Sexting Etiquette 101

Socially awkward and (digitally) dyslexic, I clearly don’t know much on the topic of sexting. But, if there’s one thing that a previous dating encounter has taught me is that one might actually need to have sex with the other person before it becomes appropriate to snapchat dick pics and initiate other forms of mobile misconduct.

I met Corey* (I promise, no resemblance) at a party over the summer and was instantly attracted to him. The type that walks past you, and you say to your friends, “did you just see that guy?” Normally, I would retreat to the corner and avoid eye contact, but fortunately a friend of mine forced me into a blackout state and encouraged me to buy him tequila shots.   We spent the entire night together, and he ended up getting me home “safely” around 2am, and a drunken make-out pursued, nothing more. Following his exit, I received a text (while eating a leftover sub) about “the sexiest thing he’s seen in a long time.” What? Uh, me? (meatball still in mouth.)


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Official Date 1 (Thursday): He was such a gentleman. Conversation and flirtation were on par. He touched my knee. The sexual tension escalated. At the end, he walked me to my door and we made out. He politely texted me that night following our date.

Date 2 (Thursday) was much more drunken than the first. The sexual chemistry was magical. He walked me home and we aggressively made out. My bra ended up on the sidewalk while an onlooker yelled, “get a room!” I ended up going upstairs (alone) to partake in his further aggressive sexts about “his boner coming through his pants.”

That Sunday evening, on my way back from Maine, I received numerous texts from him begging me to come to his place when I got home. The conversation soon escalated into what he wanted to do to me in a dark train car. I wasn’t sure if this was normal or not, considering I wasn’t even confident if his penis was larger than a crayon. But quite frankly, I didn’t care. I hadn’t experienced this much sexual tension since college, and was relishing every moment of the chase and sexual build that I had only once had the will power to control when I was a sad 20-year-old virgin.

Date 3 (Thursday) was two stops (drinks and food), which actually seemed like an eternity when all I wanted to do was finally take this digital foreplay into action. Upon return to the scene of the “sidewalk bra,” we walked up to my apartment, only to discover my roommate home on the couch. Not really the ideal setting for crazy, christening sex in my (non) soundproof converted bedroom. He decided to go home, but that we would hang out on Sunday when he got back from a Bachelor party.

Sunday evening: I distinctly remember texting Em on the cab ride over, “heading up to Corey’s to finally have the most anticipated sex of the century.” When I arrived, we put on some lame Jamie Fox movie as background, and immediately started making out. The progression followed at a natural pace, including a last minute condom (and Twix bar) run to CVS. When he got back, he FINALLY put it in…

20 seconds and it was over.

I can’t even begin to describe what was running through my head. Are you seriously done? Is this going to be a regular thing? Also, when is it okay to eat that Twix bar? So many thoughts.  He never acknowledged, so we continued to “watch” the movie and eventually passed out.

The next day I re-evaluated. Did he think that was normal? No, he had to have been embarrassed. Especially after all of that sexual initiation on his part. Regardless, it was more than worth figuring out if this was a one-time thing or a regular occurrence. Plus, I think I may have actually started to like him.

Over a week later, we ended up meeting up for drinks to give it another shot. It was funny actually, as on this date, the sexual undertone had been 100% removed from the table (and replaced with a nice cheese plate). Ironic, as shouldn’t post-sex relations usually enhance the mood? Clearly 20 seconds is a hard act to follow.  Regardless, we still had a really good time, and went back to his place after. I was anxious, eager, excited, among many other feelings, for the second time around.

It was like night and day. The positions, the rhythm, the “energy,” the timing (yes, it was long!). Down to a science.  I was felt a wave of relief come across my body, and actually started thinking… hey, maybe this could actually be something?

…And then we turned on the lights.

Blood. Everywhere.

I was mortified. Period. (Yes, pun intended.)

And needless to say, that was the end of that. I didn’t really hear from him after. No call. No follow up sext…”hey, can’t wait to massacre you again tonight.” But I did get a dry cleaning bill in the mail a couple weeks later…

Kidding! But seriously, all kidding aside, what’s the moral of this here sad story? (because I feel like we always need to leave one.)

SAFE SEXT. A good rule of thumb…don’t do or say anything via phone, which you have not yet performed (or seen) in real life.



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YOLO For a Man-Child? NO, YO!

ImageI buckled my seatbelt, laid back and prepared to slip into a deep ambien sleep for an easy 5-hour flight across the Atlantic Ocean.

But within about 3 minutes, I had broken into a cold sweat and found my face softly enveloped in the barf bag from my seat pocket. Is this really happening? As the older gentleman next to me looked on with confused concern, I quietly and neatly barfed, wiped my face and reached for the flight attendant assistance button.

The ambien was inhibiting my ability to analyze why I vommed – I’m not afraid of flying and get no motion sickness- was there bad Gorgonzola in my Cosi Signature Salad? Only looking back am I realizing that it was from anxiety about what I was about to do.

Back up about 12 hours. “You shouldn’t go,” my mom declared. “You can’t fly to London for any man – boy? – who’s going to let you take a bus.” Desperate for some romance amidst the Washington DC dating scene, which is infiltrated with preppy douchemonkeys whose egos far outsize their sexual prowess, I was taking 2 days off for a “romantic European getaway” with a 25 year old English skipper I spent 3 reckless nights with on The Yacht Week over New Years. We had talked for 3 months every day – 3 months! The average guy I’ve dated in the US avoids phone calls like zombies with AIDS – shouldn’t I at least see if there’s something there? So I used my precious United and Hyatt points from my extensive work travel and planned a spontaneous long weekend in London. YOLO, right? Wrong. Girlfriend, he was calling you every day cause he aint got no JOB.

So back to my mom. That’s when he had dropped the first bomb, the day before my arrival. “Can you come to Cambridge for the first night? It will be fun!” Fun? You live above your parents’ garage, it’s a 2 hour bus ride from Heathrow, and I know you’re only suggesting it because you can’t afford the city for an extra day. But *of course* that’s not what I said: “Sure! Would love to meet your friends and I’ve always wanted to check out Cambridge! Have you at least told your parents I’m staying?” “No worries…they won’t even notice, we’ll be out and about.” All the times my mom warned me against dating younger suddenly made sense in a moment of zen.

So there I was, regretting this whole thing, puking for my first time on a plane.

I’m a fan of efficiency, so let me take you on a fast forward journey through my England adventure: the bus breaks down it takes four hours to get to Cambridge I’m exhausted we do a punting tour and he haggles the owners for 45 minutes to let us go for free we split the check at lunch we club that night I get my iPhone stolen he makes me wait in the freezing cold to smoke even though he knows it makes me nauseous he can’t have an orgasm that night the next day he leaves me waiting alone for an hour in the cabana while he packs in his parents house we almost miss the train it’s raining in London and so cold I’m numb we wait in line for an hour at the club his friends are at by the time we get to the front of the line they leave he proceeds to spend the last of his money on shots the next day I have to buy us lunch oh wait I have to buy us dinner too I find he actually has a problem coming about 30% of the time throughout the weekend the last day I buy us sandwiches he stops at a convenient store and buys *cigarettes* after you let me buy you a sando and bought cigarettes? he’s so embarrassed he insists on showing me his bank account balance at an ATM it’s negative i now understand addiction.

Moral of the story: Trust your gut.

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There’s Cheap… and Then There’s Bring-a-Flask to the Bar Cheap

yhst-62307527738446_2256_6922003Whenever some guy hits on me in a bar, I just want to lie down and take a nap.

Parties are different. At parties, there is a sense of community and one has reason to believe the chances of a serial killer being among the group are below 10 percent (at least.)

So when a Heath Ledger look-alike approached me at a friend’s party in Bushwick, I didn’t immediately have the urge to fall asleep. In fact, I don’t even think I yawned.

We flirted, played flip cup and made out in a dark room. It was fun. The following week, we had some solid texting (he had good texting skills, which is very important in this day and age.)

He picked a good spot on the Lower East Side for drinks. He looked good. Everything was good. It was destined for disaster.

I had arrived earlier without knowing he was already there so we both had drinks in our hands when we sat down together. The conversation was fun and flowed easily. Unfortunately, the drinks did not.

The waitress approached us and asked us if we’d like another. I ordered a beer, but he decided to hold off on another whiskey — at least, that’s what I thought.

The server wasn’t two feet away when he reached into his pocket, took out a flask and poured its contents into his empty bar class. I was shocked. I thought there would at least be some kind of joke (embarrassment? humility?), but no.

“I’m in law school,” he said, as if that explanation were the answer to all my life’s ailments.

We went to another bar.

Why did I continue hanging out with him, you ask?

The truth is, I had double-booked and was meeting another guy afterwards. Don’t judge me: I live in New York and I’ve been single for two and a half years.

I decided I was going to need a stronger drink for this one. I ordered a Stoli Blueberry and soda, then turned to Mr. Stingy to let him order. But he wasn’t looking at the bartender — he was staring at me aghast, as if I had just ordered Foie Gras with his grad school tuition loan money.

“I’ll get this one,” I offered, just to get that awful look off his face.

It was as if I had saved his life. He beamed a huge smile my way and said to the bartender, “She’s the best.”

It was single-handedly the most tragic compliment I’d received in my entire life.

Finally, I went to meet up with the other guy, who actually had a wallet filled with contents other than some old Bazooka Joe wrappers and change.

But before I could leave, Mr. Stingy demanded a goodnight kiss. He even suggested we go back to his place!

The next day, I awoke to a text from him asking when we could hang out again.

My response was honest, if a bit harsh.

I replied, “Perhaps if you put away a dollar a day for the next three months, Christmas could work.”

“Great!” was his response.


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Dating Diagnosis: Arrogant Attachment Theory

From the time we are permitted to read Cosmopolitan, the social expectations of sex, and its cruel aftermath, are ingrained in our pre-menstrual psyches.  As a general rule, young girls are strongly advised not to sleep with a guy the first time they meet him.  In the rare case that such a “devious” act happens, paranoia instantaneously sinks in…

“I wonder if I’ll even get a sympathy text tomorrow?”

“Should I have at least pretended to “look” for a condom in my roommate’s room?” 

“I’m really regretting not shaving my happy trail.”

As his perception of our “devious” actions is out of our control, we become consumed by what’s he thinking.  So this poses the question of today’s post – what is he thinking when you don’t sleep with him?

I like to refer to this “Dating Diagnosis” as Arrogant Attachment.  Sparked by a recent hookup experience that has actually happened to me twice, I will consider this occurrence a pattern for the time being.  But if it happens a third time, I’m labeling it a theory.

Last Saturday, I went back to my apartment with Dominic* (who I have met briefly once before).  We fooled around for a while and despite his aggressive attempts, I put up a tough match of “dick dodge-ball.”   The morning was filled with further attempts, flirtation, and him insinuating future plans. 12:32pm.  He meets my roommate upon exiting and she jokingly asks him, “Did Molly fulfill your needs last night?”

His response, “No… I think she’s trying to date me.”

Stop everything at once. Date you? Excuse me.  Joking or not, either way you’re not funny.  I don’t know you.  Remind me, why do I want to start a relationship with you?  But alas, something in the male brain now seems to equate “no sex” with wanting a relationship (and wanting one right away — with a complete stranger).

blog post 3So where did this idea come from? Is this male notion reinforced by society’s consistent need to tell us who we are based on our bedroom behavior?  “Slutty” if we put out, “desperately seeking relationship,” if we decide not to have sex with a stranger.  I say no to sex, and suddenly I’m a clingy, husband-hunter?  The Ginnifer Goodwin character in “He’s Just Not that Into You” is an extreme example, but you know the type.

I would like to set the record straight for all of you men.  For those of us “normal” girls who greatly fear coming across as that desperate/over-bearing type, please leave the post sex-judgment at the bedroom door.   And please do not assume that we are attached to you, you arrogant pricks.  Maybe, we just weren’t that into you.

*Name was changed to protect the privacy of the prick

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Dating Diagnosis: Will Hunting Complex

As a rule of thumb, it’s safe to say that as a single girl in Manhattan, it’s a rarity to have a “good” first date.  So when one comes along that can actually be classified as “great,” it often leaves us with exceedingly high expectations.

By definition, I am referring to a “first” as anything from a drunken hookup to a formal introductory dinner (in this case, I’m referring to the first instance).  So when we leave these “great firsts” – few and far between – what comes next is what I like to refer to as the classic “Will Hunting” complex.

Sadly, no, this hookup partner does not look like Matt Damon circa 1999.  It’s a reference to his character’s first date with Minnie Driver, where they engage in witty banter, both appealing to the other with the perfect mix humor and intellectual stimulation.  Hunting leaves the night thinking “this girl is perfect,” really reflecting his own fear that she perceived him in the same light.  Obviously, the next date can’t go as seamlessly. (And no, I shockingly never studied film).

Cut to February 2012.  Me.  At a neon rave.  Clearly on the prowl, I strike up a conversation with a random guy I’ve never met before – and 10 hours later we’ve watched the sunrise on his roof, made spaghetti, listened to music, played a sexual version of “ring toss,” and eventually, we decided to sleep together.

Not caring at all if I was going to be interested in this guy, I was myself.  Relaxed.  Not over-thinking.  And I ended up having one of the most memorable nights.  After spending 10 hours straight with this complete stranger, I could tell he felt the same way.

After two weeks of texting nonstop, we finally met up again at another bar.  This time, however, I was consumed by these expectations.  I felt I had to act a certain way, which had me over-thinking.  My jokes weren’t as funny.  The conversation wasn’t as “on.”  And I left his apartment that morning knowing I would never hear from him again.  And what do you think happened? Self-fulfilling prophecy strikes again.  Needless to say, this situation has happened to me more than once.

So, why is it that we have these great firsts with guys and never hear from them the second time around?

Is it us? Do we, as women, over-think our actions that much, causing us to self-sabotage?

Or do men, the simple creatures that they are, lose their “fleeting” interest that quickly?  And why is the decision in their court?

I don’t really know why this happens, but if anything, I’m now more inclined to the bad first date.  Heck, next time, I may even decide to spill a beer on him.

After all, many great firsts have started as “bad” dates. I’ll leave you with this.

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The Inevitable Next Morning Brunch Date Suggestion

I woke up last Sunday in a the bed of a guy with whom I have gone on about four dates. While it’s common for some people to get brunch the next morning, this is something I do NOT do. Why? Because why would I go to breakfast with the person I’ve just hooked up with when I can go to brunch with my friends and talk about the person. It’s a no-brainer. Also I like to eat a lot and feel weird doing this in front of I guy I don’t know well.

So, I usually make up an excuse if and when I’m asked to brunch the next morning, which usually sounds something like, “Oh, I’m not really hungry” against the background of audible stomach growls, or, “I would, but I’m have other plans which I can’t seem to recall at this moment…”

But sometimes they are extra-persistent. Over the summer, I used the excuse that I was already getting brunch with some friends, but he was at my place so I couldn’t just leave and grab a bacon egg and cheese at the bodega on the corner. He lingered. He kept inquiring about the nature of the plans. He asked me the inane question, “So, do you like brunch?” Yes, I like brunch. Name me one living soul in New York who “doesn’t like” brunch. If you want me to ever go to brunch with you one day, you better think of a better opener than that, dude.

Anyhow, my friend Molly happened to be in a similar predicament with the guy’s roommate, but she had already ordered food with him hours prior and eaten it naked in bed (such is her comfortable relationship among men and food). Finally, we fashioned a story about meeting our friend who was visiting for brunch so they really HAD to leave. Like now.

It was 1:00 p.m. by the time I got to Molly’s and I was starving. It was unpleasant. I had a fun night with the guy before, but his brunch inquisition and subsequent lingering the next morning put a slightly bad taste in my mouth. In short, we did not see each other again for a little while.

So, that is one example of the inevitable awkward brunch conundrum. But I digress. Back to last Sunday.

I’m just going to get right into it because there’s no easy segue from the last, which is a pretty typical incident, I think.

He asks me to brunch…. WITH HIS GIRLFRIENDS.

He asks me to go out to breakfast with three friends of his who are female whom I have never met before.

I’m not making this up.

Here are some of my many reactions, which I openly voiced (it’s a casual thing, so):

“Why would I ever want to get brunch with your girlfriends?”

“I cannot think of something I want to do less in life.”

“I can’t believe you asked me to do that.”

“I’m actually offended.”


Maybe I’m overreacting, but come on. When a relationship is new you keep the brunch to one-on-one. If you have some mutual friends, great. If the friends are guys, OK, fine. But just him and his female friends? No. Just… no.

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“We blog it like it is.”

A blog committed to providing commentary on everyday life from the eyes of two 20-something social critics.  Like many of you New Yorkers that have these crazy ideas and funny encounters (but don’t have the time to put them down on “paper”) well, here’s two people that do.  When we’re not busy saving lives and doing other important things (“Desperate Housewives” marathons), we blog it… like it is.

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