The Real Matchmaker™ Jessie Kay Takes the Stress Out of Finding Love With Her Matching Services

The Short Version: Busy professionals often lack the time to go on date after date looking for the perfect partner. That’s where The Real Matchmaker Jessie Kay comes in to help them cut through the quantity and find quality matches. She and her small team of dedicated matchmakers teach men and women in metropolitan areas around the world how to find love. The Real Matchmaker offers a concierge experience, and Jessie gets to know each client to understand their desires and show them how to present their best selves to prospective dates.

“I thought I would be alone forever.”

That’s a line from a lovely letter that Jessie Kay, The Real Matchmaker, received from an ecstatic client who is moving in with a guy who Jessie picked out for her. The lucky lady, Madison, said she’s in a great relationship with a compatible partner for the first time. They have great conversations about their passions, participate in activities they enjoy, and make plans for the future.

Jessie helps busy professionals meet their ideal match.

“I don’t think I’ve ever felt so completely happy with somebody before,” said Madison. Hers is just one of the many success stories that Jessie has heard from satisfied clients.

Jessie is effective as a matchmaker because of the communication skills she learned growing up. She was adopted and didn’t naturally share race, skin color, or style with the other members of her family. But she learned how to fit in with her family so she didn’t feel left out, socially. Eventually, she developed empathy for those who tried hard but couldn’t fit in.

As Jessie approached adulthood, she became proficient in making herself likable. “Once I realized my power and energy, I became one of the most popular people in my graduating class,” she said. Because she was proficient in making herself — and others — likable, Jessie chose a career path where likeability and helping others were two significant parts of the job.

Jessie got her start more than two decades ago with Great Expectations, the nation’s oldest and largest dating agency. She then set out on her own, founding The Real Matchmaker to work closer with her clients to help them find love.

Jessie works one-on-one with clients to connect with them personally and to better identify the right person with whom to match them.

“I hold my clients’ hands through one-on-one matchmaking, and I pride myself on actually working for them,” she said.

Because of the time-intensive nature of her work, Jessie limits intake of new clients to just three or four a month. “It’s important that we have a real relationship — or even friendship — so that finding love for them becomes more organic, she said.”

She has two team members who assist her by scouting dates. The pair is a bubbly duo who work tirelessly meeting people and compiling information about their interests, so they can make the most suitable matches.

Jessie loves matching her clients with someone who is likely to become a long-term partner, and she said forming friendships with her clients is one of the most rewarding parts of their journey together. As she brings on each new client, she listens to their stories of past successes and failures in romantic relationships. Then they discuss how the person has changed and grown throughout their journey in love, and what they’re currently looking for in a partner.

Watch on

As a part of her service, Jessie also helps each person look and feel their best with a makeover and photo session. She wants all of her clients to have attractive photos that will accompany the other information potential matches receive.

In addition to helping them look beautiful or handsome on the outside, Jessie helps clients learn to show their inner beauty through coaching, deep conversations, and role-playing. These exercises help them build the confidence they need to make a great first impression and experience fewer pre-date jitters that often creep up.

Jessie’s Dinner Date For Eight parties provide clients an opportunity to refine and sharpen their social skills — as well as the chance to meet someone. The dates are held at trendy restaurants around Los Angeles and Orange County, and each includes four women and four men. Diners are hand-picked by Jessie to ensure that a great vibe is present at the meal and that the conversation never lulls.

Jessie works with attractive and successful singles in major metropolitan cities, including New York, Los Angeles, Chicago, San Francisco, and Washington, DC. She also has international clients in locations like France and Spain.

Jessie has been a part of 73 engagements as a matchmaker, which she recently celebrated in an Instagram post.

Over the years of working with clients, Jessie has earned many positive online reviews, including a stellar rating on Yelp, where clients detail the benefits they’ve seen from working with Jessie. Many praise her intuitive ability to match people, her friendliness, and her focus on bringing out the positivity in people.

Jessie is active on social media, too, where she shares practical tips for dating and life. She engages followers on both Facebook and Instagram.

One recent post congratulated a pair of her clients who got engaged, and when they tie the knot, the happy couple will be the 73rd marriage for The Real Matchmaker.

Jessie is developing seminars for singles to expand the scope of her matchmaking service, and help both current and potential clients. She described them as “How am I doing?” seminars and said they will allow singles to see which areas they excel in — and which parts of dating with which they may need help.

The seminar will relate to their experience as a single person in the dating world, and participants will receive feedback from a panel of people of the opposite gender.

“I can’t tell you how much good energy and satisfaction I receive from each person I work with.” Jessie Kay, The Real Matchmaker

“The goal is for attendees to use the feedback to become the best they can be at enticing and attracting the mate they want,” she said. She added that she believes this method will lead to greater success for singles as they search for love.

The journey to finding love is not always clear-cut or easy, but Jessie believes it’s the only one in life which really matters.

“I can’t tell you how much good energy and satisfaction I receive from each person I work with,” she said.