About The Real Matchmaker

At The Real Matchmaker, we act as your socially savvy personal dating coach and recruiter to network through a variety of channels to actively scout personalized, quality dates just for you. We take pride in drawing attractive, successful professionals into our single social network so that your dating life is transformed seamlessly.


Jessie Kay


I have been a Director/Matchmaker for over 22 wonderful years. My venture into dating services began with Great Expectations, the largest and oldest dating agency in the nation. I believed at the start, as I do today, that helping others find love is my calling and my passion.

"Finding someone you’re attracted to doesn’t have to feel like an exhausting part-time job anymore. I can't wait for you to fall in love with someone who wants to make a REAL connection."

- Jessie Kay
The Real Matchmaker

Matchmaking Services

I am “The Real Matchmaker” – a relationship and dating coach, a soulmate scout, a confidant, and a friend for my clients. All of this comes together to help you find your ideal companion and partner.

I make Real connections and Real sparks possible!



See how Jessie’s matchmaking approach results in success

Matchmaking Blog

Dating tips, relationship advice, and more from a professional matchmaker
Dating Expert for Men

Contact Jessie

Get in touch with the dating coach and start your journey toward finding love
Connect with Your Matchmaker
Tell Me All About Yourself

Thank you for your interest in The Real Matchmaker! I look forward to getting to know you and helping you find the love of your life. To get started, complete this short form and I will contact you about beginning our journey.

  • First and Last Name
  • Email Address
  • Phone Number

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