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November 12, 2022
Bradenton, FL
#RachelWonTheJackPot

Rachel & Jack

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Jack Pogan

and

Rachel Fleishman

#RachelWonTheJackPot

November 12, 2022

Bradenton, FL

The Beginning

How Pocahontas met Ace Ventura

In the summer of 2013 Jack and Rachel both started college at UCF and were constantly around each other- but didn’t even know it. In hindsight, they discovered that each semester they had at UCF, they both lived in the SAME building on and off campus until they graduated… great minds think alike. When Jack lived in his first summer Hercules dorm at UCF, Rachel was right across the courtyard in the Nike dorm. That Fall semester, Jack and Rachel both moved to the Neptune dorm and were in buildings adjacent to one another. In the last year they spent on campus they both lived on the same floor, of the same Hercules building, but STILL didn’t meet in person. Jack claims he saw Rachel once or twice in the elevator but couldn’t find the words to introduce himself. It wasn’t until the summer of 2016 at a local college bar, The Knights Library, where they first were introduced by our friend Tal Harel. However, it was just a quick hello because Rachel had a boyfriend at the time (scandalous). Jack never forgot her and found her so gorgeous. In October 2016, Tal invited Jack to a sorority date function in November, where she was going to pair him with another friend of hers. Jack, remembering Rachel from a couple months back, asked Tal if Rachel was going with anyone and Tal said “say no more”. Within 10 minutes, Tal made the connection and Rachel and Jack started to text. From the countless corny dad jokes to the deep conversations, they really connected and couldn’t stop talking to one another. Even to this day, they haven’t seemed to run out of words to one another. Before the date function, they decided to go to a Halloween party together to break the ice and officially meet in person. Rachel dressed up as Pocahontas, to which Jack coined “poca-hotness”, and Jack went as Ace Ventura, Pet Detective. They felt like the only two people at the party and were inseparable. Needless to say, the rest is history.

Their Life

A Comedian and a Lawyer Walk Into a Bar

After a month of officially dating, these love birds said “I love you” at Rachel’s UCF Graduation party. They had a few more months together in person before Jack decided to pursue his dream in comedy and entertainment in Chicago. While Rachel pursued a law degree from Barry University in Orlando, Jack was practicing Comedy at Second City in Chicago. Little did they know that they would be apart for 3 years in a long-distance relationship. The experience only strengthened their relationship as they treated every monthly reunion as a “mini-vacation”. Rachel would visit Chicago to see Jack and her hometown best friends frequently- no matter the weather. Rachel always had the intention to move up there once she completed law school because her man, her people and a big city were all there waiting for her. In March of 2020, COVID-19 hit, and Jack temporarily moved back to Florida while Rachel received her law degree shortly after. In the middle months of 2020, Rachel studied tirelessly to pass both Florida and Illinois Bar Exams, and the couple prepared to make the move back to Chicago. On July 31st, the day before moving to Chicago together, Jack asked Rachel to marry him. He planned the perfect proposal- he asked her whole family to be there to surprise her and proposed with a ring that combined her mother’s diamonds and Jack’s great-grandmothers diamonds. After celebrating that night, they woke up the next morning to drive 17 hours in a minivan to their new home, downtown Chicago. Rachel and Jack spent their first year in Chicago living together for the first time and enjoying the engaged life. They both landed awesome jobs and had incredible city adventures. In October of 2021, they made the decision to not only move back to Florida to be closer to family, but to better situate themselves to begin planting their own roots. Currently, they reside in Tampa, Florida and look forward to making new memories with friends and family before their wedding in November.

For all the days along the way
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