How to Win the
Dating Game

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Ep 1-How I Became a Matchmaker

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Ep 1-How I Became a Matchmaker

My parents led by example and taught me the power of two people being in love. Their other life lesson was the value of running your own business doing something you love rather than being employed. That your blood sweat and tears should serve your family first. For the next two decades, my destiny continued to be shaped by education, adventure, love, and heartbreak. My career was less a choice and more a result of inevitability. Find out how I became a matchmaker.......
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Podcast transcript

Hello, and welcome to the very first podcast episode of “How To Win The Dating Game”. I’m Trudy Gilbert, also known as Australia’s Millionaire Matchmaker, founder of Elite Introductions, and author of 49 secrets of an elite matchmaker. I’m super excited to be here, I’ve always dreamed of doing a podcast. And now, the time has finally come. And I’m really excited to tell you about why we’re here. And what we’re going to do together.

Okay, so just to give you some background, I’ve been an elite matchmaker for 17 years. And while I’ve loved every bit of that work, it’s really exclusive. And I only get to work with a select group of people every year, and I just wanted to do more. While my job during the day, I’m bringing the fish, I thought I could make more of an impact teaching more people to fish themselves. So I wrote a book quite a few years ago. And since then, I’ve had some amazing experiences and learned so much about what to do and what not to do in order to cultivate your dream relationship with your ideal partner that I wanted to write and teach more.

Now, we all know that there are amazing resources out in the world to help people through this process. And, you know, there’s a lot of different sources that you can tap into. But the more I researched, the more I discovered that there was a real need for a complete and comprehensive guide to support people throughout their romantic journey. And I’m talking about things like from the very beginning of preparing your mind, body and soul for your dream relationship to things like selecting your ideal partner, dating and interacting with them, building romance and chemistry, all the way through to developing, cultivating and nurturing your passionate, adventurous and fulfilling life relationship, and all the wonderful things that come with that. Things like partnership, the sharing and multiplication of success in all aspects of life, marriage, building a family, changing the world, whatever you seek with your ideal mate.

So as I have been developing our wonderful online program, which covers all of these aspects, I wanted to create an easy space for people to come together and reflect on the complex processes of dating and relationships, particularly in this crazy world that we live in with dating apps, disposable dating, the dilution of gender roles, you know, and also things like split or blended families, and the overwhelming complexities and demands of modern society. And to put the icing on the cake, try and manage all of this in a world where social interaction is restricted, regulated and even feared. So here we are, possibly in the safety of your home or car, maybe even on the treadmill, as my partner likes to do, or maybe pretending to be heavily involved. In a boring company, zoom meeting.

Wherever you are listening to me, I want this to be a space where you can take a moment to reflect on this important part of your life. acknowledge that it is complex in this modern world, but it is not impossible. It’s not magic. It’s something that you can greatly influence to your benefit. There’s a lot of science behind it, you can make a difference in your life. And I’ll be here to guide and support you through it. I’ve got your back. So this podcast series is going to be a lot of fun and hopefully offer you some incredible value. You’ll hear from me about my story, meet my amazing team, hear from some of my members, and also hear from some experts. And I’ve even got some celebrity guests in store. Just letting you know that there’ll be all kinds of structures throughout the series will do tips and guides, amazing stories, interviews, discussion panels, the whole works. We are going to explore the full gamut of the relationship adventure. Starting with you. How to prepare yourself better so you are open, receptive and able to command your dream partner? You need to be in a space where you will not repeat bad dating and relationship patterns and that you are fine tuned for the best outcome.

We’ll discuss dating in all different environments, and how to greatly enhance your chances of success. How to be more confident in your dating? Learn how to have more fun, play, flirt and build chemistry with anyone. Yes, I said build chemistry with anyone. It is possible. How to build romance and sexual connection? The pros and cons of modern dating? Why dating apps will never bring you the relationship fulfillment you are seeking? How to be successful in the dating journey so you can finally delete those dating apps? Oh, my God, I can hear a collective sigh of “Yes, get me off those apps”. How to meet people anywhere? Not just wait for your next friend’s wedding. How to offer more to a potential partnership, which increases your chances of having an amazing relationship? How to know if the person you’re attracted to and you’re enjoying being with is the right person for you to invest in? And how to do that in a way that will enhance that journey rather than sabotage it? Then, after that, we still have so much more to explore. Things like how dating and relationships are incredibly different and how important it is to separate and balance those two worlds. How to transition from dating to relationship and the safe, easy steps to do so that protect your new love. Finally, how to navigate the complexities of relationships? Things like blending and sharing lives, mixing friends and families. Making enough time for each other. Not making too much time though. Aligning values, sharing and supporting each other’s careers or other life pursuits. Building or blending families sharing assets and building them together. Marriage if that’s what you both want, how to manage things if it’s only what one of you wants? How to deal with personal struggles? How to support each other’s emotional journey without taking on too much? How to manage conflict, breakdowns, failures, betrayals, and growing apart? How to write the ship, building a family raising kids while keeping the flame alive, designing a whole life together. Okay, so grab a cup of tea or glass of your favorite wine, whatever you prefer. Sit back, and let’s get started. Okay, so before we jump straight into one of those meaty topics I mentioned to you earlier, I think it’s only apt that we go back to the very beginning. And I take the time in this episode to answer the most common question I get asked, which is, How on earth did you come to pursue this fascinating, but rather unorthodox career path? So here is my story of how I became a matchmaker.

So, you know, I mean, it’s a really unusual profession, right? It’s not like you wake up one day, and you go, “Hmm, I think I want to be a matchmaker”. It’s not like you go to school and you strive to achieve certain grades. And then you know, there is a career path that you take in order to reach this, you know, profession of matching people.

If anything, this profession found me, but it was also a part of who I am. It answers every kind of trait, skill, interest that I have. So it was basically an inevitability that this is what I was going to do with my life. And I have to kind of go back to my parents, and by upbringing to explain a little bit about, you know, how I grew up and where my focus was when it came to business. And you know, what I was going to do after school. So my dad was a successful business owner, he had his own agency in the rag trade, and he would drive around, visiting his clients. And one day I went out on the road with him. And I was young, I could have only been about, I don’t know, 10 or 11. And he said to me, Look, I’ll just do a little bit of work in the morning and then we’ll go and we’ll have lunch and we’ll go to a movie. So I happily tagged along with my dad, and we visited a few clients, and I noticed that he really enjoyed what he did. And when he went to visit clients, they would have a chat. And it was like he was visiting friends. They had this lovely little banter, they’d have a nice little chat for 10-15 minutes, then each show them a few shirts and they do some orders. And after you know a little while we leave and the same thing would happen again, we’d go to another store and you know, the chats, and then the business and then we’d leave. And I started thinking, well, this is a really great way to, you know, to work. We were also really fortunate that we had a really nice house, we were able to go on overseas holidays. And we had a nice middle class, you know, lifestyle. So I saw that my dad enjoyed what he did. He worked hard. And we had rewards for that we had a really nice, successful life. So that was my dad. My mom worked as well. She did a lot of bookkeeping for companies. And then she later got really involved in the Jewish community and was the head of Walpole hospital and was also heavily involved in the Australian Jewish Welfare Society. And her career really took off in the Jewish community, and she was actually awarded an AI. So I’m amazingly proud of what my mom was able to achieve. Now, I can remember my mom sitting on the sofa at night, and she wouldn’t be able to watch TV just, you know, switching off, she’d always have a project to do, she’d sit there with a notepad from work, and she’d be working out, you know, a roster schedule, or she would be working out a new marketing campaign, whatever it was, she was sitting there, and she would always kind of, you know, work on something.

So, yeah, I had a really strong influence from my mom and my dad, who kind of made me feel that if you work hard you can achieve great things. I then went to uni, and I studied psychology, social science and sociology. They were the three subjects that I was drawn to, I wasn’t quite sure what I was going to do. You know, I just thought, well, I’ll pick subjects that I like that, you know, I think I’m good at because they interest me. And they seem really relevant to most aspects of life. You know, I hadn’t really figured out what direction I wanted, but I thought, look best to do things that I enjoy. After uni, I went and lived in Italy, for a couple of years, it was one of the best decisions I ever made, I wanted to be an opera singer, when I was younger, and in my early 20s, that’s what I that’s what I really put a lot of my energies into. And, you know, I have a very strong interest in music, which was fostered by my dad as well. And I just love opera. And I’m very passionate, I am very interested in, you know, the arts. And I thought, well, this is going to be you know, this is the direction that I should be heading towards. So I then went and enrolled in a language course in Florence for a couple of months and learned Italian and then found a teacher and studied singing in Florence for a year. And it was amazing. And after a while, though, I started after about three or four years of singing, I thought, look, do I really want to invest my time and energy into an art form that I can’t be sure I’ll be successful in? You know, yes, I enjoy it. I love it. But, you know, do I really want to spend the rest of my life doing this? And I guess my business brain kind of took over my artistic side. And went, look, why don’t you just do this as a hobby, as a fun thing on the side and really focus your energies into building something that, you know, could actually lead to a successful life.

So I started my own business in Italy . That was my first foray into the business world, I was a consultant to companies that wanted to learn where they wanted their staff to learn English. So a bit more than just an English teacher because what I would do is create courses specifically for their staff, get in my car and drive around all parts of I was living in Bellona at that time, and teach them English. Teach the staff at companies English. And that was amazing. I loved doing that for three years. I did that. If anyone’s listening and they’ve been to Italy, they’ll know what I’m talking about. That the people are amazing. You know, they’re so warm, they’re inviting, they are you know, they have the right balance of their attitude to life is just not living to work but living to love. You know, living to enjoy life. The food, you know everything about the Italian way of life just resonated with me. And I felt very much at home. I don’t have any Italian ancestry, or background, but I picked up the language really quickly. And it just, I felt like I was in the right place. So, after about four years of being in Italy, my dad got sick and I needed to come home. So I did. And he was fine. But we were a little scared. You know, he had a minor stroke. And he recovered really well. So I started thinking, Okay, well, What now? What’s my next step?

And I, you know, it was, there were certain things that were really clear to me, one was that I knew I loved working with people that, you know, I love the passion of the Italian culture, the romance, I really enjoyed helping people I really enjoyed, you know, contributing to their lives, and having a strong connection with them, you know, my students would become friends. And every course I taught in Italy, I would I, you know, take two or three of them and keep them with me, you know, and I’d collect a little group of friends after, after all of these courses that I taught that at my farewell, I had, like, you know, nearly 80 people at my farewell when I came back, you know, to Sydney, which was really extraordinary after, you know, being in a foreign place for three years, I had a really strong friendship base. So I was thinking, Okay, well, how can I, what can I do that it allows me to work with people taps into the skills that I’d learned at university with those courses of, you know, psychology, sociology, and social science, that allowed me to make a change in people’s lives that allowed me to have a close connection with them. I had all these pieces, but they weren’t coming together yet. But I knew that it would happen, I knew that in time, everything would fall into place. So it took me probably about another couple of months. And I’m still racking my brain for what my next move is. And I sat down to have a coffee in a cafe and I reached over and grabbed this glossy magazine. It was something like a clear or Cosmo or glamour or whatever it was. And to this day, I really wish I could remember the name of the magazine and I have searched for the article that I read. But I’ve not been able to find it. And it’s been really frustrating, because this article absolutely changed my life. You know, I’m not sure if you have moments that you look back on, and you go, that was a turning point for me. And I’ve got a few which are, which are really amazing. But this was one of them. This article, my brain just started lighting up with possibilities as I read it.

So essentially, it was a story of a woman who is a high end matchmaker in New York. And she promised, you know, I don’t know how but she promised to find you a partner within three dates. Now, her service was very much over the top, it was for the New York high society, it was something like 50,000 US for the service. And you know, the article went on to say that she would send you on three dates. And then if you didn’t like any of the three dates that she had suggested, she should drag you into the office, sit you down and say, well, you haven’t been honest with me about your criteria, because I’ve matched you perfectly. Those three people were your perfect match, and why didn’t you connect with them? And I was like, wow, this is really, this is really hard core, but a part of me went “Hang on a second. There’s some potential here. What if we had a dating agency here in Australia, in Sydney, that helped people meet like minded people. Now what I mean by that is, I grew up in a middle class household. I went to private school. I liked to travel. I liked to go to the opera. I liked, you know, learning and growing all of these things. What if I found a way to connect those people together through this agency? You know, sure. They were dating agencies that were around and had been around for a long time, but they weren’t targeted to this demographic to people with this shared value or shared, you know, lifestyle”. So I started thinking, this lady’s agency that’s really high end. That’s too high end for the Australian market. What if we made it for business owners and professionals? What if it was just for the executive and the more research I did, the more I found that that style of dating was really popular. And in places like the UK in the US, this executive matching matchmaking was the new next thing. So I thought, “Okay, great, I’m onto something here, this has got real legs, I can give great value, I’ve got all the background, I’ve got all those skills that I studied at university, I love dealing with people. And this really could be, you know, my next move”.

My philosophy was that I genuinely believed people with similar values, lifestyle, interests, educational background, life experiences, and social compatibility would connect better. You know, when you are meeting someone, there are so many variables that come into play, you know, do you have the same values around? family? Do you have the same work ethic? How are you both educated? Do you like to travel? You know, do you both enjoy, you know, exercise, things like that. And I felt that the more that you are able to control those variables, by having them being similar, the greater the chance for connection and compatibility. You know, it’s like, being in a party where everyone is in your crowd, or, you know, like, we talk about meeting people that are from our tribe. I wanted people to have the confidence that they knew that coming to my agency would mean that they were meeting their fellow tribe members. And, and that’s what inspired me to feel like I was making a difference. I was giving people a hub, you know, like I say to people now that speak to me, that inquire about joining the agency, I say, look, would you rather swim in the ocean and hope that you bump into someone who is, you know, like minded? Or would you rather be in a pond with everybody who is the same as you, and that you have a greater chance of connecting because you share alignment in all of those aspects, values and lifestyle and interests and so forth.

So the agency was born in 2005, which is now quite a while ago. I had a lot of PR when I first started, and, you know, there was a lot of buzz around the agency when it began, which was great. And I have a really special story that I want to share with you about something that happened within the first six months of starting my business. Now, as I said, I got a lot of coverage in the newspapers and you know, magazines, and you know, there was even a bit on TV, basically, what happened was that I got a call out of the blue from a friend that I went to school with. And, you know, it had been a while since obviously, you know, school had ended, and I hadn’t really maintained a connection with this particular friend. So I was kind of surprised that she called me. It seemed like just, you know, completely out of the blue. And she said to me, look, I’d really love to come and see you, I’ve got something that I want to share with you. And I was like, Okay, all right. Well, this, this is intriguing. And she came to my house, we had a lovely, you know, catch up. And she told me that she’d seen one of the articles in the paper about my new business. And I said, “Yeah, you know, it’s, you know, I’m really excited. I think I can really offer some great value to people”. She said, “Well, I want you to know something”. She said, “Do you remember back in year 11, you introduced me to this guy that you thought that I’d like”. I went to a co-ed school but you know, he went to another school and I knew him fairly well. And I thought, Yeah, I thought she’d like him. I said, “Yeah, yeah, I remember that. She said, well, we’re married, and we have been married for the last 12 years and we’ve got three kids and we are blissfully happy”. I was so happy to hear that. I was beaming. I was just absolutely shocked. I had no idea that I had created my first success story at 17. Before I even knew that I wanted to do this. My friend came to tell me this so that you know, she was like you’re on the right track. Do you have to continue? It was affirmation from the universe from my friend that I was made to do this job. And I was so grateful she It was such a wonderful opportunity that she came to see me, she brought me a beautiful platter as a thank you, which I still have and use to this day that I was just really, really chuffed that, you know, I’ve been able to make a difference in her life.

So that was a lovely, lovely thing that happened. And you know, the agency grew. And you know, we started matching people. I remember I had my first marriage, which was after a year that the agency was open, she came in one day, and he came in the next day, and I just knew that they’d be perfect for one another. And the funny thing about this story is that she rang me five months later to tell me that they were engaged. And she said, “You wouldn’t believe it. But we both have mutual friends that had been wanting to introduce us, but never got around to it”. And that they had to meet through me. So I thought that was kind of cool. And that was Jessica and Hugh, I’ll never forget them. Now my first first marriage, then we had our first babies, then we had, you know, you know, other marriages and, and people moving in together all sorts of successes, which was, you know, really, really wonderful. And then something weird started happening, you know, I would look at the matches, and I would go, look, you guys are so compatible. Put two people together, they’ve got so much in common, similar life stage values, you know, experiences, interests, all of these things. And sometimes the matches would work. And sometimes they wouldn’t. And I couldn’t quite figure out where it was going wrong. You know, wasn’t that like, what happened with the lady in New York where she would, you know, wonder if they were being honest with their criteria? Was it that people weren’t being straight with me about what they wanted? These people seemed so well suited, but it wasn’t working. So I had to figure out why they were not working. And I realized that, maybe they were messing it up, maybe they didn’t have the right skill set, that, you know, they were doing things on their date, that was sabotaging their own experiences. And part of my process is getting feedback. So when I would get the date feedback from both parties, I could understand what was happening and why it was falling over. There were things that they were doing, that were causing things to not run as smoothly as they could have. And I realized that I could greatly influence the success of the dating process by tweaking things, and some people needed minor tweaks, and then they would get the most amazing results. And, you know, it would be the difference between being single and being in a relationship. And other people needed a lot more work. And they needed to really learn about some of the basics, the do’s and don’ts, the you know, wait mindsets that you need to get into. Things to prepare for the dates, and how to manage that awkward stage of the unknowing, you know, the anxiety of not knowing where it’s going and being able to sit in that space and be comfortable with it. So often people will just get too anxious, and they’ll want to know, or if they like me?, you know, why hasn’t they replied to my text? Or, you know, where is it going? What’s happening?

I found that, as I said, some people needed a little bit of assistance, but other people needed a lot more. And you know, in today’s society, it’s very complex. There are dating apps, and there’s a disposable culture towards that. There’s a hookup mentality, modern social issues around gender and equality, the blending of gender roles, and then throw in social distancing and COVID. I mean, it’s a minefield. And I realized that people just needed a bit of knowledge and practice, which could then change the path of their happiness in their love journey. So I realized that I love doing what I do. I enjoy helping people and I’ll continue doing it. But I couldn’t, can’t help enough people that way. I only get to work with a limited number of people a year. And I wanted to help more. So I thought, well, what’s the best way to do that? And that’s to do a podcast to offer my advice, my guidance, my support, my tips, my trickS. Help, more help create more happy ever after stories for people. That’s why we’re here to do exactly that. Well, I hope I got to answer my most frequently asked question of you know, how I came to be a matchmaker. And you know a bit about why we’re here and how you could benefit from this podcast. You could be single and looking for a partner. Or in the early stages of dating someone, if you’re married and struggling with things or wondering if the person you’re dating is the right one. Wherever you are, there’ll be a lot of valuable information for you here. And I tell you, you’re going to find it fascinating because we are going to talk about things that people don’t normally discuss. I recommend you log on to and that’s Trudy with a Y and take our quiz to see if you’re ready for your dream relationship. It only takes a few minutes, but it will make sure that you’re in the right headspace and shine a little spotlight on things that you may need to tweak so that you can have the relationship of your dreams. I look forward to seeing you in the next episode. We’re going to get right into things straight away. So welcome to “How To Win The Dating Game” and see you next time.

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