7 Secrets Of An Elite Matchmaker

Trudy Gilbert is a modern-day cupid, but instead of donning wings and shooting a bow and arrow, she wears a killer pair of stilettos and uses psychology and instinct to match-up some of Australia’s most powerful singles.


With almost a decade in the industry and with a degree in Social Science and Policy and a background in Psychology, Trudy is known as the Millionaire Matchmaker. Trudy has learned a thing or two throughout her career, so the first moment I got, I asked her to divulge her top 7 secrets into men, dating and relationships.

Secret 1:  A strong woman

Many women mistakenly believe men are looking for a weaker woman who will allow them to feel smarter and more powerful. Seriously, a great guy is not intimidated by a woman’s success or independence (only a man who is insecure and who has not achieved his own success and is still struggling to find his place in the world will feel threatened by a driven and accomplished woman) . So what type of man is? What type of man needs to prop himself up by putting others down? Certainly not a man I see as being a potential suitor. Nothing could be further from the truth for my clients. I am here to proudly state that my male clients, my successful and confident male clients, not only enjoy the company of an intelligent and self-assured woman, they actually request it as one of their top criteria. Men love knowing that a woman has her own life. Really they do. They love knowing that she has her own friends, interests, responsibilities and commitments. Men want to know that you have time for a relationship and that you have time for them, but not too much time. Men enjoy knowing that you have your independence.Irrational as it may be, but men are sometimes afraid that you’re going to turn into some obsessed bunny boiler whose main focus in life is planning your wedding after date number three. They want to know that you’re already on your path to being a complete and secure woman.

Secret 2:  Sensuality & femininity

I recall meeting one prospective female client who came to the agency many years ago. Even after all these years, I still remember her like it was yesterday. She was early 30’s, slim, attractive, a finance professional and very successful. We sat down and I started the interview process. As she told me about herself and her criteria, I noticed that she spoke with strong conviction, very much like a man. She didn’t so much as request what she was looking for, but demanded it. She was direct, extreme and intense. She was what we might describe in layman’s terms as a “ball breaker.” This girl was tough. As the interview continued, I noticed that I started feeling anxious and uncomfortable. Her intense masculine energy was stressful to deal with — and if that was something I was picking up on, what would it be like for my male clients? She’d lost all softness, all her feminine energy and charm. Of course, she’d just come from work, where she was used to operating in a male-dominated environment. Nonetheless, somewhere along the way she had lost touch with her feminine self. From boardroom to bedroom — was her lack of dating success due to the fact that she couldn’t leave her work persona at the office? Had the men she’d met felt like they were in a business meeting rather than on a date?

Mature masculine men want feminine women. It’s as basic as that. They are drawn to your confidence and sex appeal, as you walk into the room. So —take the extra ten minutes to pull the LBD (little black dress) from the back of your cupboard. You shouldn’t feel pressured to strut around the bedroom in lingerie and high heels every night, but you should feel comfortable with your own sensuality, and expressing that to your man. Now let me ask you, as a woman, don’t you love the fact that you have the power to beguile? We know that using our sexuality is a powerful tool for attracting men. Tasha Tudor, an American illustrator of children’s books, explains it perfectly: “Why do women want to dress like men when they’re fortunate enough to be women? Why lose femininity, which is one of our greatest charms? We get more accomplished by being charming than we would be flaunting around in pants.”

Secret 3:  An equal

“I want someone who is intelligent, emotionally stable and down to earth”, is often something I hear from my male members. A woman’s intelligence is more attractive to men than ever before. Men are looking for women who are both educated and intellectual — or in other words, accomplished and interesting. Smart, savvy women are capable of longevity in terms of intrigue. When men are considering a serious partner, they look for a woman who can stand as his equal.The next preferred quality is emotional stability and maturity. Women are emotional beings, let’s face it —it’s how we’re built. We watch The Notebook and tears effortlessly stream down our cheeks, and at a certain time of the month we make The Hulk seem like a wallflower and we have an absolutely intense and irrational fear of anything that crawls. However, it’s one thing to be an emotional human being, but it’s another thing entirely to be overemotional. Too much emotion, too early, can set off warning bells to a guy. It can seem needy and immature. Showcase that you’ve outgrown overemotional tendencies from the get-go.

Secret 4:  Down to earth

A friend of mine was dating a fabulously attractive girl who was the complete antithesis of this phrase. She was the most spoiled and pretentious person I’d ever met. On her birthday, he’d shower her with gifts and take her to the most expensive restaurants, but it was never enough. She always wanted, no hold on, demanded more. He bought her a beautiful pair of diamond earrings, which she gave back to him to return (as they weren’t big enough). After a time, cracks in the relationship started to show and the couple split after a few months. Being materialistic and high maintenance are huge turn offs for guys. Yes, he wants to treat you like a princess, but it doesn’t give you the right to act like one all the time. Let him organise surprises, buy you jewellery and welcome you with flowers when he wants to — not because you demanded it. The more pressure you put on him for such things, the less he’ll want to do them. Becoming a more down-to-earth person will provide you with numerous benefits. Not only will it come across as appealing to men, but it will also help you deal with life’s ups and downs with a little more grace. It’s not all going to be wine and roses. Having the ability to keep things in perspective is the trait of maturity.

Secret 5:  The chase

We’ve all heard that men love to hunt. They relish the thrill of the chase. It’s a biological, primal desire. Neither man nor woman can deny it.  Men seem to possess a DNA-based disposition to claim a woman as their own.
The key is self-worth. If you respect yourself — whilst politely and kindly encouraging only his best behaviour — a great man will scramble to please you and work towards taking you off the market. This is why some men tend to chase after women who push back; refusing to be immediately seduced by their charms (this is especially true if the man is used to women falling at his feet). Falling in love involves being resilient and positive, it will encourage a man to be his best. Determine your own self-worth; don’t accept “friends with benefits” as a substitute for a real relationship.

So girls, stand high in your Jimmy Choos.  Setting standards will allow him both the pleasure and pain of the chase. I know this is easier said than done, and depending on your generation, women often approach guys — and if so, more power to you. There’s zero harm in letting a guy know you’re interested. However, I firmly believe that if a man is truly interested, he will pursue you. He’ll call and ask you out (or text to ask you out). The phrase: “He’s just not that into you” enlightened women worldwide in terms of deciphering male dating behaviour. If he isn’t calling, he simply isn’t interested and this is your cue to move on. If you’ve been on a date with a guy and he hasn’t called you within seven days after the date, it’s pretty clear that he’s just not that into you. If he does call after seven days, he’s most likely interested in a booty call — thus, you’ve moved past the potential partner phase to the friends with benefits stage.


Trudy has just released her new book, 49 Secrets of an Elite Matchmaker available from www.eliteintroductions.com.au (RRP $14.99 )



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