How Jeff Went from Overwhelmed to Exclusive – The Power of Doing Dating Right
If you’re a smart, successful, and (let’s be honest) a little frustrated with modern dating, you’re not alone. My client Jeff—mid-60s, business professional, father, grandfather, art lover—was in the exact same spot before he worked with us at Match Me Canada.
Jeff was juggling traditional matchmaking and online dating, trying to figure out what actually worked. He wanted to meet someone, but the idea of endless swiping and awkward messaging? Not his thing. That’s where we came in.
We took over. We messaged. We filtered. We coached. Jeff got to skip the exhausting parts and just focus on meeting incredible women. And guess what? He’s now in an exclusive relationship.
So, what was it like having a team manage his dating life? Let’s hear it from Jeff himself.
Read on for our full Q&A!
Q&A: Jeff’s Online Dating Experience with Match Me Canada
Rebecca Cooper Traynor (RCT): So, Jeff—you’ve been working with us for a few months now. What’s it been like having a team behind your dating life?
Jeff: Honestly? It’s been a game-changer. I never thought I’d have a dating team, but here we are! Before, online dating felt like trying to assemble IKEA furniture without instructions—lots of effort, very little progress. But with you running the show, suddenly, it made sense. I had better matches, smoother conversations, and way less stress.
RCT: I mean, who doesn’t want a dating concierge? What was the most unexpected part of the process?
Jeff: I was not expecting to enjoy it this much. I thought online dating was going to feel like a chore, but you actually made it… fun? You handled the search, the initial messaging, even helped me refine how I communicated. Instead of endlessly swiping and guessing what to say, I just focused on meeting great women and having real conversations. And let’s be honest—that’s the part that actually matters.
RCT: We love that! Let’s talk about the messaging—what was it like letting us handle that part for you?
Jeff: Oh, it was a relief. Look, I’m great at business communication, but flirty text banter? Not exactly in my wheelhouse. Your team knew how to start engaging conversations that actually led somewhere—no small talk that fizzled out, no awkward exchanges. Just real, interesting conversations with women I actually wanted to meet.
RCT: And then there’s the dreaded first date. Did having us in your corner change how you approached those?
Jeff: 100%. First dates used to feel like interviews—stiff, repetitive, and exhausting. But after your coaching, I started enjoying them. You gave me better conversation starters, helped me get comfortable sharing more about myself, and reminded me that it’s supposed to be fun. By the time I was meeting these women, I already felt like we had something to talk about, which took all the pressure off.
RCT: And let’s not forget—you’re now seeing someone exclusively! How does it feel?
Jeff: Exciting. I never expected to meet someone this quickly, but that’s the beauty of this process—it actually works. You helped me connect with someone I might have overlooked on my own, and now I’m in a relationship I feel really good about. That’s the goal, right?
RCT: Exactly! Now, be honest—how often did you second-guess my team’s advice?
Jeff: (Laughs) I mean, I tried! But every time I thought, “That won’t work,” it actually did. Like when you told me to keep my profile focused on what makes me unique instead of writing what I thought women wanted to hear? That got me way more interest. Or when you told me to let go of perfect timing and just go for the second date? That’s how I met the person I’m dating now.
RCT: So what would you say to another professional, mid-60s guy who’s skeptical about letting a team take over his dating life?
Jeff: I’d say, “How much time do you want to waste before you meet someone great?” Because I spent a couple of years trying to figure this out myself, and in just a few months with you, I met someone I’m really excited about. If you’re serious about finding a meaningful relationship, let the experts do what they do best.
RCT: Jeff, it’s been such a pleasure working with you. Any final thoughts?
Jeff: Just a big thank you. I came into this hoping to meet someone, and I ended up with so much more—a great experience, a new perspective on dating, and ultimately, a relationship I’m really excited about.
Jeff’s story is exactly why I do what I do. If you’re serious about finding a meaningful relationship, let’s stop guessing and start doing this right.
👉 Book a call with me at Match Me Canada, and let’s find your person.
