On Sleeping With Sad Boys


“You wanna get out of here?” The invitation was firm but casual which is probably why I followed him out of the bar and into the back of a cab, drunkenly making out in the backseat on the way to his place. We were interrupted several times by the driver asking for directions, though I’m sure he didn’t need them — no cabbie wants to deal with a drunk couple trying to get freaky in their freshly cleaned back seat.

Back at his place, we blew through three condoms while he used the Lord’s name in vain every other word. The details are fuzzy — I drank a lot and then I fucked a lot. I was loud and then I came. I mean, I think I came but all the drinks I had keep me from knowing with much certainty.

Waking up in his bed mostly sober and completely naked, things were a little different. I looked around the bedroom: mattress on the floor, the practically trademarked shade of Bushwick Pink walls, clothes covering the floor. Typical single 20-something room situation.

“What time is it?” I’m looking at the Lucha libre mask hung awkwardly high on the wall across the room from me. I bet that nail was already there when he moved in.

He reached to the floor next to him for his phone. “8 a.m.” What time had I gone to sleep? Was I really so wasted I had to fall asleep naked, with a stranger?

He didn’t seem annoyed that I woke him up early on a Saturday. My observation of the rest of his room is peppered with portions of the conversation his roommates are having in the next one over. Every word is crystal clear through the dividing wall — it’s safe to assume they heard everything that happened in this bedroom last night.

Carefully avoiding looking at the hair on his chest, the shiny white stretch marks on his belly and under his arms, I crawl out of his bed. Without the visual lubrication the booze had provided, getting dressed in front of him is far more awkward than my impending walk of shame back home. There’s no graceful way to sit as I pull on my skirt and button up the shirt from the night before. He’s polite, not leering and smiling as we make slow morning-after conversation. I make a note that his pretty teeth are just a bit too small for the rest of his face and decide I should obsess over that later.

Sitting on the edge of his bed, sliding my panties over my knees, it occurs to me that I have no idea who I’ve gone home with — not even the faintest inkling of his name. Guess this means I’m off the chastity wagon with a real bang, pardon the pun. I try to control the speed with which I’m getting dressed, now that I can hear his roommates stirring in the next room over. It sounds like they’re getting ready to head out the door and I’d just as soon not make contact before trying to find my way back home.

They’ve moved to the hallway outside the bedroom, but not without stopping in front of his door to holler “Bye, Shane!”

Thanks for the help girlie. 

They don’t head down the hall, the floorboards creaking under their weight while they continue to stand just outside of Shane’s room. “Bye, Shane’s friend!” She says it too loud, I feel the heat in my cheeks and even that makes my temples start to throb. This is going to be a rough recovery day, I can tell.

“Uh… bye?” I say. My throat is killing me from too many cigarettes and while I found my panties, I’m pretty sure my dignity is lost on the floor somewhere, too. Once I hear their footsteps on the stairs I put on my shoes. How do you exit a situation like this gracefully, again? I hand him my phone with the intent of getting his number before he can get mine. It’s 8 a.m. and I just want to go home, so I tolerate the kiss-hug combo he gives me after I tell him I’m leaving.

The false intimacy wigs me out, but he grabs my ass and I know there’s a 70/30 chance I could get a quick morning romp in before going home. But I don’t, and I’m thankful that I remembered my cheap sunglasses as I walk toward the train, vowing never to get into a cab with a stranger headed to Bushwick again. It’s not like I can ever really get lost in this city, anyway. Between Google Maps and creepy men on street corners, it’s not hard for a girl to get directions.

Stripping down to shower in my apartment, I spotted the marks he’d left on my neck and collarbone. “Fucking amateur,” I thought, “so glad he doesn’t have my number.” Despite the harassment of applying arnica gel and careful arranging of my hair to make it less obvious, I didn’t delete him from my phone. I went back and forth: was there any reason to talk to him again? Was there any reason not to? He’d put both his first and last name in my phone, which in my mind is little more than a thinly veiled instruction to Google someone. So I did.

The face on screen was still pretty cute now that I was completely sober, though his usual facial hair situation was significantly more bearded than when we met. Just a couple quick keystrokes and his internet presence unfolds in the browser window. Facebook (private), Twitter (not updated) and the jackpot: Tumblr. No lengthy diary entries but enough photos to gather some insight into what kind of shenanigans he gets into. I didn’t remember that he worked in photography, grew up on the west coast, or… had a neck tattoo. How I missed that last little detail on my way out in the morning is simple: avoiding eye contact and a distinct desire to leave with as little interaction as possible. I picked out a low key playlist from my iTunes to put on repeat and lay down, intent on getting some sleep before meeting up with friends.

My forced attempt at disinterest didn’t last long — by the end of the weekend I resolved to text him once so he’d have my number and take it from there. When I didn’t hear back for a few days I resolved that I’d effectively bounced back from my extensive “Chaste Waste” status. A week later he invited me to hang out, asking if I’d like to go get dinner with him.

I think we all know where this is going, right?

I told him OK.


Just wanted to see if you wanted to hang out again. Have dinner with me tonight?

It was Friday, and I was already eager to ditch the office for the weekend before he asked. I made it out of there in record time, already worrying on the train about what I should be wearing on this date. It seemed like a big one — the kind where you start out sober after already having seen the other person naked. This is so stupid, I thought while working my way through too many outfit changes before settling back on the first thing I’d picked out. For all I know this is going to be terrible and I’ll hate him. I reapplied my makeup, added a second coat of mascara. The tube’s packaging promised it would make every lash count, and it did. Good mascara is worth every penny, friends. He called as I was leaving to ask if we were still on for dinner. I didn’t realize there had been a question about our plans, but confirmed anyway.

We met up in Morgantown, an obnoxious way of saying that it’s a gentrified warehouse hipster hotbed that happens to be off the Morgan L. (I Googled it at work, because missing what I assumed would be a free dinner sucks.) I saw him from across the street, waving to me, dressed in pajama pants with a baggy sweater, his arm in a cast. An interesting new addition, for sure. He came closer, his facial hair a step beyond scruffy. During our weird hug hello I felt a little put-out. I shaved my legs and put on a skirt for this?

Seated at the long wooden benches in the sushi restaurant he had suggested, Shane told me he had hurt himself while saving a burning bus full of children and nuns before owning up to slamming his hand in a freight elevator at work the day before. After hearing about how long he’d been at the hospital, it dawned on me he had invited me out shortly before going to the hospital to have his hand checked out. A little weird, but it explained why he called to make sure I was still coming. We ordered too much sushi to finish and a couple beers, which was what finally allowed our conversation to flow without as many awkward gaps between topics. I debated fake-digging in my purse when the bill came, but he put down his card before telling me he wanted to take me for drinks.

He hailed a car and we had more drinks at a bar somewhere between his apartment and mine. I was a little drunker than I’d meant to be when he suggested we see Tree of Life together. It didn’t sound that interesting, but I pretended it did because I was having fun despite myself. I started browsing show times on my phone before telling him it was probably a bit late in the evening to make it to any of the theaters in the city.

He laughed. “I meant another time, darling.” Even drunk I felt stupid, embarrassed to have possibly seemed too eager to hang out again. He went on, smiling. “But I think it’s cute you got excited about it.”

I’m liking him more with each drink that I have — dangerous. After I set down my fourth or fifth empty glass he gave my knee a little squeeze. “Wanna get out of here?

Using the same line again doesn’t make it any less effective, and I’m ready to go before he finishes pulling money out of his wallet to pay our tab. We walked a few blocks with my arm in his before I get my bearings and see we’re headed in the direction of both of our apartments.

“Do you want me to walk you home?” I might be drunk but I know he’s asking if I want to bring him back to my place. I’m not into the idea of bringing a guy home — the first one I’ve slept with in nearly a year, no less, is too much to handle.

“No… but we can go to your place.”

It’s not a question, and he steers us south. I know I have brunch plans early — but he doesn’t live that far and I want to see what round two will be like. I notice that the floor of his bedroom is clear once we get back to his room. I’m pleased I don’t have to worry about tripping over dirty clothes as he undresses me in the dark.

Another drunken sexual escapade is had, without the same fervor of the first time. His chest hair changes from weird to hot and blowing him does as much for me as for him. He’s non-vocal and at points hearing my own sucking sounds makes me wonder if he’s having a good time. I stopped to ask but his voice returned quickly, and a lady should only make someone say please once before finishing the task at hand.

I fall asleep naked next to him after he comes in my mouth, too tired to put panties on like I usually would. When I wake up in the morning, I realize I am definitely going to be late for brunch and scramble to make myself presentable enough to walk out the door. The bodysuit that looked so hot the night before is stretched out and I worry one of my nipples is going to pop out on my way home.

“I have to go…”

“Yeah, you’re having brunch with your friend, right?” He lightly rubs my back and I’m uncomfortable with all the details he remembers from the night before. I’m quick to leave, as always.

The walk from the L off Bedford to the low end of Greenpoint did not work wonders on my stomach, not to mention my headache. I considered steering off into McCarren park to puke, but there were too many people running the track for me to risk them seeing. I like to puke in private, I guess. My friend was kicking it on the sidewalk out front when I walked up, praying she wasn’t mad but feeling too shitty to do much apologizing if she was. Giving me the once over, she smirked as she stepped away from the lamppost she’d been leaning on.

“So, how was YOUR night?”

“I can’t even start talking about this until I order a drink,” I said as we headed to the patio. After ordering a bloody mary, French press coffee and a glass of water from our waitress I continued, slightly worried that they wouldn’t arrive in time to save me from the hangover that was still building.

“Sooo… that dude I went home with last weekend took me out last night.”


“I dunno, I mean he’s kind of effeminate.”

“Well, yeah. I mean he went to art school in the south somewhere.”

“… he did?” I’m genuinely confused about how she knows this little crucially damning detail about him.

“He told us the night we met him, don’t you remember?!” she exclaimed, laughing loudly. After filling her in about the night before’s events she asked if I was excited for our next date.

“Ugh, don’t say that. Call it something else, like a hang out thing.”

“Why? It’s a date!”

I wasn’t going to win, so I rolled my eyes and we moved on to other topics.

Another Sunday, another late brunch. I walked into Roebling Tea Room with my friend closer to three than noon like we’d planned originally. All these artists and free-wheelers run on brunch time, and I can’t help but feel like this large-scale problem with time management is going to have a permanent effect on my ability to show up anywhere on schedule. We ordered from the waitress, she was one of those typical brunettes with greasy hair and skin you see all over Williamsburg and can’t tell if they genuinely don’t care about their appearance or just pretend not to care. My phone chirped from my purse as I told her I wanted an Americano. She makes a face as I reach into my bag to find it, though I wait until she’s walking away to unlock the screen. I’m not sure why she gave me the stink eye — I make a conscious effort not to be one of those people that texts/talks on the phone while speaking with my server. That’s just rude.

Still want to see that movie with me today?
Sure — at lunch with a friend now, but we can meet after.

My face half lost behind the big white mug, my friend made a comment about the mostly-faded hickey on my neck. While it’s technically the third Shane’s left on me, I decide it’s better to keep that detail to myself. The path the conversation has taken feels more accusatory than playful; I’m a grown woman, let me worry about what idiot I had on my neck a few nights ago.

“It’s really not as big a deal as you’re making it out to be.” Knowing what I’m saying is true doesn’t sway him from continuing to poke fun at me about it. Maybe his Jealousy-Vision made the mark more obvious. Regardless, I was confident that with the help of arnica gel and some cold spoons it would be gone by the time I got to work on Monday morning.

“Either that or it’s a strangulation mark from him putting his hands around your neck,” he continued. And now he’s taken it too far — I make a face and silently look at the people seated near us, like looking at them is going to make him shut up. Our waitress chooses this moment to drop off our plates and I facilitate my silence with big bites of my meal, chewing each one longer than necessary. I hadn’t gone into details with him about what had happened previously, he’s just one of those friends I don’t go there with. Needless to say, we parted ways soon after so I could meet up with Shane.

He met me a block away and we kicked around between concrete stoops until deciding on a late movie showing. There was only one place to go since we had a few hours to kill: the bar. Two rounds later we decided to mosey into the city, catching the J into the Lower East Side. We found ourselves part of a mass of spectators for a park-style basketball game off Houston, sitting on the steps to half-watch and talk. It almost looked official, the teams wore brightly colored team jerseys with matching shorts, their shouting friends and family members on the sidelines, sneakers squeaking on the pavement in a way I thought could only happen in a high school gymnasium. For an hour we watch the groups making their way across the street, talking about peripheral memory and what subcultures we identified with in high school.

He’s smiling at me again — he has such beautiful cheeks and all the doubtful thoughts I had about not liking him seem to vanish.

“Sooooo…” he draws out the syllables, “do you likeeeee… popcorn?” I’m smiling because he’s smiling and he’s smiling to make me smile. This is so fucking gay.

“I do.”

“What about snacks? Favorite movie theater candy?”

Feeder, I think. He hits the concession stand while I use the ladies’ room, buying a huge bag of movie popcorn with jalapeño powder, Reese’s Pieces and ginger ale for us to share. Good thing, because it was a LONG goddamn movie. Those two hours felt more like ten, and regardless of Terrence Malick’s acclaimed approach to film-making I was itching to get out of my seat long before it was over.

We walked around the city after, dissecting the movie. I was surprised he didn’t rabidly praise it, or maybe he just felt sympathetic. We stopped in a mostly empty bar with a half-ass pirate theme going on. They painted the exterior red and black and a chalkboard out front informs all passing wenches: PIRATE MIKE IS BEHIND THE BAR TONITE!!! Once we get inside we see PM himself, the giant gold hoop earring he’s wearing a dead giveaway. I know New York is full of artistes but I can’t help but feel tacky by association when he says “arr” and “lassie” as we ordered.

I paid for our first round and Shane makes some comment about the perks of dating older women, calling me “sugar mama.” This is the first time I’ve paid for anything, and I’m only doing it because I’m starting to feel guilty for never having even offered to before. He asked for the cheapest beer in a can; I don’t know if it’s because I’m paying or because he wants a shitty beer, but I’d like to think it’s the first one. Either way, I’m only a year older than he is and the “sugar mama” comment catches me off guard. God, do I look like a cougar? No time to worry about that now.

Picking out a corner booth, he scoots in first and I sit next to him. I hate that it works, but he showers me with compliments and they’re just the right ones to make me pay attention. Not that I’m pretty, not that I’m smart (I already know both things to be true) but he leans in and puts a hand on my bare thigh. “You’re so skinny.”

I blush.

“Svelte even.”

And smile.

“So… lean.”

My cheeks hurt and I hate that these are these are the kinds of words that elicit the best response from me, swellings of pride in my chest; as if I’m actually skinny enough for someone to comment on it. I work hard for my figure and it’s still nowhere near the Kate Moss level of perfection I secretly aspire to. The beer in front of me is probably why.

“Are you blushing right now?” He can see the dumb smirk on my face and he’s making it worse. I am relishing all this attention, the booze makes it easier to accept his compliments graciously. He teases me, running his hands lightly across the sides of my face while he talks about how he wants to take my picture. The fuzzy haze lifts a little; even the most casual suggestion of spending time in front of the camera is enough to snap me out of the moment we were having.

He turns over his right hand while gesturing as he speaks, and in the bar’s poor lighting I notice something new in the tattoo on his wrist. The shiny, raised presence of old scars mostly covered by a tattoo of an eagle — a slick camouflage technique more people seem to be picking up on. It almost worked, the flicker from the tea light on our table was the only light source that betrayed the difference between scar tissue and not. Did I find myself a Sad Boy?

I’m fascinated and catch myself looking at it whenever I think he’s not watching. It’s nearly 2 a.m. How did that happen? I have work in the morning and I probably shouldn’t have had so much to drink. Time to go back to Brooklyn. I would’ve been happy to take the train, but Shane insists we grab a cab. Once in back he asks if we’re going to my place. I pretend to be one of those girls who can’t read a map to avoid having him over. Why does he insist on trying to come over, anyway? We’re not nesting — this is only our third date.

And so we go back to his apartment, proceeding to have sex that I am even more sober/present for than the last two times. I am just comfortable enough to be giggly while we roll around partially naked on his bed. He stops as we fool around, face serious when he asks, “What’s so funny?”

“Nothing, I’m just… laughing?” I didn’t know sex had to be serious. I am not serious. We’re naked — serious is not an option.

He doesn’t look like he believes me. “Okay… as long as you’re not laughing at me, I guess.”

It was too raw of a moment for me, enough for a switch in my head to go off. I wound up on auto-pilot, not feeling anything below the waist despite his best attempts to get me off. I was relieved when he came and pulled out so I could pass out before overthinking what he’d said. When my phone’s alarm went off at 6 a.m. I was quick to get up and head home, not enthused about beginning my Monday with a serious hangover accompanied by a small but growing sense of guilt.

I thought after a few days it would alleviate, but it lingered. Was I hanging out with this guy for attention? Did I even like him? Probably not, I thought.

I called a friend I met off the internet back in California to gain some perspective. Jeff and I tried to date, but it just didn’t pan out — between the two of us there were enough commitment and intimacy issues to sink a sailboat.

“So you’ve been seeing someone, I gather.”

“Well… I wouldn’t take it that far. Aside from going home with him after getting wasted we’ve been out twice. He’s from Orange County.”

“Oh, so he’s awesome like me!”

“I guess — he’s some art school kid, though. I feel like the only person on the entire east coast that didn’t go to fucking art school.”

“Quit trying to derail the conversation. Are you into him? Or are you doing that thing we both do?”

“What thing?” I asked, knowing where he was headed with this.

“Get stoked on someone, then pull away.”

“Oh… yeah, definitely doing that. He’s just too nice to me, y’know?”

“I know the feeling, but Christ.”

“I know! It’s the stupidest thing ever,” I say. “I just… I can’t help it.”

“I mean, I get it.”

“Like really — he’s great. I’d even say he’s sweet… yet I’ve been trying to convince myself I hate him for the last week. This is the first dude that’s been relatively normal and interested in me in the last two years. What if I’m going along with this out of… not duty, but out of some need to just feel desirable? That’s not fair. That’s not a good reason to keep seeing someone, you know?”

“I can’t tell if you’re venting or asking for advice. But I’m going to drop a little nugget of wisdom on you, since I just went through something like this: you think you know what you do, or don’t, like in someone. Sometimes instead of trying to look for qualities someone possesses — like being tall, or sort of a jerk, or having nice teeth or whatever — you should thinking about how you feel when you’re around him.”

I didn’t say anything, waiting for him to continue giving me advice I could tell I wasn’t going to follow.

“Just… try something different for once, okay? Even if it makes you uncomfortable and feels ‘wrong’ at the time.”

I hate the suggestion, and he could tell from the lackluster “okay” and “uh huh” responses he was getting from me at the appropriate pauses in conversation. Before hanging up he made me promise to see Shane one more time. “Just to make sure you’re not freaking out over nothing,” he said.

I wanted to believe Jeff was onto something, that he had just talked me out of blowing off what could’ve been the next best thing in the series of events that made up my newly rekindled desire to get involved with men.

But he didn’t. TC Mark

image – Shutterstock

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