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Cayley Madison Boire

Executive Matchmaker

Cayley Madison Boire

Before you proceed reading about me, it's imperative that you know I, first and foremost, value honesty and transparency. My journey has not been perfect, yet I made it to where I am today: a place where I never feel my work is work. Maybe my number of passions is excessive, or maybe - just maybe - they are allowing me to live my best life.


My path was so perfectly calculated until March of 2020. I planned to get my degree in pastry arts, attend business school, learn how to be a great leader from some of the best in the industry, and open my own business. However, the pandemic certainly allowed me to do some reevaluation of my life. In my experience leading hospitality teams, I realized that my favorite elements of my day to day were when I was able to coach, encourage, and understand my coworkers on a deeper level so that we could perform to the best of our abilities. Additionally, I loved execute proposals and weddings (who doesn't love a great reason to celebrate?!). Despite what it may seem, between these experiences and studying psychology in college and independently (admittedly, I am a little bit of a nerd) - my transition to becoming a matchmaker was natural.

As an executive matchmaker for Tawkify, I work with successful individuals that opt to outsource their dating lives and avoid the clutter and time involved in online dating. My clients trust me and my team to genuinely dive into learning about who they are, both personally and professionally, and introduce them to compatible matches. My hope is to be a catalyst for healthy, long lasting relationships. In addition to our own private database, I utilize executive recruiting strategies to find exceptional people who are compatible with our clients. Once we find a match, we curate fun, unique dates that allow our matches to see why we felt there was great potential for a connection! I’ve felt immense joy from bringing many incredible people together that wouldn’t have met otherwise.

If you have a desire to outsource your dating life, we offer both paid and free experiences - feel free to email me directly if you or a friend are interested in being involved in dating in this way. I'd love to help you on your path to finding your person!


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