I’ve been single for five years. The first few, I wasn’t focused on dating — I was on my healing journey. Not just from a single bad breakup, but from the collective heartbreak and disappointment romance can bring.
I did workouts designed to release emotional pits in the body, meditated, took workshops on understanding emotions, went to therapy, and yes, consumed self-help books and podcasts. My goal was to focus on myself and heal any insecurities and trauma I had from failed romances in the past. But, introspection can only go so far. Eventually, I’d need to get back out there. Funny enough, I knew it was time to commit to dating seriously because I was completely content being single. I feel happier than ever on my own, and I am finally comfortable in my own skin. You know what they say: You have to love yourself first before you can love someone else.
Enter in: my dating era.
For the past couple of years I’ve dabbled in dating apps, set-ups, speed dating and even just going out to flirt IRL! I really put myself out there with the intention of finding my match, maybe for the first time ever. In my teens and 20s I was focused on building my career, not dating. Now, at 33, my interest is revving up and I am ready to fill my life with more romantic love.
With my mind and heart as open as ever, I decided to try a method I was curious about: modern matchmaking. I hadn’t been getting dates on the apps beyond the first few months; they were starting to feel gamified, and as if the algorithm wanted me to stay on and keep searching, rather than find success and get off. Since I work for TODAY, our executive producer asked me if I would ever try working with a matchmaker and document the process on air. I surprised myself by saying yes without hesitation. It was a method I’d never tried and had been curious about, but mainly I agreed because I thought it might actually provide a shot at finding love.
The New York Times, Business Insider, the New York Post and The Atlantic have all reported on the rise of matchmaking, sparking curiosity and conversation among my single friends and me. Who better to turn to than Devyn Simone, a matchmaker and dating expert with Three Day Rule, a modern matchmaking service.
She happily took on my case. We got on a Zoom meeting and I told her what I was looking for: someone who’s consistently kind, driven, family-oriented, open to other cultures, and who has a growth mindset and a zest for life. Our meeting itself felt a little like a date! She asked me about myself, my work life and personal life. Then she requested that I use the same “intentionality, consistency and patience” that I had in designing my dream career to design a relationship that works for me. She also asked about past relationships, what worked and what didn’t — which, by the way, felt much easier than I had anticipated.
Then, to better organize my priorities, Devyn asked me about my three must-haves and three dealbreakers, as well as a nice-to-have list, all the while prescribing me with what I might need — i.e., someone who values intellectual curiosity, is emotionally intelligent and purpose-driven. I was so excited to speak to someone who not only understood where I was coming from, but who could also better identify and articulate the attributes that are important to me.
Months later, Devyn, her colleague Krissy and I met to recap what we had discussed in the past and to learn about my two matches — mere minutes before my dates with them. (We did it this way to efficiently document the process for the show, but typically people will be asked to make contact with their matches within 24-48 hours of being presented with them.) Unlike some matchmakers, Devyn believes in showing her clients photos of their matches before their dates (rather than going in blindly), and we did just that! I saw photos and bios of the two guys I was about to go on dates with, and I immediately felt a wave of excitement, nerves and adrenaline flow through my body.
Let’s do this, I thought.
I was with Devyn, Krissy, my producers and our camera crew, ready to roll on our first date, which was to play billiards. (Pro tip from Devyn: Activity-based dates are the best because they reduce the pressure of constant conversation and make interactions feel more organic and less forced — way more comfortable than sitting interview-style at a bar.) Ten minutes before the date was supposed to start, I went to the bathroom to change into my billiards outfit, and when I entered back in the room with everyone, I heard a male voice on speakerphone — it was my date, and he was calling the matchmakers to say he could no longer make it. The room bustled with excuses for his behavior, giving him the benefit of the doubt, but my gut knew: This was a guy who could’ve made it work if he really wanted to, and instead, stood me up.
And you know what I realized? Dating in the matchmaking world is just like dating in the real world on your own. Even with a situation as controlled as mine — I had two producers working on logistics and shooting the date, and two matchmakers vetting and securing the matches — things still didn’t work out. My point is, you can’t escape the flaws and perils of dating. Instead, you have to become strong enough to weather them and stay standing tall for when the right one comes along.
My date with my second and final match happened immediately after. I changed into my next outfit to go bowling (again, activity alert!), and since I was feeling a little disappointed, I regrouped my energy to give this guy as much as I could. He was kind and respectful, and easy to have fun with. My matchmaking experience was limited but will hopefully be ongoing, because even though I didn’t get matched with the one, I did feel an internal shift — a portal of new possibilities opening up. Though I can’t say my matchmaking experience (so far — now that I’m in the database, I could always get matched with someone else later on) was any more positive than a dating app experience, I did learn a lot about myself. Through working with Devyn, I’m now able to better articulate what I want and what I don’t want in a relationship, which is a step in the right direction.
I did learn a lot about myself. I’m now able to better articulate what I want and what I don’t want in a relationship, which is a step in the right direction.
