Clearly, I Didn't Think This Through : The Story of One Tall Girl's Impulsive, Ill-conceived, and Borderline Irresponsible Life Decisions (9781101612255) Read online

  That was where Details magazine came in. It was my window to a man’s world: how they thought, how they acted, how they dressed. Reading it felt like I was taking a peek inside the guys’ locker room. The next best thing I had to a steady man in my life was my monthly subscription to Details. At least that came regularly. It’s crazy to say, but sniffing the cologne samples on their pages was the closest I got to smelling a real live human man. I read every issue cover to cover, like a Bible with pictures of hot dudes on every other page. I especially enjoyed the articles about sex because although I wasn’t having it, I was fascinated by people who did.

  Everyone says that your college years are the most carefree, wild times of your life. My college experience was the polar opposite: I was sitting in a dorm room sniffing Polo Sport from a piece of paper trying to experience the thrill of masculinity through osmosis. Put that in your brochure, Barnard.

  I didn’t even go on a real date until my senior year of college, just a few weeks shy of my twenty-first birthday. The lucky man? A scrappy guitarist named Tommy. His doughy, round body was covered with tattoos, and his black spiky hair was thin yet somehow always oily. Even though he was only twenty-six years old, he had a beer belly, which freaked me out. Apparently, we’d met a bunch of times but I didn’t remember the details of those encounters.

  So no one was more shocked than me to hear his voice on the other end of my phone. One bright February day, he tracked down my phone number and called me out of the blue. I was in the kitchen making lunch when he called.

  “Hey. Is Anna there?”

  “Yeah, this is she,” I said, slowly. “May I ask who’s calling?”

  “This is Tommy!”

  “Tommy?” I didn’t remember giving my number to anyone named Tommy.

  “You know, Trish’s friend? I play guitar in Hellbent. We’ve met, like, a bunch of times before.”

  “Oh, Tommy! Yeah, I remember you.” He could probably hear my wheels turning as I tried to place him.

  “Anna, we’ve met a bunch of times before.”

  “Really?”

  “Yeah. Like, at least five times. Think hard.”

  “Riiiiiight. Tommy!” I pretended to know who he was to keep things moving. “How’d you get my number?”

  “Trish gave it to me. Well, scratch that. I made her give it to me.”

  “Why’d you do that?”

  “Well, I was just wondering what you’re doing tonight. I thought maybe we could go out.”

  “Go out? With me?”

  “Yes! Is that weird?”

  “No, it’s not weird. Let’s see. What am I doing tonight? Gosh, nothing?” I twisted the phone cord around my finger. “Is there anything fun going on?”

  “Well, there are two parties tonight. One is in Brooklyn. Some kid I went to school with at NYU named Kyle is having a house party. The word on the street is that it’ll be fun. The other party I heard about is in a loft in midtown.”

  “Okay.” I weighed the two parties out in my mind, with no real preference. I was still processing the fact that a guy had called my phone number on purpose. And I was also processing how great his voice was. It was a deep voice, a man’s voice. I don’t think my phone had ever entertained a voice that deep before. I had to sit down.

  “I’m leaning more toward heading to the party in midtown,” he said.

  “Oh yeah? Why’s that?”

  “Because it’s closer to you.”

  I blushed so hard that my face got hot. I unzipped my sweatshirt.

  “Why don’t I swing by your way and pick you up?”

  “Up by me? No, I live in Morningside Heights. That’s practically Harlem. Where do you live?”

  “I’m in Brooklyn. Like, five stops off the L train.” I didn’t know much about Brooklyn. All I knew was that it was far.

  “That’s sweet, Tommy, but it’ll take you at least forty-five minutes to come up by me. How about I just meet you at the party?”

  “Anna, I want to be a gentleman about this. You know, pick you up and stuff.” It was nice that he wanted to display any kind of chivalry toward me, but the thought of an awkward subway ride down to the party together seemed like it would make my head explode.

  After much protesting on my part, he finally agreed to meet me at the loft party at ten thirty P.M. This was the first date I’d had since high school. I panicked. I hopped in the shower and deforested both my legs and my armpits. For this, my first date of 1999, I settled on dark blue jeans and a fuzzy, tight pink turtleneck that I’d scrounged from a thrift store. That, coupled with my dyed black hair and Betty Page bangs, made me look like an indie rock starlet. The weakest area of my outfit was my footwear, a clunky pair of Merrell hiking boots. It was the only pair of shoes that I owned as I have an aversion to any sort of a high-heel situation. Since my toes are the approximate size and shape of gnocchi, they can’t fully support my body when I wear anything higher than a flip-flop. I topple over like Jenga. What my hiking boots lacked in sex appeal, they made up for in comfort, which was great news for running to class, but a bummer when trying to look cute on a first date. I really hoped he wouldn’t look at my feet.

  After double-checking that I had my keys, wallet, and lipstick, I hopped on the train and headed downtown to meet him.

  The party was in a huge loft space where the walls were painted white and neon pink drapes framed the large windows overlooking the city. Everyone stood around and looked bored, which New Yorkers are great at doing. Techno music blasted out of two speakers propped up on one side of the room. I didn’t recognize anyone there. I figured Tommy was the guy walking toward me with a wide smile on his face. He was wearing a navy blue hoodie, jeans, a brown wool coat, and had a brown messenger bag slung across his chest.

  “Anna! You made it! Did you have any trouble finding the place?”

  “Nope. None.” I looked him over. Ah, Tommy! Now I remembered meeting him. Sort of.

  “Wow! You look ravishing.” He scanned me up and down. “Seriously, you’re gorgeous.” Since I wasn’t used to receiving compliments, I decided to argue with him.

  “No, I’m not.”

  “I love that sweater. It fits you perfectly.” He reached over and rubbed my sleeve.

  “No, it doesn’t. In fact, I think it’s a little tight.”

  “Seriously, you look beautiful.”

  “My hair looks stupid.”

  “Your coat is great, too.”

  “I only paid two dollars for it.”

  “Anna, just say, ‘Thank you, Tommy.’ Try it.”

  “Thank you, Tommy,” I conceded.

  “There. Was that so hard?”

  “So, what do you think of this party?”

  “Well, I just walked in but so far, it seems okay. Can I get you something to drink?”

  “Actually, no, I’m fine.” I’m fine.

  “You sure? They have an open bar.”

  “Yeah, really. I’m good.”

  “Wait, you don’t drink, do you?”

  I shook my head no. “How’d you know?”

  “Trish told me.” He’d really done his homework. I was impressed.

  “It’s all true.” I shrugged.

  “Well, we’ll see how long that’ll last once you hang with me.”

  “Good luck with that. I can’t see you breaking me of this nondrinking habit anytime soon.”

  “So, you don’t drink. We can’t go to a bar then, can we?”

  “I’m only twenty; I couldn’t get in even if we did go.” I was starting to feel bad. He couldn’t take me anywhere.

  “Oh shit! I forgot! You’re young, too.”

  I honestly couldn’t think of one other place to go. A restaurant? A club? I didn’t know of any other parties. Plus, we were in midtown Manhattan where unless you’re going to a ballet or a museum, there isn’t much to do past eleven P.M. Finally, I suggested, “Do you just want to go back to my place?” His eyes lit up.

  “Anna, are you hitting on me?”
>
  “No, I-I…just thought that…” I stammered. “I mean, if it’s too weird—”

  “Don’t worry your pretty little head about it. Let’s go.” He took my hand and we left. Normally, I would never take a guy home twenty minutes into our first date, but I had no idea what I was doing. I’m going to plead ignorance on this one. I was just thinking that we’d go back to my room and hang out because that was what I’d done in high school with my boyfriend. I had no idea what Tommy thought my asking him back to my room meant. That stressed me out, too. Did he think we were going to bang? As soon as we stepped foot on the 9 train heading uptown, I started to panic.

  Tommy was the first guy I’d ever taken back to my dorm suite. I shared the spot with four friends. And they were all in the common room eating pizza when I walked in with him.

  “Hey, guys. This is Tommy.” They mumbled a few low hellos as I pointed each of them out to him. “That’s Julie, Kate, Allison, and the one over there is Maria.”

  “Good evening, ladies.” He waved. The room was dead silent. They all exchanged looks. Maria stopped chewing altogether and just had her mouth hanging open in total disbelief that I’d brought a guy home. “We’re going to hang out in my room now,” I announced.

  “It was nice meeting you all,” he said as we walked the ten feet to my corner room. That was when I realized that my bedroom was in no condition to entertain a man. I made him stand outside in the hallway as I did a quick five-minute cleanup. I jammed my dirty scattered clothes on the floor into the closet. I straightened up my desk. I made the bed and did a quick spritz of my perfume in the air as a makeshift air freshener. As a final touch, I put a Specials CD on the stereo, you know, to set the mood. Why I picked a ska band, I’ll never know. Let’s just say that the vibe in my boudoir was definitely upbeat.

  “Okay, Tommy. You can come in now,” I shouted through the door. He gingerly twisted the doorknob.

  “Are you sure it’s safe to come in? There’s no, like, dead hookers here or anything, right?”

  “Nope! I put them in the bathtub. My bedroom’s all clear.”

  “Sweet place!” he said, sizing it up. He looked at the band posters tacked up on the walls and nodded in approval.

  “Yeah, I do what I can.” He dropped his dirty brown messenger bag in the corner and kicked off his shoes. That was when it became clear to me that he took no pride in his sock situation whatsoever. Not only were his socks mismatched, but they had holes in them. It was like he had no quality control in his foot underwear at all; any old piece of cloth somewhat shaped like a foot must be granted permanent residence in his sock drawer.

  Clearly his socks were the fruitcake of his wardrobe. They were probably a present from his aunt or something. And I bet that they would never get tossed out even though they had catapulted past their expiration date. I’d have bet that he needed to give at least seventy-five percent of his sock collection the boot. Instead, he’d just wear them until the threads peeled away from his foot in total despair. The ones he had on his feet were thin, and any trace of elastic had long since abandoned the effort, so they slouched around his ankles like a kid being yelled at by his parents. The holes by the toes were especially pathetic, like his feet were auditioning for the role of Tiny Tim in a community play. I briefly considered passing around a Pepsi can in the common area to scrape up enough money to get him a six-pack of athletic socks at Target.

  That was when it hit me that I finally had a guy alone in my room, slouchy socks be damned. It was like having a wish granted by a genie or a charitable foundation. Sure, Tommy wouldn’t have been my first choice. Yes, he looked like a warthog, but it was a bit of a beggars/choosers situation and I wasn’t going to start splitting oily, black hairs about it. And, I have to say, I was warming up to Tommy. He made me feel pretty.

  “So, you’re in my bedroom.”

  “I am.”

  “What do you want to do? We could listen to some records.”

  “Actually, I’m starving. Do you have anything to eat?”

  “Yeah. Hang out here. Make yourself at home while I fix us some snacks.”

  “Can I change the music?” I guess the ska wasn’t doing it for him.

  “Absolutely. Put something nice on.”

  I saw my roommates on the way to the kitchen and they all basically flipped their lid.

  “Who is this guy?” Allison whispered loudly.

  “Oh my God, are you guys going to do it?” Maria giggled.

  “You’re gonna get so much action tonight. Holy shit.” Allison was trying to contain herself. Kate pretended that she was humping the air, and then she whispered, “That’s totally gonna be you tonight! Ha!”

  “Shhhh! Keep it down! He’ll hear you. I’ll tell you all about it later, I promise.” Before I headed back with a few slices of frozen pizza I’d burned in the oven, they all high-fived me like I’d already scored the touchdown. Cool; I had my own cheerleading section.

  When I came back, I found him sitting on the edge of my bed playing my guitar. I stood in the doorway for a second, watching him noodle around. He clearly had some chops.

  I smiled. “Wow, I didn’t know you could play guitar that well. That’s great, Tommy.” But he didn’t stop. He started singing. And that was when it got weird for me.

  It was like John Mayer possessed his body or something. He closed his eyes and started hittin’ some high notes. When he finally opened his peepers, I think he tried to make meaningful eye contact with me while he was singing.

  I didn’t expect him to know this since it was only our first date, but I hate when people look at me when they’re singing. It makes me self-conscious: Should I return this meaningful gaze? Should I sway back and forth with a lighter in the air? Should I burst into tears like a Beatles fan in the sixties? He had just turned my cozy bedroom into open mic night at the Peach Pit. I’d have totally smashed the guitar to put an end to this impromptu serenade like John Belushi did in Animal House, except that it was my guitar and, yeah, I wasn’t going to do that.

  I wondered if this was something he saw in a movie as a slick move to “seal the deal,” which made me panic even more. Honestly, I’d have preferred it if he left the singer-songwriter act for the street performers in the park.

  But I didn’t tell him that. I just waited for him to strum the last note and said, “That was really lovely, Tommy.” I handed him his burnt pizza.

  “Aw. Thanks, Anna. You’re the best. You know I sang that song for you.”

  Then he kissed me, which I liked so I didn’t have to keep babbling about the song he just sang. He forgot all about the pizza I just gave him. He placed it on the floor and pulled me onto my bed. I must say, he wasn’t a terrible kisser. It was pretty nice, actually.

  “Hey, you can sleep over if you want, but is it okay if we just kiss for now?” It took all of my courage to ask him to stay.

  “Of course! I’d really like that.”

  “Cool.” I kicked off my giant shoes and they landed on the ground with a thud. By the time I shimmied out of my turtleneck sweater, he had already peeled off his clothes and was in his boxer shorts. He must be a part-time male-stripper because he just flipped his outfit off in one fluid motion. Then it dawned on me: I had a semi-naked man in my room. Holy shit. His ding-dong was on my twin bed. I wanted to get a commemorative plaque or something. Here lay a man’s penis once. I couldn’t wait to tell my roommates.

  However, as excited as I was about the ding-dong situation, it occurred to me that I wasn’t wearing anything that could be remotely considered sexy underwear. I only owned high-cut full-coverage briefs in dark colors. I’m pretty sure sumo wrestlers had sexier underwear than me. See, here’s the thing: I have a flat ass, no hips, and a bit of a tummy. Anything other than medical-grade elastic secured around my natural waistline would flop straight to the floor otherwise. And, it’s not a sexy panty flop; it’s more like the way salsa drops off a tortilla chip onto a carpet.

  As Tommy tugged at my jea
ns, I tried to quickly fashion my unfashionable panties into a makeshift bikini cut by pushing the elastic waistband down closer to my hips. Now it looked like I was wearing an exceptionally baggy bikini brief, which, I reasoned, was better than looking like I was wearing the bottom half of a 1920s-era swimsuit.

  We stayed up all night kissing and talking. He had a sharp sense of humor. But, more important, he was attracted to me! Just by that fact alone, I had to consider him as a contender. Maybe I could learn to love his beer belly. It wasn’t that bad. I’m sure it’d make a nice pillow or something. He said he adored my long legs and my green eyes and my soft skin. I was like, “This skin? It’s all right, I guess.”

  “Don’t do that,” he snapped.

  “Do what?”

  “Try to talk me out of liking you. You can’t do it. It won’t happen. Did anyone ever tell you that you talk too much?”

  “Ha! I guess I do.”

  “No, I’m telling you that you do. Just relax. I’m not going anywhere.”

  And I believed him.

  He watched me get dressed in the morning with a big, goofy grin slapped on his face. He really seemed to be enjoying himself with me. I, however, was a nervous wreck. My brain was on overdrive trying to figure out a million things simultaneously: Are we dating now? Are we official? Do I want to date him? Am I attracted to him? What would my family think of him? What would my friends think of him? Where is this going? Do I have time to fall in love? Am I ready to fall in love? Could I fall in love with him?

  “What’s wrong?” He sat up in bed, the sheets loose around his waist. “Stop pacing around. C’mere.” I sat down about a foot away from him on the bed, but he wound his arms around my waist and pulled me closer. “Have I told you how beautiful you are today yet?”

  “Only about a million times.”

  “Because you are.” I blushed at that. “All right. Let’s get brunch. I’m taking you out.” We strolled over to Tom’s Restaurant on 112th Street because he recognized the place from Seinfeld. He said that he’d always wanted to go. We held hands as we walked to the subway. When we parted ways, he promised to call me soon. I had learned nothing from my fling with Wyatt: In my mind, Tommy and I were now in a serious, committed relationship. He called two days later and asked me out to dinner. I had homework to do, but seeing Tommy sounded like more fun so I agreed to meet him.