Deep Conversations Drive This Matchmaker’s Careful Process

The Short Version: A great matchmaker will treat your love story with the care it deserves. Matchmaker, dating coach, and The Match Pro founder Kimberly Simonetti spoke with us about introductions, detailed questionnaires, and what sets a high-quality matchmaking service apart.

Anyone who has tried to catch someone up on their love life knows how much ground there is to cover. Recently I was out to dinner with my closest friends and a friend I’d chatted with now and then. We were talking about a situationship I’ve been caught up in over the past few months.

While I caught my close friends up on the latest developments and juicy bits of drama, it hit me how much backstory and context the newer friend was missing, since they hadn’t been around for the play-by-play as it unfolded.

I also discovered I wasn’t quite the relationship historian I’d believed I was. My other friends kept fixing little details as I told it, and after thinking it over, I saw that they remembered things a little more accurately.

Putting what’s going on in your heart and mind into words for other people can be a lot to ask, but it matters. Talking things out can soothe some of the painful feelings relationships bring up, and it can also help you get clear on what you do and don’t want.

Kimberly walked us through how matchmaking works.

Few parts of the matchmaking process matter more than your story. Look for a matchmaker who doesn’t just care about that story but wants to play a part in it.

Kimberly Simonetti is a matchmaker, a dating coach, and the founder of The Match Pro. She launched the matchmaking service in 2015 so that people ready for a lasting relationship could meet someone and fall in love.

She told us how she discovered her love of matchmaking and why her process centers on your story, and she shared some advice for coping when dating starts to wear you out.

“I’m a super connector,” Kimberly said. “I connect everybody and everything. When I discovered matchmaking, it felt like the natural shift for me. Before I was even a matchmaker, I organically connected people who are still married today.”

Kimberly Zeroes In on What Counts Most

Before she was making matches, Kimberly was a professional photographer. According to her, once online dating began popping up in the late ‘90s, people started coming to her for a somewhat different reason.

“People had come to me for photos for matchmakers, local papers, and magazines,” Kimberly said. “Singles were looking for each other through the kind of old-fashioned ways. But then, in late 1998 and 1999, I started getting calls from some of my clients who wanted photos for this new thing.”

Since the ’90s, Kimberly has been helping singles succeed at dating.

The “new thing” in question was Match.com, and some of Match’s very first users were Kimberly’s clients. They came to her for profile photos, and even though online dating was brand new, she knew photos had to rank among the most important parts of a dating profile.

“Digital photography was in its infancy at this point,” Kimberly explained. “My clients were finding success with their photos, and getting dates.” 

Kimberly grasped right away how much photos matter in online dating, which is still true today, and she developed a style that gave her clients natural yet high-quality photos. Moving into matchmaking in 2015 felt like a natural step, she told us.

Photographers tend to bring out the most striking features of the people they shoot. In a lot of ways, matchmakers do the same.

Kimberly kicks off the matchmaking process with a thorough interview, drawing out the key parts of your background and your relationship goals without overlooking the important things that can be harder to talk about.

Knowing Yourself = A Better Dating Life

“I have a very in-depth conversation with my clients right before I take them on,” Kimberly said. “That means I’m very selective about who I take. It’s not about getting all the clients I can– it’s about finding success for the clients I do find.”

A large database says good things about a matchmaker, though it isn’t the sole predictor of success. You want a matchmaker who’s eager to know you as a person. This is who’ll be arranging your dates, after all. You’re gonna want someone who gets you.

In that first interview, Kimberly asks every client whether they’re ready to give what they’re looking for. “You need to make sure, first things first, are you what you’re asking for?” she said. “So you may say, I want someone with a college degree, who makes seven figures, this, that, or whatever.”

When clients share their lists of must-haves, Kimberly nudges them to consider what they themselves have to offer. She said this helps them calibrate their expectations and see the dating process more clearly.

In those first interviews, Kimberly helps clients figure out whether matchmaking is the right step for them.

The goal is to make sure you start the process with realistic expectations and, just as important, an open mind.

The first interview lets Kimberly get to know you, and it also helps her judge whether matchmaking is the right route. Matchmaking is designed for serious daters, people prepared for a mature, committed relationship. And that kind of relationship takes more than simply wanting one.

That’s especially true in the early stages. According to Kimberly, the ideal matchmaking client comes with an open heart and an open mind. Once your profile is in, you’ve spoken with Kimberly, and you’re sure The Match Pro is a good fit, you can pick from several membership options.

Kimberly and her team guide clients to the membership that fits their goals. With your membership in place, the best part of matchmaking starts: the introductions.

You get to enjoy the fun parts of date night, like choosing the perfect outfit, and leave the logistics to your matchmaking team.

You’ll check in with Kimberly after every date. She wants to hear all about it, from your first reaction on seeing your date to how the conversation flowed over the course of the night.

If you two click and the interest is mutual, she’ll help you get back in touch. If the date didn’t do it for you, Kimberly takes notes so your next introduction is an even better fit.

“I always survey both people after a date,” Kimberly said. “I find out if there was eye contact, if the conversation flowed naturally, and where there were areas for growth and improvement. We’re all works in progress, and sometimes small tweaks can make dating much better.”

Keep It Real: Love Is Out There

Serious daters are who matchmaking is for, but what does being a serious dater actually mean? And how can matchmakers be sure only serious daters end up as clients and in their databases? For Kimberly, it all hinges on that first interview.

“One of the questions I ask early in my interviews with potential clients is: ‘On a scale of one to 10, what’s your level of interest in really finding someone?’ One is you don’t care if you find that person or not, and 10 is you can’t think or breathe until you find that person,” Kimberly explained.

Kimberly said matchmaking isn’t a way she can help people who rank low on that scale. In her view, matchmaking works best and is most enjoyable when clients are committed to finding love.

Matchmaking is serious business, and Kimberly doesn’t want people who aren’t serious disrupting it.

When you’re just focused on living your life, you never know who you might meet.

“I need somebody who’s really hungry and interested, and ready to move in that direction,” Kimberly said. “Not being serious about a relationship while matchmaking is kind of like showing up to an all-you-can-eat buffet and you’ve already eaten.”

Clients who aren’t ready for matchmaking still get wisdom and direction from Kimberly. At times she passes along books and articles written by experts in dating and relationships. She’ll also point them toward podcasts and coaching programs suited to their particular circumstances.

“I always tell people to do one thing– join Meetup, and get out and do something they’ve wanted to do but haven’t yet,” Kimberly said. “It might be pickleball, it might be hiking– it can be anything as long as you go someplace new and see if you could organically find your person.”

Whether she’s coaching or matchmaking, Kimberly’s goal is to help you help yourself. Matchmakers make dating simpler, but they can’t conjure up your perfect partner. You have to do your part, too.

“I think there’s somebody out there for everybody,” Kimberly said. “It’s just a matter of how and when, and sometimes we just need to hone our approach to find that, whatever it is.”