When I was thirty years old, I played at dating like I didn’t have a lot of skin in the game, or so I liked to say. I had pined for a few guys in the past and hated it--that exposed, out-of-control feeling. Why would I ever chase again? I wanted--needed--to be in control to keep disappointment at bay. I needed to call the shots.
When I paid attention, men were easy to read. I knew the ones who would do the pursuing and the ones who needed to be chased. I was not like most women; the things they wanted, I didn't. Marriage and babies had been moved off of my agenda. I wanted a career and I wore that fact like a badge, until I stopped playing at being the tough girl and fell in love.
The night I met Jeff had been one of those long-awaited, warm nights that arrive in Boston in late May. Thursday night at Tavern on the Water--the only waterfront bar in Boston at the time--was the place to be from the start of spring until the end of summer. The Tavern was located on a pier in the Charlestown Navy Yard that offered full city views of Boston. As soon, as it was warm enough, the Tavern opened its sliding glass walls so patrons could spill out onto its wrap-around deck and breathe in the open sea air. The inside had a nautical feel, giving a nod to the decommissioned navy-yard-turned-residential marina. My roommate and best friend Paige and I frequented the Tavern with too much regularity. The doorman stopped checking our IDs and greeted us merely with, Good evening, sweetheart, in his rough Boston accent.
One night, Paige and I were meeting our friend Brad for drinks. We arrived first. We entered the bar and scanned the room for a high-top table, however, all of the glass walls were open, so available tables were sparse. In the corner, I spotted the dark-haired guy whom I had briefly chatted with the previous week.
As we walked by, I directed my gaze to him and slowed just enough to say, "Hey, you're the guy I don't know," with a hint of flirty confidence. Back then, I could conjure up a flirtatious hello like a reflex. The previous Thursday, I had seen him at the Warren Tavern, another local Charlestown bar. We had locked eyes in a weird, frozen moment in time--a movie moment, a friend would later describe it. He had looked familiar the first time we met, or so I thought, but I couldn’t place him. “I think I know you from somewhere,” I had blurted out. We had talked briefly, not even properly introducing ourselves. Tonight, he still looked familiar, or maybe I just wanted him to be because he was handsome, like Ralph Lauren, American-yacht-model handsome. He had dark brown hair, chestnut eyes, and a perfectly angled face. He smiled and waved. Paige gave me a glowing smile. “He’s cute! You should go talk to him!”
“You mean talk to him again?” I corrected.
“Yeah, go chat him up for real this time,” she encouraged. I loved Paige’s energy for everything. She had a different I-don’t-give-a-fuck attitude than me. Hers was all about never missing an opportunity for fun, whereas mine was, more . . . a fear of not being strong and brave.
“Ah, yeah, no. I don’t think so,” I said, dismissing the idea.
We found a spot at the bar, perched ourselves on the wooden stools, and ordered our regular drinks; white wine for Paige and a Midori Sour for me. It was green and grossly sweet and I loved it. We began the ritual of discussing work and all of its annoyances, my recent break-up from perpetually-late Lucas, and the details of Memorial Day Weekend in Newport, which was in a couple weeks. A friend had a house just off Thames Street, and we planned to go because we had declared this was going to be the Summer of Fun.
Brad showed up, and he blended in with the general population of white, Irish Catholic males in Boston. He was wearing his Rolex as usual--his hint to the world that he made good money. The watch had been a celebration gift to himself when HotJobs.com had been bought by Yahoo.com. The watch and his Porsche.
“What’s going on?” he asked in is his usual slick, almost salesy, way. Brad was an old friend from Connecticut. We had actually gone on a date, maybe two, depending on whom you asked, almost ten years ago. Ironically, I bumped into him in an elevator in Boston and we settled into a mutually-agreeable friendship.
Without missing a beat, Paige chimed in. “I think Melissa should go talk to that guy at the corner table.” She glanced in the direction of the guy.
“So, you can stop that,” I said refusing to look in the direction of the guy. Brad glanced over.
“Yeah, do it. Why not?” he asked, casually. “Guys do it all the time.” He signaled the bartender over.
“Stop making a scene, and no, I’m fine. Really. I don’t know him. We have already established this,” I reminded Paige, as she had been with me last week.
“Right, but didn't you say it’s on your list of things to do before you die--ask a guy out? Now’s your chance.”
“Do it, Marshall. I dare you,” Brad said.
A good number of my male friends called me by my last name, Marshall. I always assumed it was because it suited my just-one-of-the-guys demeanor, but maybe it was just a guy thing.
I hated and loved dares. They spoke with very little logic but whispered directly to my “prove yourself” ego.
“Double dare you,” Paige added as she looked over at him again. “Oh, he’s by himself. Go now, before his friend gets back. It’ll be easier this way.”
She was right--asking him out would be better to do without an audience. Take the dare. It’s now or never, the voice in my head said. There was something about this guy; I wanted his attention, even though it seemed I would need to grab it.
I thought of the time I had participated in the AIDSRide, which had been another dare. That was hard for 275 miles and three days; this would be hard for only a minute. Three years ago, in this same bar at just about the same time of year, I had entered into a bet that had been life changing.
“You guys could never do that,” Owen said to my co-worker Fiona and me, pointing to the back wall in the bar.
“Do what?” I asked. On the back wall was a poster for the Boston to New York AIDSRide. I looked at Fiona; we had been smack-talking about how we were more badass than Owen, the owner of our dotcom startup. He was always bragging. Fiona and I had taken it as our duty to call Owen out on his bullshit or at least try to put him in his place as often as we could.
“Screw you, Owen,” I said, smirking, “Let’s do it, Fiona!”
“I’m in,” she agreed.
The next day, I bought a bike, and five months later, Fiona and I--along with my childhood friend, Josh--rode our bikes 275 miles with 3,000 other riders, from Boston to New York.
On that day, nearly three years later, I didn't know that asking this guy out would end up being one of those life-changing moments. I took a breath and agreed to the dare for the bragging rights. I hopped off my barstool. To say I had butterflies would have been an understatement; I had to fight to keep from throwing up on myself.
As I stood, I adjusted my clingy t-shirt and smoothed my jeans, making sure no bulges showed in places they shouldn’t. I was glad I had on my favorite nude, strappy-heeled sandals--they made me taller and my legs look longer. I was still biking a decent number of miles per week, but every little bit helped. Within a few steps, my eyes locked with the guy’s--he knew I was coming to his table. Shit, it’s go time. Adrenaline coursed through my veins giving me the jitters and warming my skin with the heat of embarrassment. There was a fifty-fifty chance I was about to be rejected. Or maybe there was an even higher chance of rejection because if he had been interested, wouldn’t he have made a move last week?
"Hi, I'm Melissa," I said. I was probably shaking. I held my breath and tightened every muscle in my stomach to calm the fluttering feeling. To this day, that moment may have been the best core workout of my life.
“Jeff,” he said. His smile was easy--not arrogant--and his direct eye contact made the moment the tiniest bit more manageable. Some guys were obvious and awful when you first met them, in the way they looked you up and down, inspecting you. Not hiding that they were assessing your worthiness or, worse, your ability to make them worthy.
“Do you remember me from last week?” I asked.
“I do,” he said, holding my gaze.
“Well, I was wondering . . . if maybe you had a business card? I’d like to call you sometime. Maybe go out?” I said, sounding every bit the part of a scared little girl.
The words were out, and, oh my God, how unsmooth! That was not how guys asked girls out! I was the loser in a John Hughes movie. Maybe I could leave the bar right now. I should have rehearsed something in my head before walking over there. As I stood there in my high-heeled sandals, I suddenly felt like a loser on display wearing stilts.
"I don't have business cards on me but have a seat. Have a drink with me. My friend and his wife will be joining me soon," he said. Ugh, another female to judge how stupid I sounded. Excellent, I thought. But still, I smiled. I was here and committed, so I agreed and sat down on the empty barstool next to him. I could see Paige and Brad across from where we sat. Paige had on a giant smile, and Brad was giving me the subtle guy approval—a half smirk that controls a restrained smile. Once seated, it was as if I had just made it to the other side of some vast divide, and I was safely hanging onto the ledge. But the water still felt rough, and I was taking splashes of it up the nose every now and again as I kept replaying my clumsy introduction in my head.
Jeff and I returned to the previous week’s I think you look familiar conversation until we got to the bottom of it. We may have shared what I call "sliding door moments." Jeff and I used to live in the same apartment building for about six months in the Charlestown Navy Yard. Most people who lived in the Navy Yard took the commuter boat in the morning across the harbor to the State Street dock to get into downtown Boston. Even further back, Jeff went to Yale and would hang out at the Toad, a local New Haven bar. I was not a stranger to the Toad as I had grown up in Connecticut and that bar was well known in southern and south western Connecticut. It seemed plausible we crossed paths.
Jeff had recently bought a condo in South Boston--two blocks from where I was currently living. I joked it was his destiny to keep chasing me. Ian, Jeff’s friend returned with his wife Julie. Julie was a bit shy but politely engaged in our idle conversation, the kind that often develops for the sake of a new person--that person being me. I liked how she listened to everyone speak with genuine interest. I liked her ease with herself; it made me less nervous. Ian and Julie were a completely normal, non-scary couple. My fear of being judged dissolved right away.
Jeff gave me his phone number and after a reasonable amount of conversation and time had passed, I explained I should get back to my friends. I said my goodbyes and returned to my seat at the bar with Paige and Brian.
“Jesus, I’m glad that’s over! I never want to do that again in my life--that was awful. I still might be sick,” I said, but I was proud of myself and couldn’t believe I had just done that.
“Nice job,” Paige said, “You seriously have brass balls--that was awesome!”
“Good job, Marshall,” Brad added, raising his glass.