally gotten laid. I didn’t bother to correct them because first of all, I didn’t care. Secondly, who would believe the real story?

There are a few other IOWs from this period of my life when this very strange individual and I were cheek canoodling, including one that involved a pizza party and a suspicious encounter with one of my professors, but this is most certainly the highlight reel. We didn’t talk much after that. Maybe telling me his deep, dark secret took too much out of him. Suffice it to say, my cheeks were grateful.


Confusing Drama with Happiness

People love drama. And rightfully so. Without drama, the world around us is woefully uninteresting. It’s why Grey’s Anatomy is still on the air, why people thirst for Kristin Hannah novels, why when you start hearing about someone else’s problems, you eat it up. I like to think it is because we are prone to empathy and catharsis and not just nosey. Regardless, drama plays a big role in society. Drama exists so girls everywhere can get a nice rise out of rolling their eyes and loudly sighing, “Ugh, I hate drama!” Thus creating drama from their hatred thereof.

I can’t speak for everyone, but in my experience, when it comes to relationship drama, most of the time the men are the main culprits. Here is why: women love when the relationship enters the boring phase. It means they don’t always have to pluck their eyebrows and can eat ice cream right out of the carton and scratch themselves wherever they may itch. When the relationship enters the boring phase, it means you are comfortable, and perhaps going somewhere. Some men can’t handle that kind of predictability. It feels too relationship-y for them. They want the woman who starts yelling at them for a mundane reason and then sobbing from her anger and then proceeds to rip off all of her clothes and take it out on them sexually because she can’t handle her own emotions.

Whenever you hear a guy say, “Dude, she’s crazy,” know that it is the equivalent to our, “Ugh, I hate drama.”

And if you’re wondering why you don’t always have the best of luck with relationships, consider the possibility that you’re just not a psycho. And wait it out for the guy who watches you eat the ice cream with awe and sheer admiration.

I dated a guy awhile ago who was all about the drama. This was a challenge for me because I am not good at creating drama. I approach dramatic or sensitive topics with either humor or general political incorrectness because I am perpetually uncomfortable. But this guy had a very low tolerance for just plain old chilling. Something exciting always needed to be happening, and it was up to me to make it happen.

I couldn’t be confrontational because there was absolutely nothing to be confrontational about. We were usually just watching TV in his basement. What was I supposed to do? Yell about how I didn’t want to watch Entourage and could we please put on TV Land instead?! Flip the table over out of my sheer hatred for Adrian Grenier? It all seemed so pointless.

So, partially as a writing exercise and partially because my relationship depended on it, I started to make up really dark stories about my past.

It was innocent at first. I would talk about being made fun of at school, about always feeling “different” and ostracized for it. Ya know, all that Degrassi crap. He would stare at me with really intense eyes as I would try to get some waterworks going and then we would make out a lot. I liked the making out part. The making out part was the goal. Always.

But it wasn’t enough. I could feel him getting bored with me. I needed an Oscar-worthy twist. I needed to blow minds! I fished for more material. Was I struggling with my sexuality? Nah, not really. Did I have a drug problem? Can’t say that I did. I obviously wasn’t in poverty nor did I have a child. Let me tell you, it is very hard to make up an oppressive story about yourself when you’re a straight, white female from the suburbs.

As I struggled with my search for answers, I reached over to the table and took a sip of his beer.

“I think you have a drinking problem,” he said with narrow, almost expectant eyes.


It is always nice to receive a bit of direction.

This remained a topic of conversation on his part for weeks. He made up elaborate stories about me getting violently drunk and not remembering and would send me information about various programs and self-help books. He would tell the waitstaff at restaurants that he wasn’t going to have a drink because I was overcoming alcoholism. The whole thing was out of control. At this point in my life, you could tally the number of alcoholic beverages I’d had on two hands. Maybe two-and-a-half. But I’m really awkward and he was really cute and I liked making out with him so how in the heck was I supposed to explain that I didn’t actually have a drinking problem?

One night, when I was forced to sit through another episode of Entourage, his father came downstairs for a beer. He had apparently forgotten that I was a recovering alcoholic and offered me one. I shook my head nonchalantly because I, too, forgot that I was a recovering alcoholic. And my boyfriend took that to mean that I was cured.

He wasn’t happy for me. He did not jump for joy. He was immediately bored with me again. He removed his arm from around my shoulders and sighed. “I think you should go.”

“But, I…I,” My lip started quivering from all the pressure, and I’m pretty sure he took it to mean I was going to start crying, so I went with it.

“They used to laugh at me!” Was all I could get out. It was small, but he leaned in closer to me.


I just started shaking my head because I had no idea who.

“Who used to laugh at you?!?!” He took my face in his hands and waited intently.

“Uh…they did!”

“Those bastards!”

And then we made out some more.

That relationship did not last long. My shortest one to date. You can guess why. That dude was crazy!

This is actually a pretty extreme example. It is not normally this intense or exhausting to date anyone.Most people have to use the time at the beginning of a relationship to make themselves seem slightly less crazy. I have to wonder if I’m the only person in history who made myself seem batshit insane just to get a guy. Anyway, I’ve certainly learned my lesson, and can proudly say I am 6 years sober of drama queens.

PS: I’m on Twitter! Follow me @AwkwardPrufrock for as much awkward as one can achieve in 140 characters or less.

My Top 5 Most Awkward “Um…I Don’t Know How to Take That” Moments

Today in America, we celebrate a man who hopped on a ship to find a better way around the tip of Africa. However, he went the wrong way, landed in a strange, rural land amongst a group of locals, and told them he came from a place called Italy in the name of a place called Spain and had now “discovered” them.

Much like those natives probably felt, there have been things said to me in my dating life that have made me scratch my head and go, “Lol what?”

I am not always a tactful person. I think I have made that pretty clear. To the point where I’ve adopted the role of the listener in all of my friendships, and try to keep my words very calculated when the time comes. I have also dated some not-overly-tactful people. And here we have further proof that double negatives don’t work in psychology. –Tact+-Tact=Compliments+Offense=Um…I don’t know how to take that. (Write it down because there will be a short quiz at the conclusion of the post. Also, I’m pretty sure it was on the GRE.)

Here is a listing of the highlight reel.

5. Him: When I first met you, I thought you were the cute and innocent type. But that’s not true, is it?

I get this a lot. People often don’t know what to make of me. I look like I’m 17, sound like I’m 52, and don’t know how to hold a conversation about normal things. The combination just contributes to my awkward. The thing here is that he didn’t elaborate. Did this make me a good witch or a bad witch? What was my type, then? Does this mean I am not cute and guilty? Like a criminal? And not even a cool criminal, but the kind who gets caught and thrown in jail and never attracts the stereotypical attentions of the other criminals because of her not-cuteness but behind her harsh exterior, she just wants to feel loved, dammit? Or was it his way of saying I’m sexy and worldly? I never learned.

4. Him: I feel like you’re the kind of girl people date.

Great so…are you asking me out on a date?

This was before I understood the hook-up culture I was growing up in. I thought that dating was what people did after they had pleasant conversation and exchanged numbers at parties. I didn’t realize being “the kind of girl people date” in college pretty much completely benched you during tonsil hockey season. Also, does anyone else see that this almost contradicts what I was told by number 5? WHO THE HECK AM I, ANYWAY?!?!

3. Him: The first time I saw you, I thought, “I wouldn’t say no.”

Thanks, I guess? I mean I suppose his not ruling me out right away is what allowed us to get to know each other better and date for a bit. But even just an, “I thought you were pretty,” or, “You seemed interesting,” are very nonchalant comments that would have sufficed. I guess it’s good to know I’m not repulsive, but what does a “not no” mean? That as long as I shave my legs, I only kind of resemble a yeti?

To recap, so far we have learned that I am a not-cute, not-innocent dateable distant relative of Sasquatch.

2. Him: I’d say you’re in my top 3.

Out of how many? Top 3 what? If your top 3s are anything like my top 5s, we may have a problem here.

  1. Him: Out of 100? I’d give you an 85.

This actually isn’t a bad score, especially if a 100 is like Grace Kelly or something. But at the time he was my boyfriend of 3 months or so, and I’ve always been a bit of a Hermione Granger type about grades. A B would bring down my Girlfriend Point Average significantly.

As I write all of this, I realize I guess I go for the candid type.

Also, I think my life’s goal is for Columbus Day to be replaced with Awkward Day, when everyone can have a day off from work in the name of all that is awkward. Because that’s what America is really about.

All of the Reasons I’ll Never Ask You Out

  1. You might say no.
  2. You might say yes, and I’ll just stare at you in shock and then you’ll change your mind.
  3. You might say yes and then yell, “PSYCH!”
  4. You might say yes but then we never make a definitive plan and the date never actually happens and every time I see you, it’s awkward.
  5. You might say yes and then I suggest a sushi place, but it turns out you’re allergic to sushi and you call me insensitive.
  6. You might say yes and then cancel.
  7. You might say yes and then not show up.
  8. You might say yes and then show up with another woman, and I find myself entangled in a weird sex arrangement.
  9. You might say yes and then get into a minor car accident on the way to the date and then resent me.
  10. You might say yes and then we go somewhere candlelit and my hair catches fire and I have to go to the hospital.
  11. You might say yes and then we go someplace for hot coffee and I spill it in my lap and have to go to the hospital.
  12. You might say yes and then we go out for dinner and you choke on your food and then you have to go to the hospital.
  13. You might say yes and then I will catch a stomach virus but I won’t want to cancel and we’ll go somewhere and I’ll throw up on you.
  14. You might say yes and then the first date goes well, but the second date is sub par and you lose interest.
  15. You might say yes and then I realize I don’t like you that much and I’ve wasted a perfectly good Saturday.
  16. You might say yes and then we have a good time, so I invite you back to my place and you rob me.
  17. You might say yes and all goes well and then you take me to an alley to meet your drug dealer.
  18. You might say yes and we go to a museum and are mistaken for famous art thieves and end up in jail.
  19. You might say yes and then we date for a few months and then you break up with me and I’m sad.
  20. You might say yes and then we date for a few months and it turns out you’re a serial killer.
  21. You might say yes and then we date for a few months and fall madly in love and then you become terminally ill.
  22. You might say yes and then we fall madly in love, but your mother hates me and you have to choose between us.
  23. You might say yes and then we fall madly in love and I find out you’ve been married all along.
  24. You might say yes and then we fall madly in love and then you propose to me and yell, “PSYCH!” and run away and I never see you again.
  25. You might say yes and then we fall madly in love and decide to get married and it’s expensive.
  26. You might say yes and then we get to our wedding day and you suddenly realize you’re gay and run out of the venue and hop on the back of some dude’s motorcycle.
  27. You might say yes and then we get to our wedding day and Scarlet Johannson suddenly gets up and professes her love for you and how can I compete with that?
  28. You might say yes and then we get to our wedding day and Ryan Gosling suddenly gets up and professes his love for me and I have to choose.
  29. You might say yes and then we get married and then you get kidnapped on our honeymoon.
  30. You might say yes and then we get married and then we grow to hate each other and get divorced.
  31. You might say yes and then we get married and I find out I’m your second family.
  32. You might say yes and then we get married and have children and never have sex again.
  33. You might say yes and then we get married and our children are horrible people.
  34. You might say yes and then we get married and win the lottery and the money corrupts us and ruins our relationship.
  35. You might say yes and then we get married and I find our your job was never technically legal.
  36. You might say yes.

So it is pretty safe to say, gentle-eyed creature across the crowded room, that if you believe there is any future for us, please, in the name of all that is divine, make the first move. Any hope we have depends on it.