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Eating Boston: Day One, Part Three

The Lenox Hotel was our second choice of accommodations for the weekend and, after some spirited negotiations between Shannon and the staff at each hotel via phone and email, she finally announced the Hotel Commonwealth had won the honor of our heads in their beds. The Lenox graciously offered her a $200 voucher to spend at either the bar or restaurant within the Lenox as a “thank you for playing maybe we will get you next time” parting gift. With a double sawbuck head start, our plan was to go there for dinner, burn through the voucher and then see what more trouble we could uncover in the city. We began walking to The Lenox, stopping at a few stores on the way, but were disappointed to discover that City Table, the restaurant within the Lenox, was closed for a party. Being flexible, we decided to go to the Lenox watering hole, City Bar, have a drink and work on another plan. A few glasses of wine and bourbon later, we had no plan as well as a good deal of money left on the voucher. Kyle and I suggested we visit the cigar bar we had passed, located across the street, stressing it was neither a store nor a restaurant so it could count as something new. Shannon and Hope declined our offer, unfazed by our enthusiasm, but sent us on our way with their blessing. They had found peace at City Bar and liked the challenge of spending the rest of the voucher on appetizers and wine. Kyle and I were confident they were up to the task and we left them to work their sketchy plan.

Cigar Masters on Boylston Street (which, I am sad to report, is now closed) at seven p.m. was exactly as we imagined. A long, thin lounge shrouded in dark wood and mahogany furniture, bookended with  overstuffed sofas in the front and back with a humidor and bar anchoring the center. Kyle and I perused the cigar selection, purchased two 60 ring options and settled in at the bar. There were televisions within site, one showing college football and the other locked into the NFL Thursday night game preparing to kick-off at eight. At this moment, testosterone was redlining and endorphins were flooding our brain. We were happy. So very happy.

We decided to get a drink and the female bartender, apprised of our situation, convinced us that a flight of port would be a perfect way to slowly enjoy the evening. We agreed but were a little concerned when the flight landed and each glass was half full, not the usual dribble in order to get a taste of the liquor. Fortunately we were sharing. The first glass held a port aged ten years, the second was aged 20 years and this pattern continued for two more decades. We worked on the content of the glasses slowly, and in order, and, as the bar began filling up, we realized how fortunate we were being early birds and securing a seat. The night was uneventful, just two brothers watching football, smoking cigars and sipping sugar sweet booze, pleased with our choice of venue. I even had my shoes shined by the resident shoeshine man who had set up shop toward the back of the bar. We were men doing men things. All was well and my shoes reflected what little light was in the bar and matched my spirit.

After three hours, the ventilation system in the bar began struggling with the slab of smoke created by the burnt ends of many cigars pushing against the ceiling. With each breath I could feel the rash food and drink decisions of the day start to rebel. The phrase “feeling green” slowly moved from apt metaphor to grim reality. Soon, the wives began texting us, wondering where we were and I was relieved when we decided to leave and meet them outside. It was after eleven o’clock and the marathon day had started taking its toll. Inhaling deep, cool breaths of fresh air did wonders for my all-around well-being and I began feeling the benefits immediately; my verdant tint was fading. That abruptly changed when the ladies suggested we go back into Cigar Masters for a nightcap before heading back to our hotel. I knew it wasn’t a great idea and I put up token resistance but ultimately followed everyone back in and sank slowly into one of the leather sofas. While they all enjoyed a final drink, I sat with my eyes closed and my arms crossed, trying desperately not to inhale the thick air, concentrating on quelling all that was going wrong within my shell. By the time we left I had turned a corner and I knew what was waiting at the end of the block.

I held it together in the cab and in the lobby of the Hotel Commonwealth and even held it together for an hour once in our room. But it was a false hope, one that erupted along with everything else for the first time around one a.m. It was a long night but the bathroom was very fancy so that took some of the edge off. It also gave me plenty of time to recalculate my approach to the first day in a new city on vacation. The phrase “pace yourself” was on loop in my brain. I also considered turning the phrase into a tattoo so this would never happen again.

Published inThe Pursuit of Happiness

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