It was the week of Christmas, a notoriously bustling time for singles everywhere. Many are either ending relationships, settling in for “cuffing season,” or on the hunt to ensure they have a significant other to welcome the New Year. For matchmakers, this is akin to our tax season—we’re busy helping clients with their New Year’s resolutions, networking at local events, and gearing up for the year ahead by lining up dates for our clients. It’s essential for us to scout the quality of men that our clients desire.
Searching for High-Achieving Partners – The Matchmaker’s Perspective
Professional women in their thirties are typically searching for partners who are equally or more impressive in terms of education, career, net worth, and lifestyle. This means I’m often on the lookout for eligible men who may not be active online or frequent bars as they’re busy pursuing their ambitions. At the time, I was a 34-year-old single woman working with clients around my age—my experiences with the dating scene gave me a unique perspective. One of my clients was specifically seeking a hardworking, tall, dark, and handsome man with an MBA, which I found to be a straightforward task.
While searching for the right match for this client, I encountered countless men who fit the criteria. Some were actively dating, while others were in complicated situations or hesitant about the matchmaking process. One particular gentleman stood out to me. He was tall, had salt-and-pepper hair reminiscent of George Clooney, and was in his mid-thirties, never married, and held an MBA while serving as a managing partner at an insurance agency. I approached him, hoping to spark his interest in my client. I said, “Hi there, I know this is random, but I’m a VIP matchmaker and think my client would be interested in you. I’d love to see if there’s a possible love connection.” Unfortunately, I was met with silence. He may have thought I was a scammer or, worse, someone solely after successful men’s money. I wished him well and moved on, forgetting about him for the following months.
As spring arrived, cuffing season had passed, but summer was on the horizon, and singles were eager to find beach vacation companions. As a matchmaker, I understand the challenges of dating. I often feel that I can read people’s energies within minutes, which sometimes leads me to dismiss potential connections too hastily. To combat this tendency, I decided to put myself back in the dating scene with a set of personal boundaries and guidelines. After all, many success stories often start with mediocre first dates.
I joined a dating app and began my swiping journey. I chatted with two guys for several days, only to be ghosted by both before meeting them. It was disappointing, but I refused to let it deter me. Then, I came across a profile of a striking man with salt-and-pepper hair and a professional demeanor. Intrigued, I liked him, and he liked me back. He suggested we go on a date, and I accepted. He offered options of bowling or Topgolf, and I chose Topgolf. We agreed on a date and time a couple of days later, then… silence. Until the day of the date, I was left wondering whether he would show. Thankfully, he confirmed just in time, and I hoped for the best.
First Date with My Future Husband: An Unexpected Reunion
The day arrived, and I walked into Topgolf to find my date, Pete. He was handsome, perhaps a bit nervous, but we grabbed our clubs and headed to our reserved spot. As a professional matchmaker, I know how to initiate conversation—though Pete seemed unsure. He asked me, “So, what do you do for work?” I laughed, suggesting he grab a drink first. We started with him sharing details about his business, which happened to be the same field my dad had worked in for 40 years. That was a conversation starter for me. When it was my turn, I told him, “My job is probably different from any other date you’ve had; I used to work in healthcare, but now I’m living my dream of being a matchmaker.”
The room fell quiet. Then, to my surprise, he exclaimed, “Wait… are you Kate O’Connor?” Stunned, I replied, “Yes! Have you seen me on the news?” He revealed that I had approached him months earlier while searching for a match for one of my clients and even showed me the contact details I had given him. I was taken aback; this was the first time I had ever encountered someone who remembered our previous interaction. What a small world!
We spent the next two hours at Topgolf, sharing laughs and genuinely connecting. As the date came to a close, I smiled and mentioned that I hoped to see him again. He said it was refreshing to hear a woman express her interest so openly. Little did I know that this man would become my husband; 1.5 years later, Pete proposed to me in Athens, Greece, with a stunning ocean view. We still chuckle about our first encounter, and I now realize that my matchmaking adventures had led me to find my soulmate.
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