Leopoldo & Jessica

Leopoldo & Jessica

May 19, 2025 • Cleveland, SC
33 Days To Go!
Leopoldo & Jessica

Leopoldo & Jessica

May 19, 2025 • Cleveland, SC
33 Days To Go!

Our Story

Never Say Never

Picture of Never Say Never

Jessica and Leo's paths crossed in 2019 through a mutual friend and business partner, Nick Bosley.

After a brief encounter and a quick handshake, Nick decided to play matchmaker. He asked both Jessica and Leo what they thought of each other.


Leo thought, “Who is that tall blonde?”


Jessica mused, “He’s cute, but he’s shorter than I like. I never date guys shorter than me.”


Nick relayed Jessica's thoughts to Leo, who smirked and thought, “Challenge accepted.”


From that moment on, Leo began to flirt with Jessica at the office. Initially, she mistook the ring on his finger for a wedding band, which annoyed her. However, when she noticed it was on his right hand, her irritation faded, replaced by blushes and a growing appreciation for his wit and playful nature.


Their initial spark blossomed into a solid friendship, filled with laughter and shared moments. Leo would often cook for Jessica, showcasing his grilling skills, while also revealing his musical talents.

When the world changed with the onset of COVID-19 in 2020, they chose to quarantine together. Instead of feeling confined, their time together deepened their connection. They explored each other's pasts, quirks, dreams, and ambitions, transforming their friendship into a profound love.


Jessica admired Leo's big heart; he frequently shared stories of his nieces and nephews and boasted about his brothers, Aaron and Charlie. She was drawn to his relentless pursuit of self-improvement—reading books, diving into YouTube rabbit holes, and seeking mastery in his profession. Leo's giving spirit shone through his thoughtful gestures, like creating goody bags for the homeless in winter and generously tipping service workers. His adventurous nature perfectly matched hers; together, they traveled from the stunning landscapes of the West to the vibrant cultures of Costa Rica, Mexico, and the Dominican Republic. He often surprised her with gifts and flowers, simply because.

But it was Leo's spiritual yearning that truly touched Jessica. His desire to grow closer to God and lead a life pleasing to the Lord gave her hope for a future rooted in faith. She envisioned a marriage built on a foundation of love and devotion, one strong enough to weather any storm life might throw their way.


From the very beginning, Leo saw Jessica for more than just her beauty. He was captivated by her intellect, independence, and sharp wit. She not only made him laugh but inspired him to be a better man. Her selflessness and dedication to helping others, even before achieving personal success, showcased a profound strength of character. Leo admired her positive outlook, especially when challenges arose, and he respected her leadership qualities and commitment to living in alignment with her values. As he watched her lead with compassion, he felt a longing to rekindle his own relationship with God.


Deeply in love, Leo took a significant step by introducing Jessica to his family in Texas in the Fall of 2021. The warmth and connection during their time together solidified his certainty—Jessica was the one he wanted to spend his life with.


Jess and Leo each moved to Nashville with their own aspirations and dreams, but life has taken unexpected turns since their arrival. Looking back, it's easy to see how our plans can diverge from God's greater purpose. He is the master creator, and it was His intention for this couple to forge a life together. While they thought Nashville would be a launchpad for their careers, it ultimately led them to one another. In the end, they learned that sometimes the best outcomes arise from the most unexpected paths—so never say never, because life has a way of surprising you when you least expect it.