In Depth Conversations Guide The Match Pro

Men's Dating

In-Depth Conversations Guide this Matchmaker’s Detailed Approach

Chloë Hylkema

Written by: Chloë Hylkema

Chloë Hylkema

Chloë Hylkema has covered hundreds of people, services, and ideas in the dating and lifestyle sphere, all explored through the lens of making dating enjoyable. She has earned her bachelor's degree in English from Emory University and worked on animal rights advocacy issues and research in the past. Chloë is passionate about delivering readers the information and resources they need to forge conscious and self-realized connections. When she’s not writing, you can find her cooking a vegan feast or at the climbing gym.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Reviewed by: Shanna Ellis

Shanna Ellis

Shanna Ellis, Managing Editor at DatingAdvice.com, has spent over a decade working at online publications as writer, editor, and director of content. The online brands under her leadership have seen coverage from Forbes, USA Today, and Insider. She holds a BA in Advertising and minor in Communication Studies from the University of Florida. Her role for DatingAdvice includes conducting insightful interviews with dating professionals, enriching readers with invaluable advice on dating culture and relationships.

Discuss This! Discuss This!

The Short Version: A great matchmaker is going to give your love story the attention it deserves. Kimberly Simonetti, a matchmaker, dating coach, and founder of The Match Pro, talked to us about introductions, in-depth questionnaires, and what makes for a high-quality matchmaking service.

If you’ve ever tried to fill someone in on your love life, you’ll know there’s a lot of ground to cover. I was just out at dinner with my closest friends, along with a friend I had chatted with here and there. We were discussing a situationship I’ve found myself in in the last few months.

As I was filling my close friends in on new developments and juicy slices of drama, I realized just how much I had to explain or elaborate on to the new friend, who hadn’t been there to get the play-by-plays as they happened.

I also realized that I wasn’t the relationship historian I thought I was– I found my other friends correcting me with a few details of my story, and when I thought about it, and I realized their memory was a bit more accurate.

Explaining to others what’s going on in your head and heart can be a tall ask, but it’s important. Talking it through helps ease some of the painful emotions that can come with navigating relationships, but talking about it can also help you figure out what you want, and what you don’t.

the match pro
Kimberly talked to us about the matchmaking process.

When it comes to matchmaking, your story is one of the most important parts of the process. You want to find a matchmaker who’s not just interested in that story, but wants to be a part of it. 

Kimberly Simonetti is a matchmaker, dating coach, and founder of The Match Pro. Kimberly joined and created the matchmaking service in 2015 to help people who are ready for long-lasting relationships connect and find love. 

Kimberly talked to us about how she found her passion in matchmaking, why her process focuses on your story, and gave some tips on how to deal when dating is feeling exhausting. 

“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 Focuses on What Really Matters

Before Kimberly was making matches, she was working as a professional photographer. She told us that when online dating started to pop up in the late ‘90s, she found people seeking her services for a slightly 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.”

the match pro
Kimberly has been helping singles find dating success since the ’90s.

That “new thing” was Match.com, and Kimberly’s clients were among Match’s earliest adopters. These clients were asking Kimberly for profile photos, and despite the newness of the online dating sphere, she knew that photos had to be one of the most important aspects 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 caught on immediately to how important photos are in the online dating world, an importance that hasn’t faded, and developed an approach that gave her clients organic but high-quality photos. When Kimberly decided to make the switch to matchmaking in 2015, she told us it felt natural.

Photographers often draw out the most striking elements of their subjects. In many ways, matchmakers do the same thing. 

Kimberly begins the matchmaking process with an in-depth interview, where she draws out the most important parts of your background and relationship goals, while not ignoring the important factors that may not be so easy to talk about.

Self Knowledge = 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.”

An expansive database is a good sign for a matchmaker, but it’s not the only factor that predicts success. Your matchmaker should want to get to know you on a personal level. Remember: this is the person who’s going to be setting you up on dates. You’re gonna want them to get you.

During the initial interview, Kimberly asks each of her clients if they’re ready to offer what they are 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 Kimberly hears clients’ lists of their must-haves, she encourages them to think about what they bring to the table, too. She told us this helps her clients level their expectations and gain clarity around the dating process. 

the ideal matchmaking client
During initial interviews, Kimberly helps clients decide if matchmaking is the right move for them.

It’s about making sure you come into the process with not just realistic expectations, but an open mind.

The first interview helps Kimberly get to know you, but it also helps her decide whether matchmaking is the right path. Matchmaking is for serious daters who are ready for mature, committed relationships. And mature, committed relationships take more than a desire to be in that kind of relationship.

Especially in the early stages. Kimberly said an open mind and an open heart make for the ideal matchmaking client. Once you’ve submitted your profile, chatted with Kimberly, and decided that The Match Pro is the right fit, you can choose from a variety of membership options.

Kimberly and her team help clients choose the membership that’s right for their goals. Once you have your membership, the real fun of the matchmaking process begins– the introductions. 

You get to focus on the fun elements of date night, like picking out the perfect outfit, while your matchmaking team takes care of the logistics.

After each date, you’ll check in with Kimberly. She wants to know everything about your date, from how you felt when you saw them to how the conversation went throughout the night. 

If it’s a match, she’ll help you reconnect if there’s mutual interest. If you weren’t feeling the date, Kimberly makes notes so she can make your next introduction even better.

“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.”

Let’s Be Realistic– Love is Out There

Matchmaking is for serious daters, but what does it mean to be a serious dater? And how do matchmakers make sure their clients and databases only have serious daters? Kimberly told us it all comes down to that initial 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 she can’t help people who fall on the low end of the scale through matchmaking. The way she sees it, matchmaking is at its most effective and enjoyable when clients are dedicated to finding love.

Matchmaking is a serious process, and Kimberly doesn’t want un-serious people disturbing the process.

hobbies and groups
You never know the people you may meet when you’re simply focused on living your life.

“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.”

If a client isn’t ready for matchmaking, Kimberly still has wisdom and direction to offer them. Sometimes, she offers resources like books and articles written by dating and relationship experts. She also points them in the direction of podcasts and coaching programs that can help with their specific situations.

“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.”

Kimberly’s approach to coaching and matchmaking is helping you help yourself. Matchmakers simplify the dating process, but they don’t make your perfect partner magically appear. You have to put in the work, 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.”