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Interview with a Matchmaker: Dating Coach Spills the Beans to Finding Love in Boston

When people meet a professional matchmaker, lots of questions inevitably arise. What’s it like? How do you find people? Are you successful?

So in order to give you a better perspective, we at LunchDates have interviewed Jaime, one of our top Executive Matchmakers. Jaime brings over eight years of professional matchmaking experience to the table. And getting Boston singles into a relationship is something she takes to heart.

So I sat down with Cupid’s arrow and asked her to give me the down and out truth about what it takes to be a successful matchmaker.

Question: What made you decide to be a matchmaker?

Answer: Before matchmaking, I was actually a felony probation officer in a DA’s office. I was constantly matching up my friends and co-workers. And I was successful! I decided to go from probation officer to professional matchmaker.

Question: Can you tell us a success story?

Answer: I have had so many success stories, but one of my favorites was an executive client in her fifties, who was widowed. I worked very closely with her. She was extremely discouraged after losing her husband and thought she would never find love again. I introduced her to Bob* and they fell in love. He, like many of my male clients, was a busy professional, a CEO, who happened to be recently widowed as well. Bob wasn’t sure if he was ready to get back out there. After some coaching, he was introduced to my client, Marie*. They fell in love, dated for a year. Now they’ve been married for almost a year and are enjoying their time traveling the world together.

Question: What do you think about online dating?

Answer: Usually by the time a lot of my clients come to me they have tried of online dating, but they prefer the privacy and confidentiality our service provides.  They also appreciate the fact that we do all of the work to arrange their dates.

Question: What’s the biggest myth people believe about dating?

Answer: Many singles think the more they date, the better chance they have of finding Mr./Mrs. Right. That couldn’t be further from the truth! My clients come to me because they do not want to waste time dating for the sake of dating. It’s much better to go out with fewer people that are truly good matches rather than dozens of dates with the wrong kinds of people.

Question: What’s the one area you work on most with your clients?

Answer: Presenting their best self while on a date. It’s easy to get caught up in the drama of a hard work day, especially when you’re in a high profile job like a lot of my clients are. But, it’s critical to be able to turn off all of the noise and relax while enjoying yourself on your date. I want to create a dating atmosphere where my clients can be themselves and have fun!

Question: What’s your biggest strength as a matchmaker?

Answer: Listening to the needs of my clients. We have feedback calls after their dates so I can fine tune what it is they are really looking for. When we move forward with their input and my coaching, they get into a relationship sooner. And ultimately, that’s why they’re working with me. To see results.

Question: Do you have an ideal client?

Answer: Anyone! Everyone! My Ideal client is a busy professional who is ready to make dating a priority. Typically my clients live and work around the Boston area (but not always) and are tired of going on lots of first dates.

Question: How should people contact you?

Answer: We’re extremely busy. But, that being said, we are always looking for great, quality singles. The best way to reach me is to call the main line at 617-254-3000.

After speaking with Jaime, I realized I needed to take some of her advice. How have I sabotaged myself from finding a great relationship? Personally, by making excuses for not putting myself out there and giving up after lots of first bad dates. But my dating shortcomings won’t be the same as everyone else’s.

Know that a little coaching can go a long way when it comes to dating. If you want to check in our your dating status, I suggest giving Jaime or anyone else at LunchDates a call.

At the end of the interview, I walked away with a few very clear understandings when it came to the world of dating.

Takeaway #1: Jaime’s clients are very lucky to have her. Plus they get the benefit of finding that forever person they’re looking for!

Takeaway #2: You have to be proactive and put yourself out there.

Takeaway #3: It’s never too late. Any age, any time in your life, you can find love.

Takeaway #4: There are professionals that truly want to help you and get you into a relationship.

So Why Aren’t You Working with a Matchmaker?

LunchDates has been matching Boston singles for over twenty years. Our team of professional matchmakers and dating coaches understand what the challenges are in today’s dating market. If you’re not having success on your own, give us a call! We want to help you find love.

Aimee Burke has over a decade of experience as a relationship coaching professional. She is an avid writer and researcher for the Boston dating scene. She’s also the main contributor to LunchDates’ dating advice blog.

*Names have been changed to protect the privacy of our clients. But their love story is real!


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