How to Win the
Dating Game

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Ep 2-Work Zone Date Zone

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Ep 2-Work Zone Date Zone

In order to have romance in your life you not only have to make the time for it but the space for it. Much of that space is in your own head. Trudy shares the tips to stop you from sabotaging your dates.
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Podcast Transcript

Hello and welcome to Episode 2 of “How To Win The Dating Game”. I’m Trudy Gilbert, also known as Australia’s Millionaire Matchmaker, founder of Elite Introductions International and author of “49 Secrets Of An Elite Matchmaker”. We’re here today to discuss the treacherously wonderful world of dating and relationships, where we’ll explore everything from preparing your mindset to identifying and wooing an ideal partner, right through to how to cultivate and nurture an incredible relationship.

In the spirit of preparing you for dating, this episode is about getting into a mindset of success on your dating journey. There will be numerous episodes about this very topic. But today, we’re going to talk about shifting into a dating mindset before your date. It’s called, “How to get out of the work zone and into the dating zone”.
Trudy: It reminds me of the song you know, highway to the danger zone. Sorry, okay, I sometimes do that. It’s my, you know, little quirky thing. Okay, so let’s jump right in. I’m here today with Andy. Say, “Hi, Andy”.
Andy: “Hi, everyone”.
Trudy: Who is part of the elite team and is also my wonderful partner.
Andy: Yeeey!
Trudy: So team, team elite and team Trudy,
Andy: That’s right.
Trudy: …represented here. You’ll meet the other members of the team, Lisa, and Jody in upcoming episodes, and they are also awesome. Okay, so parts of the advice that you’ll hear in this series may sound obvious to many of you. But you would be amazed at how many people are often very intelligent and advanced people who make these mistakes over and over. So I want to make sure that you don’t. Okay, let’s get started! Tip number one. Make the time for your date. Don’t squeeze in a quick coffee or lunch date? How many times have I told people not to do this?
Andy: So what is it? I mean, people can be quite busy. What is it about? One of them about the lunch date that really, you know, rubs you the wrong way?
Trudy: Well, okay, the coffee. Let’s start with the coffee thing. A coffee date is what you do with work colleagues. It’s what you do with friends, your girlfriends, you know, after your spin class, and you’re still in your active gear, let’s go and have a coffee. It’s not romantic, you know, and the lunch date, okay? It’s just it’s, again, what you do with friends. It’s, it’s a limited time frame that you’re putting around the date, it’s telling the other person look, this is I’m only giving you 40 minutes of my time, I’m only giving you an hour,
Andy: I can squeeze you in,
Trudy: I can squeeze you in, in this tiny little window of my life. And it also says to the person or makes them question, what does this person have actual room for a relationship? Are they going to be able to make the time for me? But apart from that, it says low commitment, low investment to the process. So you know, I just don’t like it. I don’t think coffee is sexy. I think you’re immediately putting your date into a friendzone. You know, don’t you want to date to be a bit romantic and go and have a drink and get dressed up to look sexy.
Andy: It probably comes from the numbers game to dating apps and stuff. So you know, they’re going through so many people that they think well, it’s just too much.
Trudy: Yeah,
Andy: Too much commitment to make to any one person because I’ve got, you know, nine other dates this week. So they’re like, I’ll just squeeze this person in for 20 minute coffee and see if it’s worth going to the next day. So it’s all about
Trudy: Yap!
Andy: It’s badly influenced, I think by this disposable dating culture that you keep talking about.
Trudy: Yeah, look, I agree. You know, people are over it and they don’t want to invest time with people that they’re not certain of. So they want to go with the briefest possible catch up, which is a coffee. But I would challenge that and say just change it to a drink, a drink can also be an hour, but it gives you the opportunity that if you are connecting, you can extend that time and you can order another drink you can order some food. You can keep going if there’s chemistry. If you’re enjoying each other’s company. What do you do at the end of a 40 minute coffee? Order another one? I mean, it’s not a very–
Andy: Go back to work is what’s actually happened.
Trudy: Yeah, I’ll go back to work or whatever. It doesn’t set it up for success for allowing things to continue. If you’re going well. You need alcohol on the first day, you’re going to be nervous. Have a drink, not an espresso shot, not make you more nervous and jittery.
Andy: We’re not we’re not promoting alcoholism, but if you’re safe. You know, if you’re a healthy user of alcohol, then it can definitely help just to lower the barriers and give you a bit of dutch courage.
Trudy: That’s right. All right, tip number two. Ideally, book your date for the evening. Don’t double walk yourself. Don’t–
Andy: Oh! You mean whole evening,
Trudy: Yeah! Like don’t say, I’ll meet you from seven. And then at nine, you’ve got to go and do something else. You know.
Andy: I’ve seen a lot of advice like that, you know, I’ll just make sure you’ve got something to do afterwards, it lowers the pressure of the situation, but you just kind of telling them that you again, that you just kind of squeezing it in.
Trudy: Yeah! it’s like, you know, I’m, again, I’m too busy. It’s game playing, it’s you’re not being genuine. You know, you want to show that your date that you respect their time, that you know, leave the opportunity for things to blossom. If it is, you know, if that vibe is there, then you’re giving it time to develop so that you can be in the moment and enjoy it. Knowing that you’ve got another, you know, appointment at a certain time will create a bit of pressure in the situation because you’re at the back your mind going, “Oh, how much longer do I have if I got to leave soon, you know, a bit of check the time” and that makes the other person feel a bit anxious. You know, just just don’t do it. There’s no need.
Andy: When I saw this bullet point in your notes, I thought you were talking about for the evening versus the daytime. Are you talking about that as well? Like when you say this?
Trudy: Um, look, that’s a good point. Because you could see it that way. Look, I don’t mind a lunch date, as long as it’s by the water. You know,
Andy: On a Saturday,
Trudy: On a Saturday or Sunday. You know, you’ve got you can settle in for the afternoon.
Andy: Our first date was at the beach?
Trudy: You mean our second first date.
Andy: Our first date
Trudy: After many years,
Andy: After that when we reunited that first date was down at Kouji. And it was about five o’clock on a Friday.
Trudy: Yeah, it was great.
Andy: … and it was a couple of drinks. And there’s a DJ there. I mean,
Trudy: Yeah,
Andy: It’s almost like a night vibe.
Trudy: That’s right. Yeah, that’s right. But yeah, like there’s nothing wrong with a day date. But just leave that let there be a couple of hours or more for it to you know, continue.
Andy: Some people like activity day dates as well. So,
Trudy: Yeah, well, you know,
Andy: You might need it to be
Trudy: During lockdown. You don’t have much choice do you?
Andy: Go on to be cold right now. But you go kayaking, or something like that. I think that’s a nice date. Go jumping in a kayak, do something adventurous, but then plan something afterwards. You know, like, do that if everything’s going well then go to like, the bar afterwards and have a drink or
Trudy: Yeah, I love that. I love that and be as creative, you know, as you want. I know. I don’t know if you remember. But I had one of my funny stories about a couple who had their first date. They went out. They met the head of 27 hour first date
Andy: That’s right. You told me about this.
Trudy: They went and had a meal. I think …. So like at one of those lovely restaurants on the wharf found out they had so much in common, jumped in the car, drove down to Thredbo and went skiing for the day and then drove back
Andy: 27 hours.
Trudy: Yeah.
Andy: Well, for the people that aren’t from Sydney. Thredbo is a five and a half hour drive. So there’s 10 hours of that was in the car.
Trudy: Yeah,
Andy: That would have gotten down to the nitty gritty there for sure. Yeah, I’m on my way talking and have definitely found out a lot about each other and that time
Trudy: Good on them for being you know, impulsive like that and having fun.
Andy: Yeah, that’s, that’s true. It’s about being Yeah, being impulsive and, and just reacting to the moment. Going with the moment and having the freedom to Yeah, it’s very impressive.
Trudy: Yeah,
Andy: If you just go, You wanna come, Yeah! Let’s go!
Trudy: Absolutely. It’s hot and sexy. And imagine if that if either of them said “Oh, no, I’m meeting a friend afterwards” that opportunity would have been missed.
Andy: I got work on you know, I’ve got to work. I’ve got a presentation on Tuesday and I really need to go home and practice, “Oh! God”
Trudy: Neeext! Okay, now what have we got? We’ve got the next tip: the best case scenario is to create a physical and time space between work and date. You want to be able to shake off that work energy. Now this is really important.
Andy: You may actually go do something physical like go to the gym.
Trudy: Yes
Andy: Go for a run or something like that.
Trudy. Yes, that’s exactly what I mean. For men that a 100% go or women you know, anyone go and do an exercise class could be yoga could be a run, whatever it is that shifts you from that work space into a different space to help you be a bit more relaxed. You know, there is some real, some very hard, you know, scientific evidence that advises you to exercise before a date, because it makes you feel more comfortable and less anxious on a date. You know, do you feel that good advice for men,
Andy: Yeah! I think it’s good advice. But also, on top of that, and goes with some of the sites that I’ve, I’ve looked at that, you know, you, you go train, you feel more masculine, you know, you do because you feel strong. You know, if you do weights and stuff like that you get, you know, testosterone boost, you feel stronger, and it’s part of, it’s part of that roleplay, that men will and roleplay that you want to explore in that date scenario. Trudy: Mm hmm. Yeah,
Andy: For a lot of reasons, I think it’s a good,
Trudy: Yeah, I that I get that. The other thing I want to say about this is that women, you need to get out of your masculine energy that you’ve probably been in during the day at work, you know, you’ve been making decisions, you’ve been, you know, you know, in meetings back to back, you’ve been leading,
Andy: Leading people
Trudy: …leading people, managing staff, you know, doing all that kind of, you know, all those chores, that really heighten your masculine energy. And what you want to do is, is shake it off, and tap into your feminine energy, because you don’t want to turn up on your day and start, you know, being the man, you know, asking all the questions, leading the date,
Andy: Making all the decisions
Trudy: Making all the decisions you want to not do, you really don’t want to do that. So
Andy: It’s about role plays isn’t it? It’s a game and we really need to, to play the masculine feminine roles out and tapping into that, that, you know, evolutionary part of, of the process that makes it more fun and playful. And I think that’s a huge part of where chemistry comes from.
I totally agree. Look, you know, babe, you know, that I’m a big believer in traditional gender roles, I really think that they work because, you know, it’s evolution that’s, that’s printed into us, you know,
Andy: Particularly in the early stages of dating, you know, you want to be able to establish chemistry and chemistry comes from those, those roles.
Trudy: It does. Women find it sexy and attractive when a man is masculine, and he takes charge, and he makes the decisions or he takes the lead or he plans the date, all of that is really purposeful in dating, because it makes her feel that he is making an effort. And that’s respectful, and that makes her go “ Oh, he’s that he’s thoughtful. He’s lovely. He’s, you know, charming, he’s, you know”, it increases his stock in her eyes. So it’s 100% you know, important
Andy: Look at the dream. The dream guys in women’s eyes is like George Clooney, you know,
Trudy: and Daniel Craig,
Andy: That Bond thing or Christian from 50 shades, you know, they’re, they’re powerful. Trudy: Yeah,
Andy: You know, they make decisions, they’re their leaders. They’ve got it all going on, they’re in control, you know, all those things, you know, they’re very masculine traits. So it’s hard to deny. No matter how much of a modern woman or a modern man you are, it’s hard to deny that you know, we respond to these role plays.
Trudy: That’s right. That’s right. So women you want to get out of your as I said masculine energy and tap into your feminine energy and there are a number of ways that you can do that. So let’s quickly touch on some of those you know, it could be having a bath, putting on your favorite music and you know, having a glass of wine while you get ready. Again, I’m promoting alcohol now.
Andy: But I definitely I mean, obviously for if you’re a guy you’re probably not going to go for you know, the bath and the scented candles but I definitely love to put on some music
Andy: You know, when I’m getting ready and pumping through the house and you know, whether I was doing it before I was dating. But even now when we go when we go out on a date, I love you know, to have the music going for us to sort of get into the vibe before we go out we have a lot more fun once we’re in the headspace
Trudy: Yeah, 100% it’s um, you know, if especially if we’ve been working or you know, or you know, recording a podcast and then it’s time to go out we’ve got to we’ve got to shift our energy and the best way to do that is just to do something that breaks it and you know, go “Okay, well now we’re doing this activity so I’ve got to get into the I’ve got to get my head in the game”.
Andy: Well, even though we work in different parts of the business, you know, you’re still the boss. You know, it’s your baby. You’re still the boss and that headspace,
Trudy: Don’t you love that woman?
Andy: but
Trudy: Here I am talking about traditional gender roles.
Andy: Yeah, but you know, like, there’s women out there that are spending the day, you know, breaking through the glass ceiling. And, you know, you’ve got to, you’ve got to, you’ve got to shake it off because we can’t go out in that same headspace that won’t work.
Trudy: Oh, yeah.
Andy:And you, you shift
Trudy: I do,
Andy: I got to give you a compliment you should quite, quite beautifully into “Okay, now it’s time for me to be, you know, a lady and dress up. And you know, and you loved me to do things like plan in the evening and stuff”. You know, you go into that role? You know,
Trudy: I do.
Andy: It’s 100 miles from where you were a few hours before we were running the show.
Trudy: Yeah, Thank you. Thank you, baby. Yeah, I do that. And I find that things like a bath or putting on my favorite, my favorite dress immediately transforms me into my feminine side, you know, my favorite heels, you know, my hair, how I you know, if it’s up or down, whatever the outfit wants, you know, determines, I find that whole, you know, presentation process really shifts me. So that’s actually one thing I want to mention. I had someone ask me, you know, recently what should I wear on a first date? You know, it’s a typical question.
Andy: Is it a woman or a man?
Trudy: And it was a woman. And she said, Look, I’ve sometimes met people for coffee after the gym in my activewear. So what do you think of that? And I’m like, Well, okay, first of all, the coffee thing? No, activewear Absolutely not. I’m like, I tell women to wear a dress, to wear something that, you know, highlights their figure that makes them feel sexy. You know, let’s let the women who, you know, what you think a woman should wear all day?
Andy: Sure. I mean, I, you know, like, I suppose if you if you’ve got assets, and you think you look great in a particular, you know, pantsuit or, or a jumpsuit or jeans or something like that, then you know, I can appreciate why you’d want to want to do that. But I always prefer to see, to see a woman in a dress, you know, particularly if it’s early stages of dating, but even when we go out, I mean, I just love that you. I mean, I can’t think of a time, maybe one in 10 times, you might wear jeans, you know, when we go out and you’ll still dress around it. Like you’ll still wear heels or boots, you know, sexy boots and cute tops or something like that your dress around and they’ll still be still be feminine. But yeah, I much prefer to see you in a dress. I much prefer the whole, the whole roleplay You know, it reminds me for the Tony Robbins fans out there. I’m a Tony Robbins fan. You know, he always talks about getting into a state, you know, and that’s a physical thing to do, where you move your body and you create, you know, internal belief that you’re shifting into something else. And I think dressing up is like a costume. And it’s part of that process. Yeah,
Trudy: I agree. It’s like what you said to me, you know, just the other night that we compared it to watching your favorite football game and putting on your football jersey or scarf and you know
Andy: Exactly, exactly. So you know, when you go when you go to the footy. That’s what we call it here. When you go to the footy, we, you know, you put on the colors you put on the scarf, you know, you play the music, you make your friends down there, you know, there’s a tradition you grab a pie, you have a beer is a whole process. That’s part of the ritual of doing and it gets you into that headspace. You know, you’re screaming at the top of your lungs, it’s all part of this process. So if you do it, if you do it for that, you know, the same way that you prepare for work, you’ve got to prepare for the day, you can’t just expect that is going to happen. You know, if you don’t bring the energy, there’ll be something missing and people will call it chemistry. You know, that’s such a word that gets thrown around so much, but it’s usually 100 other things. Not some magical, you know, magic dust that’s not being dropped on you, but it’s about what you the energy that you brought all the other person brought to the space.
Trudy: Yeah, I agree. Okay, next one is to get warmed up with a friend, meet a friend at a bar and have a quick drink with them before your date. This is an interesting one. I really like this one.
Andy: Yeah, well, it’s good because it’s definitely confidence. You know, so safety numbers if you have it, you know, you’re not saying that you’re going to be with them when you meet your date. But just getting into that headspace again, it’s another part of the process, isn’t it? You’re going there, you’re gonna have a drink, have a good laugh, you tell a story. You know, you’re getting more confident and more relaxed. And that energy is so, so important. I think particularly for men because if you feel confident and relaxed, you take up the space and women really notice that.
Trudy: I agree. You know, and look, I think it’s okay, I know that we’ve we’ve said before, look don’t you know, have two things on don’t double book yourself. You know, I mean, like you. It’s okay if you want to meet a friend or family member or whatever first for a drink, and then leave the evening free for your date. You know, because as you say, that’s just helping you to shift your energy and get into that social headspace after a full day of work. And yeah, you’ll feel a lot more comfortable, relaxed, and that’s going to shine through and your date will feel more comfortable themselves. So I just think that’s a that’s a bit of a no brainer,
Andy: It’s a good too, but if you don’t have if you don’t have the opportunity to meet with someone else, doing something you know, we have our favorite like stand up comedians and stuff like that. I can watch five minutes of something on YouTube, have a good laugh, and it can completely shift my energy. So you know, if you don’t feel that you’re in the most ideal headspace do something, you know, it can be really simple. Like you said, play your favorite song and play it, you know, Blair interiors, or do whatever you have a dance, whatever it is, you’ve got to make some sort of physical action in order to shift into the right headspace.
Trudy: Yeah, I agree. All right, the next one, it’s not dress for success. It’s dress for sex. Andy: Enjoy.
Trudy: And it’s not the Roxette song either. I know you’re not a fan, but I couldn’t resist.
Andy: Yeah, and you’re not talking about dressing to have sex, you’re saying dressing for, for the, for the gender for the set for the communication of sexual energy, and all that it’s such a huge part of what everybody loves to call chemistry. Right?
Trudy: Yeah, that’s right. That’s right. It’s just, it’s just being sexy. You know, we don’t want you to turn up and be wearing nothing. I mean, it’s, you know, you could wear something from head to toe and look incredibly sexy. It’s just about respecting the date, your date, the occasion? And, you know, not pleased girls No. activewear Okay. I mean, Andy: I’m amazed, to be honest, that people would know you.
Trudy: Are you?
Andy: Yeah, but what? Well, less when I think about, you know, we’ve we’ve, we go out into all kinds of places from, you know, like the local pub to, to fine dining, and we travel a lot. And I’m, I’m actually amazed at how little effort the average guy will take getting ready for a date. And I’m just
Trudy: Yeah! you often comment on
Andy: That guy. I can’t, you know, that’s what he chose.
Trudy: I know, like a T-shirt wearing,
Andy: You know, some, like a daggy hoodie. And, and, you know, dirty sneakers. And I’m just like, What are you thinking? Like, there’s no, how disrespectful is that to the person that you with? And often when I say when we go out, we see them on a date. It’s not like it’s a new date. Like you can tell that there are a couple
Trudy: Yeah,
Andy: You know, and I’m thinking that’s even worse to me in a way. Like, you can’t drop the ball like that, you know, when if we go to Mr. Wong’s or something on a Friday evening, all the guys are in suits, because of comes straight from the office, you know, but if we go to you know, I’m amazed that we can be out on the weekend somewhere, and we look around and be surprised at how poorly people are dressed.
Trudy: Yeah, yep. That is, that is a fair call. And I know it. Especially if we go to the opera. I know, it bugs you that people aren’t dressed for the occasion.
Andy: Yeah! Of course,
Trudy: very ….
Andy: Or, you know, yeah, absolutely. Just that does bug me.
Trudy: Okay, next one. Don’t confuse your date with a work style meeting. If this is not a job interview or a proposal presentation.
Andy: This one drives you crazy.
Trudy: Oh, my God
Andy: You slammed the phone. at work? Can you just shake your head? I’m like, oh, somebody somebody has given somebody a job interview.
Trudy: And this is like rookie error 101. Please do not turn your date into a job interview. It. I don’t know why. But for some women, they and I’m sorry, girls, but I am picking on you here. But there are some women that feel they need to get all their questions answered on their checklist. They have to know about his past relationship history. what the situation is with his kids or if you want more kids, they want to know all about his work or all about his financial status. And they’re not shy to ask. They will go there, they will go to the heavy hitting questions on the first day. When
Andy: Were they confused? they’re confused about what this event is for?
Trudy: Oh, that’s right.
Andy: Because they’re already moving into the kind of information that you need when you’re deciding to be in a relationship with somebody.
Trudy: That’s right.
Andy: And I don’t know if it’s because of this whole fast turnaround, disposable dating kind of culture, but or what but just that they’re asking questions that that’s that’s not the purpose of the first and second date.
Trudy: Not. You’re so right. It’s not it’s really not you know those questions come later. The purpose of the first day is that it’s just meant to be light and fun. And for you guys to laugh,
Andy: Flirt
Trudy: And flirt and be playful, find out things that you have in common.
Andy: Do I find her attractive?
Trudy: Exactly
Andy: Did she find me attractive? Did I make her laugh?
Trudy: Yes. Do I feel good with them? Do I want to see them again? You know, when we were younger, when we were like, you know, in our 20s. I would never sit down and ask you a whole list of questions about your life and where you were going and what you’ve done. And you know, it’s just never happened.
Andy: Are you cute? Do you make me laugh?
Trudy: That’s exactly,
Andy: That’s enough to start to make an investment and start to explore more.
Trudy: Yeah, that’s enough to then go. Okay. Well, let’s go and date number two.
Andy: Yeah.
Trudy: So that’s what you guys have got to do. You’ve got to stop this whole checklist thing. And just enjoy the moment. Create opportunities for laughter, smile, flirt, be playful. You know, you want them to leave the date going, “Okay. Well, I had a really good time, I enjoyed that person’s company. And I want to see them again”. That’s it. Not, I know everything about their life plan, and their date history. And we’re going to talk about this a lot in other episodes, because it really bugs me some of the things that people think it’s okay to ask on a first date. And I do just want to leave you with one extra tip about that is that don’t be afraid to not answer a question on a date. Don’t be afraid to go. Look, ”I don’t think we should go there right now. Let’s talk about that on date number. You know, not even– date number, whatever. Let’s just talk about that another time”.
Andy: Yeah. So how did you and your ex break up Trudy?
Trudy: Yeah. Look,
Andy: Oh God!
Trudy: You know, let’s not go there. Okay, let’s talk about that another time. You know, it’s, it’s just not appropriate. Don’t be afraid to pull the reins. And if they go off track, to bring them back on track and say, “No, let’s just stay in this nice, safe, fun, flirty space for now. Nothing too heavy or serious”.
Andy: Yeah. Yeah, I think you said that you were different than to talk about this a lot. It’s a huge topic around the office. And Lisa, who’s a psychologist. She said, You know, people just get the dating and relationship parts confused? and understand that they’re completely different processes. And this time, you know, it’s all about, do I like them? Do they like me? And your role should be to walk away and have them go? I’d like to see that person again. That’s right. That’s it. That’s the only goal. That’s a goal to kick on that first day.
Trudy: That’s it. So look, I think that we have absolutely covered this topic. I think we’ve we’ve given some really great tips on how to get into the date zone,
Andy: And move away from any other space, or we’ve used work for the example for this, like getting out of the work zone. But it could be anything. It could be if you’re, you know, heavily commitments with your family. Or if you’re, if you’re more mature and you have kids from a previous relationship, and you look after them, you still have to step out of that space to get into the dating space.
Trudy: Yeah, that’s exactly right. So yeah, we would love to hear any feedback from you if you have any. Again, we would love any suggestions if you have a topic that we’d like to cover and that you’d like for us to cover in another upcoming episode. Thank you for joining me today, Andy.
Andy: Thank you very much. Don’t forget to have a chat with Trudy on And you should tell them about you know, remind them about the quiz.
Trudy: The quiz. Yep. I was just about to cut me off.
Andy: Typical.
Trudy: So yes, go to and there is a quiz you can do to find out if you are ready for your dream relationship. It’s only a few minutes. And I think it’ll give you some insights into the headspace that you should be in and maybe also shine an area on things that you might
Andy: Might need to focus on.
Trudy: Might need to focus on. Exactly. So thank you for listening. We hope that you have enjoyed this episode and you found some value in our tips. And we look forward to being here again next week.
Andy: Thanks for having me, Trudy.
Trudy: My pleasure. Thanks, baby.
Andy: Right Thanks, guys.

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