50 First Dates: III


Tequila. Taxidermy + Tonsil Hockey. At Tom + Jerrys.
I felt his energy as soon as i walked in. We locked eyes immediately as i sauntered into Tom + Jerry’s in my sundays best, leggings + sneakers and a little sweaty from teaching just prior. Jack looked both naughty + nice. His energy met mine + it didn’t take long before we were twirling + dipping all over the dark dirty bar, tripping on the dogs they let in + simultaneously salivating all over one another — with total disregard that we were both there entertaining our employees. Way to keep it professional Olivia. Oops. It took me 31 years to make out with a random guy in a bar, no joke. But feeling is feeling and i really wanted to feel him, even though he wreaked of cigarettes, was drunk enough to reveal he had a date waiting for him at home + simultaneously opened his heart.

A boy dressed in men’s clothing, with strong hands and puppy dog eyes that pierced into mine. I’ve always liked those, the bad boys who get close enough quickly to reveal hints of hope, grab you in all the right ways, and leave you wondering why. An hour in and our respective employees found entertainment of their own as we found a way to cuddle on one bar stool, sip tequila, salivate + share stories. I listened to his family history, successes + failures, and considered his invitation to thanksgiving dinner and his promise to cook for me the following week after date night at the movies. Slow down sexy, I said. I know your type: hot to trot with fast future plans and no follow thru, suave enough to lure you in + smooth enough to let you go.  I’m good at those. We went to dinner once more – he was nervous but warmed up over Shuka kebabs, too much garlic + too little care to resist ferociously making out out tableside like teenagers, all while offending the hummus having families seated nearby. My heart skipped a beat as I jumped in a cab home to awake for a 6am sweat before a 7am filming. Jack checked in the next morning, and then blamed food poisoning for his disappearance a week later. The next time i saw him was at his office, for coffee with his CEO, who i also met the night of our tonsil hockey tournament. We certainly put on a good show for Tom, Jerry + our teams. As for Jack, a playboy no doubt, but if i ran into him- i’d let him twirl me again, and leave it at that. No emotion necessary. There was something dark + deep layered beneath his brash exterior and emblazoned ego that briefly left me hungry to see his hiding heart. but I’m left with a note to self: Olivia, no matter your appetite, stay away from dark eyes in dark bars whose insecurities are not yours to mend or fix. So when he texted me last week to say he’d be back at our hunting ground, I simply responded with a photo: “hey stranger, im busy eating chicken with my hands at home. no taxidermy for me today. have fun.” and i’m sure Jack and his dark eyes did just that.

Brad the entrepreneur

Seems we’re in this entrepreneurial era of everyone seeking funding to follow their dreams, and as such I met brad thru his fundraising deck. i had a fantasy that while fundraising id either meet an investor or a husband. neither has happened, so i stopped hunting for both. I responded to Brad’s pitch out of courtesy and he resplied two months later to connect. After a google search revealing his attractiveness and the self awareness that i was thirsty, i agreed to meet at the Crosby Hotel late morning.

Coffee meetings are business meetings in my book, so I wore business attire, a Kelly green St. John knit jacket + ready for anything confidence. Brad swooped in a bit late, with an unshaven face, and unabashed confidence exuding from his unbuttoned shirt. Masculine, educated, self aware, sexy and just slightly unrefined...i quickly became even more dehydrated. Business meeting quickly became deep discussion - both us speaking the same language, although English is his second. I was turned on + so was he, but we were both also late for our next meetings. #startuplife - So brad + i said ciao for now. Weeks passed before he insisted on drinks on a rainy afternoon after a long day, but i obliged before attempting to cancel 3x. we agreed on ATLA, although I was not dressed to impress, but quickly distracted by a mezcal negroni, our mutual joie de vivre and a messy makeout at the place i hold lunch meetings multiple times a week. Way to keep it Professional, olivia. Day turned into darkness + we sauntered to tom + jerrys for a nitecap in the rain, a bar better suited for messy make outs no doubt. But i played it cool + dipped out for a busy following day. Life of an entrepreneur: not interested or uninterested, or rather just not interested enough…unsure why, the physical attraction was on point but he seemed young with big dreams, like me but different -- foreign born with wild stories of success, failure, silicon valley, losing himself and otherwise - common ground of self definition + free spirited elegance — could be fun, but not forever.

A week later we rendezvoused at a birthday on the LES, late. Now, if im going out, late, i have a mission in mind, hunting no doubt. thirsty. The Live DJ was dropping beats and i was dropping low. I danced my face off, and he arrived. im not typically DTF, until i am - and my two cocktail cap either leaves me face planting or in it to win it and after seven months of celibacy post breakup, it was game on because you’re either driving or driven, so i took charge + took him home - to his place. I keep mine for me, so i can hit the eject button at my discretion.

His barely lived in soho loft had no furniture— just empty moving boxes as end tables, charcoal for drawing, a jar of half eaten macadamia nuts, and a bed in the back. I urged myself to behave but sometimes your body just decides for you. So i took the thinking out of it and allowed myself to feel. we quickly consummated our initial crosby street conversation on his wood floor - wild in the most tame way possible --- “two” much tequila, with a foreigner, ripped tights, and maybe some minor bruises from the unfinished flooring of his unfurnished loft. But What a guy! He even brought me water and tucked me in before i closed my eyes for a few hours. And just before sunrise, i awoke to look out the windows over broadway, soho lights + the city i love and smiled with great success. My thirst was quenched, appetizer satiated and my Feminism revived, validating yet, again that we are all animals. I took his charcoal crayons and signed my initials enclosed in a heart on an empty box in the living room, And left.

Brad, an old soul, with overwhelming confidence, sex appeal, and refined swagger. He made me feel alive after 7 months of celibacy and a year prior of a sexually deprived relationship. I would have totally hollered again when i got hungry but soon after leaving his loft, i learned he was so. much. younger. I have unabashedly avoided him since. As mentioned, I am not really DTF, unless i am, but i prefer aged meat to fresh meat and will leave the cougaring to the Real Housewives.

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