The Casualties of Staying Casual

Is there anyone out there who is good at keeping it casual? I’m not talking about one-night stands here. I’m talking about having someone consistently in your life whom you enjoy hanging out with, whom you care about, and with whom you occasionally engage in the sexy times. A “fuck buddy,” if you will: a person who is able to reap all the benefits of being your boyfriend/girlfriend without the actual label or “responsibilities” (the responsibilities usually having to do with the only getting to sleep with one person part). If you have an example of any time in history in which this kind of relationship didn’t end in a giant monsoon of hurt feelings and confusion, I want to hear from you, because I want to be able to understand it.

I’m a serial monogamist. I never feel a need to stray from the person I am with at that time. How do you keep your stories straight? How do you keep them all interested? How can you spend all your time with one person and not have feelings about their feelings? I’m a feelings machine. When I totaled my car two years ago, I cried for days because I thought it was so noble of the car to sacrifice itself for me. I get flushed with nostalgia whenever I check out of a hotel room. So to ask me to let you be in my life but to keep my feelings in check the entire time is a lot. However, because I am slightly masochistic, this has not stopped me from trying it out!

I was once entangled in a so-called casual affair for about a year. A year. And here we have the first complication of keeping it casual: how do you end something that didn’t start? That isn’t real? You can try to let it fizzle, but if you genuinely like the person and they’ve been in your life for a while, the fizzling becomes nearly impossible. Also we as humans are naturally attracted to routine. And so both of you get so used to your arrangement that you don’t realize at least one of you is miserable.

It starts off all well and good–pretty typically, actually. You make time for one another. Your heart still skips a beat and you can’t help but smile when you see you got a text. You feel yourselves lost in an expanding bubble of silly puppy love and it-just-doesn’t-get-any-better-than-thisitis. But then you get the 4th or 5th date and you start having questions. It looks like a relationship, it feels like a relationship, it smells like a relationship…but is it, though?

The thing is it’s going well. You’re happy. So why ruin it with the R word, with the talk, when things are fine just the way they are? Besides, how differently could he be feeling? You’ll get your answers eventually. Probably soon.

And then one day, a few dates later, when you walk into the bar to find him chatting up another girl, you get a pat on the head and a, “I just love how cool you are about this.”


One of the many problems here is that you are still slightly flattered by this comment. Like, “Yeah, that’s right. I can be cool. I’m a cool girl. I’m cool like dat. I’m not upset or hurt or angry or anything. Chill like dill, mofo.” The thing is now your bubble is popped. And so there is the first casualty of your casual relationship. Your bubble is popped and replaced by the bit of rage that’s starting to flow through you like mercury in a thermometer.

But you still continue in spite of your rage because there’s always that possibility, that glimmer of hope, that this particular guy, in a vast ocean of all the guys out there who would date you, will fall in love with you and have babies with you, because, to quote the most almighty quotable being, Albus Dumbledore, “Humans have a knack for choosing precisely the things that are worst for them.”

The guy I was with was incredible at the whole casual thing. Made an art form out of it, really: long gaps between messages, being non-committal about hanging out, keeping me very separate from the rest of his life. However, as I mentioned before, I am a serial monogamist, so perhaps the biggest problem was my inability to be casual back. How does one casually express that I just want to make you muffins and maybe cuddle a bit? So one day, I decided to change that. And don’t worry guys, I won’t suspend you in mystery: it was a terrible idea.

We decided we were going to do a local trivia night. A typical activity for us. I love a good, ol’-fashioned trivia night. Useless knowledge is my favorite (and perhaps only) kind of knowledge. However, why play with a team of just two when you can go up to four? Do you see where I’m going here? Do you see the disaster that is about to unfold?

While I can’t say that it happened purposely, we both kind of brought other dates.

Yup. The old your date brought another date awkward moment.

I can’t say I meant for the friend I brought to be a date per se. It’s just that I knew he was bringing a female friend of his and he was being so very laid-back about the whole thing, and I wanted to be the cool girl, and the cool girl probably has lots of good-looking male friends who she just chills with, the same way she just chills with her concubine. I can’t say I meant for it to turn into a blood bath. Truly at first, I was trying so very hard to be the cool girl. So naturally, as an awkward person trying to be cool, I was failing miserably, and in turn breeding more awkward. It was still civil enough…but the thing is about two rounds into trivia, she started sensually rubbing her foot on his leg… and she challenged me on the theme song to Murder, She Wrote.

I’m not normally the jealous type, and the truth is I had no right to be, in this situation. But we’d had several bottles of wine and you do not contradict drunk Jillian on classic TV trivia. You just don’t.

And that’s the problem with casual arrangements. Not only was I having feelings, they were feelings I wasn’t allowed to be having, which means they had spent the last couple of months fermenting inside me and getting ready to explode. It was one of the uglier nights of my life. I was slurring out insults and making drama, I was stumbling around and not making sense, she was calling me sloppy, he was calling me crazy, my “date” thought he’d help the situation by trying to hit on the other girl. It was the least and yet most myself I had felt the entire time we had been together. The good news we were on Long Island, so the whole debacle looked pretty normal to passersby.

So the lesson here is, if there is one, don’t bring a date to your date. You will end up drunk crying on your bedroom floor at 2am, texting your friends and asking them if you’ll ever be worthy. Of course you’re worthy, ya whackjob. Pull yourself together.

And I kept seeing him. Told you I’m a masochist.

There were times when I’d try to pull away, when I would try to end things, moments like when guys would ask me out or if I had a boyfriend and I never knew what to say. And he would say something sweet that would suck me right back in. Then there were times when he’d start to get attached, and he’d say it was over, only to call me again a week later. We both had our fair share of times when we thought it would be healthiest to stop, but we were inexorably drawn to one another. He’d tell me he really cared about me, but that he couldn’t be in a relationship. I’d say I understood. And I did. That didn’t make it the right thing for either one of us.

Then the day before he left for a month-long business trip, he told me he loved me. I told him I loved him, too. And that meant something to me. Those aren’t words I believe should be thrown around like a Frisbee. He said he’d talk to me when he got back. And I naively thought this was a game-changer. But I’d had no confirmation. Always get it in writing, ladies.

I guess it was when I saw the Facebook pictures of him kissing another girl was when I finally got my head on straight. I confronted him about it, very calmly. And he responded, very calmly, reminding me that we weren’t in a relationship, that he had told me repeatedly that he had never wanted anything serious, and he was right. And that’s when I felt my stomach fall out of my ass like a sea cucumber (that’s right, sea cucumbers can digest major organs! Told you I’m good for the fun facts). This moment was when I was finally able to sever the ties between my physical and emotional feelings for this man.

The whole shellacking turned me off to dating and men for a good amount of time after that. Until I realized it is just stupid to accept anything less thn what makes you feel happy and right in that time in your life. But I feel like crazy dating choices are a rite of passage for all of us…my quota is just, like, triple that of the average person.


My Top 5 Most Awkward Stranger Flirtations

Hi there, everyone! To start off, this past Wednesday was my 25th birthday. Therefore, we celebrate a prestigious milestone: a ¼ century of awkward. Here’s to ¾ more (because I live in the hopes that longevity and awkwardness are directly correlated).

Today on J. Awkward Prufrock, we will closely examine (and justify) my fear of strangers, particularly those of the randy male variety.

I’ve always been shy, but after a year of working in New York City, now I’m just downright vigilant. I thought I had no people skills. Who on earth taught some of these men how to woo? And then you have to wonder if it’s a trial and error sort of thing or if this stuff really has worked for them before…

Presenting my top 5 most awkward stranger flirtations. Enjoy. And remember, CONSTANT VIGILANCE!

5. Walking behind man in parking lot on my way to the bank. Man sharply turns around and points at me.

Him: You followin’ me, pretty girl?!

You have to understand that he said this so loudly and looked so angry, that despite the fact that he made it clear it was just a line, I was absolutely terrified. My eyes bugged out of my head and I think I shook a little bit. In his defense, he did follow up with, “I’m sorry. I was joking. I’m a joker, ya know? I make jokes.” Well, that made all the difference. Because when you’re sitting in a circle at a slumber party with your girlfriends, you always describe your ideal guy as “a real joker.”

4. Dozing off on the LIRR, when a conductor nudges me awake so he can punch my ticket. I open my eyes to see a (tragically) cute man staring at me from the seat in front of me.

Him: It’s too bad he woke you up. You looked so peaceful. I liked watching you.

You know what’s the worst part about train travel? There is nowhere to RUN!

3. Him: I like girls. Can I buy you a drink?

I guess he decided to add a juvenile charm to the age-old classic, “Can I buy you a drink?” Was that his tactic? Maybe? I just don’t understand why he led with “I like girls.” By posing the question, he only gave me more questions. Maybe because he was wearing a sweater vest? It is no matter, as this was long before I understood how things work, and could not comprehend why he would offer to buy me a drink when I had a full one in my hand, and I told him that, and I swear I’ve never seen anyone turn and walk away so quickly.

2. Man with teardrop tattoo grabs my shoulder and stares into my eyes intensely.

Him: I’d like to talk to you about anarchy.

Me: What?

Him: The only way we can escape is to fight it. Power. Greed. Corruption. Violence. Join my cause.

He may have not even been hitting on me. I just thought it was fuckin’ weird.

And nothing will ever top this one.

1.Walking through Times Square, make awkward eye contact with guy as he walks by, so I give him a small smile. Suddenly I hear the sound of a bag dropping and feel a pair of arms around me. He dips me. His breath is horrible.

Him (with heavy Russian accent): Hello, I find you beautiful. My name is Constantine. Meet me tonight and I will make love to you.

The thing about Constantine is that he clearly had sales training. He didn’t give me a choice about the whole making love thing. He was demanding it. I don’t think I even said a word the whole time. He was pushing his phone into my hands and before I knew it, I was punching numbers in (granted, they were not the correct numbers). I still walk through Times Square with one eye over my shoulder.

Text Anxiety

Texting someone new is an emotionally agonizing experience. Usually when you just start texting someone, you’ve only met them once or twice, which means the foundation of your relationship thus far is probably, “You seem nice, and I’d probably bang you before I’d bang the people surrounding you.” Thus the entirety of your future relationship lies within the rectangle in your purse. The texting will prove if you are verbal matches, if you can repartee, banter, if you are compatible spellers or grammartists (not a word, but dammit it should be!). Your texts have all the power to make or break this thing, and your strategy is imperative, like a game of chess. And if that isn’t pressure, I don’t know what is.

It all starts off with the exchange (cue ominous music).

I have never asked a guy for his phone number because I never want the ball to be in my court. I was tricked once by a guy who was developing a texting app on which you could send people doodles, so he asked me to help him test the app and send him a doodle. He was unbelievably gorgeous and charming, so naturally I acquiesced. What did I send him? A poodle eating oodles of noodles. That was the best I could do. I did not send a heart or a smiley face or something flirty. I sent things that rhyme with doodle. Because I am a hopeless case. But I digress.

The exchange. So, he moves first. You are going to give him your phone number. Your real phone number. Not 10 random digits that come into your head, not your very large brother’s phone number. Your actual phone number. He should pat himself on the back for that one as it is. And then you play the waiting game.

There are some devious bastards out there who send a text right away with just their name. They make you think they are braver than you by asking for your phone number, indicating that they ain’t afraid of starting this thing goshdarnit, and then they do a cheeky flip-flop on you, leaving you nothing to work with, and the two of you are stuck in a text stalemate. Nobody wins in a text stalemate.

Then there are the guys who abide by the three day rule, because they get some kind of sick joy out of knowing that you are going absolutely crazy wondering why on earth they haven’t texted you. There are also the guys who never text you because they just like collecting numbers from people, knowing that they can text them if they feel like, because they’re big shots. It’s very easy to have a lot of friends when you don’t try to talk to any of them. Stay away from both these types. They are not worth your time (note that this is me talking to me here).

The guy who texts you as soon as he gets home might be worth a word or two, but oh dear Lord, what should those words be?

You hear your phone ping and naturally you grab it right away (I actually do not have a text tone or vibrate for this very purpose. This sort of anticipation would literally kill me). You see the unrecognizable number displayed proudly across the screen, and you open the message app to reveal: “Hey, it’s Brian. How r u?”

Oh dear, indeed. How am I? Victorious, that’s how I am. So victorious that I am going to look past his use of text abbreviations, you think as you do a little happy, jumpy shimmy. (It’s not that you’re against abbreviations, per se, it’s just that with the invention of touch screens, typing out whole words is so easy and it makes the sentences look so complete and beautifully English and it makes you, Brian, look oh so smart and careful…but you have nice pecs so…) But rather, how does Brian want me to be? Sexy? Is that a state of being one normally associates with oneself? “Hey Brian, I’m sexy.” No, that’s not right. How am I really, though? Tired? Yeah, I’m a little tired. Should I tell him that? That I am tired and exasperated by dispassionate jaywalkers? Is that hot? Are people for or against jaywalking these days? I can never keep up.

You ponder your answer for 17 minutes before you settle on something, but hey, you don’t want to appear too eager anyway.

“Hey Brian. I’m good. How are you?” Yes, that’s good. Keep it generic for now. Jaywalking opinions are solidly third date conversation. And you’ve asked him a question, you brilliant minx, you. Now he has to answer you. It would be rude text etiquette not to.

His response comes in a mere two minutes later. Brian knows Brian, Brian knows how Brian is. Sigh.

“I’m good. Last night was fun, right?”

Now, you’re feeling a bit manipulated. I mean, you did have fun, but he is sort of telling you that you had fun and also asserting that he is right all the time. Brian probably didn’t put that much thought into his semantics, but it is all in the subtext. Do you really want to be with a manipulator? What else will Brian insist is right? You’re pro puppy killing, right? Dessert is awful, right?

But…the pecs!

“Yes (or should I put, “Yeah”? Is “yeah” a bit more aggressive? A bit more laid-back, yet powerful? “Yes” might be read as, “Yes, sir,” and then that may put me in the weak spot. Ooh ooh ooh! I got it!).” Accordingly, you delete “yes” and put, “Yup. Very fun.” It wasn’t just fun, Brian, it was very fun. You don’t know everything.

But…what else? “Very fun” is not a conversation starter. It may even make it look like you are avoiding conversation. And you aren’t. Not yet.

“Yup. Very fun. Would’ve been more fun if there’d been a clown.” God, you’re smooth.




What the fuck are you supposed to do with that one?

First of all, Brian, I know you didn’t laugh out loud because it wasn’t that good of a joke, but you probably would have laughed out loud if you had made it, you cocky son of a bitch. I opened an infinite number of conversational pathways by introducing a clown character, and you write it off with a Lol. Is this really how you want us to end, Brian? I will not give you that power. You will not have the last word. You will not have the last Lol.

 Alright, you, what’s your next move?

You could ask him what he’s up to. No, you can’t, because then it might make it seem like you’re trying to hang out, and you just saw him 12 hours ago. You could expand on the clown thing, but you’d probably only be met with another Lol. What you need to do is give him something he has to engage in, something he cannot ignore. Something interesting that reveals something about you, just so he has an idea of the mess he’s getting into.

You change the channel and find that Lord of the Rings is on and that it will be followed by The Shawshank Redemption. Man is it a great day to be hungover. Ooh, that’s it! Movies! I will ask him about movies.

“Have you ever seen Lord of the Rings?” This is excellent. From here you can talk about characters, which installment is his favorite, if he read the books, how much Quenyan Elvish he knows. Oh, the possibilities!

And two hours later, you have been met with silence.

What did it mean? Was he not a fan of Peter Jackson’s interpretations? Was he out at another bar getting another girl’s number, telling her about the crazy girl from last night who had a thing for clowns? Was he dead? If he was dead, you’d have no way of knowing. The most anyone in his life would know about you is you were this chick he was trying to bang, and even if his family and friends looked through his phone, unless you were clearly labeled as The Chick I am Trying to Bang, they’d have no way of knowing the brief role you played in his life, and even then they’d still have to care enough to send along a, “Hey, just so you know, Brian’s dead” text, and you’d wander through the rest of your life occasionally wondering what happened to that Brian guy and if he did like Lord of the Rings and how he felt about jaywalking.

You try to distract yourself with the glorious movie marathon unfolding in front of you. You put on sweatpants, you reheat the pizza, and you’re just starting to think life doesn’t get any better than this anyway and Screw You, Brian, when your almighty phone pings once more.

“Lol no.”

Yeah, this isn’t gonna work. Check and no mate for you, Brian.

I have since thrown caution to the wind when it comes to texting/talking to a guy and tend to go full throttle with my weirdness and candor. I am luckily blessed with a boyfriend whom I can text at any time of day about a variety of subjects, from ram gagging to building forts out of cake to raps about the dangers of drugs, and he will listen to me rant about jaywalkers (if there is a car coming, you run! Run, you whackjob! That car is so much bigger than you). But boy, have I been there. And if you have never experienced text anxiety, I want to know who built you.