Donna Farizan Talks About Her Experience with a Matchmaking Service

I’ve spent the last five years single. In the initial years, I didn’t prioritize dating; I focused on my healing journey. This wasn’t just about getting over a single breakup but involved navigating the collective heartbreak and disappointments that romance can bring.

I engaged in workouts aimed at releasing emotional blocks in my body, practiced meditation, attended workshops on emotional understanding, went to therapy, and consumed numerous self-help books and podcasts. My objective was to concentrate on myself and address any insecurities or traumas stemming from past failed relationships. However, introspection only goes so far. Eventually, I knew I would need to re-enter the dating scene. Ironically, I realized I was ready to take dating seriously when I found myself completely content being single. I am happier than ever on my own and finally comfortable in my skin. After all, as the saying goes: you must love yourself first before you can truly love someone else.

And so began my dating journey.

In recent years, I’ve explored dating apps, setups, speed dating, and even ventured out to flirt in real life! This time around, I really committed to finding my match. In my teens and twenties, I focused more on advancing my career than on dating. Now, at 33, I’m eager to invite more romantic love into my life.

With my heart and mind wide open, I decided to explore a method I found intriguing: modern matchmaking. My experience on dating apps had been underwhelming; after a few months, they started to feel like a game, as if the algorithms preferred to keep me searching rather than help me find success. Since I work for TODAY, our executive producer proposed that I try working with a matchmaker and document the journey on air. To my surprise, I quickly agreed without hesitation; I was curious about this untested method and hoped it might lead me to love.

Prominent outlets like The New York Times, Business Insider, the New York Post, and The Atlantic have reported on the resurgence of matchmaking, sparking interest and discussion among my single friends and me. Obviously, I turned to a professional: Devyn Simone, a matchmaker and dating expert from Three Day Rule, a modern matchmaking service.

Devyn gladly accepted my case. During our Zoom meeting, I shared what I was looking for: someone kind, driven, family-oriented, culturally open, and someone who possesses a growth mindset and a zest for life. The meeting felt somewhat like a date! She inquired about my life, both professional and personal. Then she encouraged me to use the same intentionality, consistency, and patience I applied to building my career to cultivate a meaningful relationship. Devyn also asked about my past relationships, what worked, and what fell short — which surprisingly felt easier than I expected.

Next, to help clarify my priorities, Devyn guided me in identifying my top three must-haves and dealbreakers, plus a wish list. She highlighted qualities I might need in a partner, such as someone with intellectual curiosity, emotional intelligence, and a sense of purpose. I was thrilled to converse with someone who not only understood my perspective but could also help me better define the attributes that mattered to me.

Months later, Devyn, her colleague Krissy, and I met again to review our previous discussions and delve into my two upcoming matches — just moments before my dates with them. (We arranged it this way for the efficiency of documenting the process for the show, but typically clients make contact with their matches within 24-48 hours.) Unlike certain matchmakers, Devyn believes in showing clients photos of their matches beforehand so there are no surprises, and we adhered to this approach! Upon seeing photos and bios of the two gentlemen I was about to meet, a rush of excitement, nerves, and adrenaline surged through me.

Let’s do this, I thought to myself.

I was accompanied by Devyn, Krissy, my producers, and our camera crew, ready for my first date, which was set at a billiards venue. (Devyn’s tip: activity-based dates are excellent because they alleviate the pressure of constant conversation and yield more organic interactions — far more comfortable than sitting rigidly at a bar.) Just ten minutes before the date was supposed to start, I stepped into the restroom to change into my billiards outfit. Upon re-entering the room, I heard a male voice on speakerphone — it was my date, calling the matchmakers to inform them he could no longer make it. The room buzzed with justifications for his absence, extending him the benefit of the doubt, yet my intuition sensed: this was a guy who could have managed to come if he really wanted, but instead, he stood me up.

And what I came to realize? Dating within matchmaking mirrors the dating experience in the broader world, even in a situation as organized as mine — with two producers managing logistics and filming the date, plus two matchmakers evaluating and securing the connections — things can still go awry. Ultimately, you can’t evade the challenges and pitfalls of dating. Instead, one must build the resilience to face them and remain steadfast until the right partner arrives.

My date with my second and final match took place immediately afterward. I changed into another outfit for bowling (another activity-based alert!) and, feeling slightly disheartened, I regrouped my energy to offer this guy my full attention. He was kind, respectful, and fun to be around. Though my matchmaking journey was limited, I hope it continues because, despite not finding the one, I felt a significant internal shift — a gateway of new possibilities opening up. While I can’t say my matchmaking experience (so far — now that I’m in their database, there’s always a chance for future matches) was any better than what I experienced on dating apps, I did learn a great deal about myself. Working with Devyn has enabled me to clearly express what I seek and what I wish to avoid in a relationship, marking progress in the right direction.