About | The Hitchmen Matchmaking

About Jason

Jason Robert Gaylord

Founder & CEO · Certified Matchmaker & Dating Coach

Jason Robert Gaylord is a certified matchmaker, dating coach, relationship expert, creative director, model, and athlete. He is the CEO and founder of The Hitchmen, and his purpose in life is to help people find true love, connection, and community. Jason has appeared in multiple magazines, on television networks, and across other major media outlets, and is one of the most sought-after, private, and successful matchmakers in the industry, working with both men and women of all ages and sexual orientations. He graduated from Old Dominion University in Norfolk, VA.

Now based between NYC, Los Angeles, and Florida, Jason's background in matchmaking, soccer, and fashion has allowed him to live on three different continents and build a global network and client base across North and South America, Europe, the Middle East, Africa, and Asia.

As a former D1 and professional soccer player, he values the importance of self-confidence and personal growth. "I believe that by empowering individuals to continue working towards becoming the best version of themselves, they can attract the community and love they desire. It is the idea of look good, feel good, date even better."

Jason was born in Kendall, NY, to Dawn and Robert Gaylord. He has two older sisters, Kristina Nesbitt and Sarah Collyer, along with two nieces and three nephews whom he loves with all his heart. If you have ever met him, he always says that one of the main reasons he started The Hitchmen was with the intention to help people find love like his grandparents shared for 71 years of marriage.

"My grandmother, Diane Furness, is one of the main reasons why I started The Hitchmen Matchmaking. She is a devoted wife, mother, grandmother, great-grandmother, fashionista, best friend, but above all, the kindest and most caring person I have ever met. A woman who started bringing me to nursing homes and hospitals when I was as young as 5 years old to visit sick and elderly people who needed some love and friendly smiles. She taught me love, compassion, kindness, and the importance of taking the time to bring love and joy to others. I am rooted in the love and values of my family, my own meaningful relationship, and my purpose as your matchmaker and wingman to guide you toward your perfect match. Let's get to work."
Sincerely, Jason at The Hitchmen

About Shannon

Shannon

Matchmaker

Shannon is a natural connector and brings a unique combination of discernment, global perspective, and pattern recognition to modern matchmaking. With a background in law and executive coaching, she is an expert at assessing nuance and identifying alignment quickly.

She's lived across Paris, LA, Miami, Tel Aviv, and NYC, and developed a strong instinct for recognizing alignment, often before others see it themselves. She has consistently observed that self-aware individuals aren't lacking options; they're lacking clarity on what actually makes a relationship work.

Her work focuses on identifying those gaps and blind spots, where attraction, timing, or perception can obscure true compatibility. She draws on a deep study of psychology, human design, and attachment theory to understand not just who someone is, but what they actually need in a partner and why past patterns haven't worked.

The goal is not more options. It's aligning on the right fit.

Shannon works with a highly curated group of clients who are done with surface-level dating and ready for something intentional. Known for her candor, precision, and ability to hold both the emotional and practical dimensions of compatibility, she creates matches that are selective, deeply considered, and built to last.

About Chelsea

Chelsea Volpe

Dating & Image Coach · Fashion Stylist

Chelsea Volpe is a New York City-based dating and image coach, fashion stylist, and creative director with more than a decade of experience helping people present their most authentic, confident, and compelling selves. A Fashion Scholarship Fund Scholar and industry veteran, Chelsea has worked with global brands including Louis Vuitton, Chanel, Prada, Dior, Netflix, Disney, Amazon, and Porsche, building a career around understanding human behavior, first impressions, personal branding, and the psychology of attraction.

Known for her direct yet empathetic approach, Chelsea helps clients bridge the gap between who they are and how they are perceived. Her coaching focuses on confidence, communication, dating strategy, self-presentation, style, and emotional intelligence, helping men attract meaningful relationships without relying on gimmicks, scripts, or inauthentic tactics.

Drawing from years spent working with executives, celebrities, entrepreneurs, and creatives, Chelsea understands that attraction is about far more than appearance. She helps clients develop presence, social confidence, conversational skills, personal style, and the mindset necessary to build genuine connections. Her philosophy is simple: the most attractive version of you is the most authentic version of you.

Whether reviewing dating profiles, refining a client's wardrobe, preparing for first dates, or helping someone navigate modern dating challenges, Chelsea combines practical advice with honest feedback and actionable strategies that create lasting results.

"I am dedicated to helping people become the most confident version of themselves, both professionally and personally."

The people in your corner.

Jason Robert Gaylord

Shannon

Chelsea Volpe

Ready when you are.