Women Starting Over in Dating

Starting over is never easy, but it is always necessary if we want to change or grow in our lives. I had a conversation with Cindy Drummond, the author of Reflections of the Dating Pool, about her journey to start over after a shocking discovery and the road to support other women. Cindy is also the creator of Women Only Weekend (WOW) events and co-host of Words of Wisdom online gatherings.

Part of her journey was about “start before you are ready” where she went on 50 dates in a year in search of love. She turned those dates into learning lessons and part of her healing process. Eventually, it becomes her book with words of wisdom about loneliness, the importance of finding a tribe and how she fell in love again…with herself. Cindy lives in Canada and is now married to her loving husband.

Interview Highlights

Background story and how she “start over”

From a healing process to writing her first book

Why 50 dates and what she learned from that experience

Dating takes courage, compassion and tenacity but it also brings opportunities to fall in love with ourselves and others

3 tips for navigating the challenges when we “start over” in any areas

Word of Wisdom gatherings – why it is so powerful for women to connect and share stories

If you would like to find out more about Cindy, her book and in-person and online gatherings, please go to her website CindyDrummond.ca

Video

Transcript

Sze Wing (00:03):

Hi everyone. Today I have Cindy Drummond to connect with me here on this podcast or video if you are watching on YouTube. So I’m really excited. She’s all the way from Calgary Canada. So welcome Cindy.

Cindy (00:19):

Oh, thank you so much. I’m very excited to talk to you today. Yes.

Sze Wing (00:23):

So a little introduction. So Cindy is an author. Her book is called “Reflection From The Dating Pool” and she had a very interesting story to tell us regarding the book. She has a fascinating story and obviously a truly empowered woman. She’s also the co-host of a Sunday souls gathering, and I love it. So, because this gathering is Words of Wisdom and she also run this really amazing weekend gathering or retreat, whatever you want to call it, for women called Women Only Weekend, which I would love to attend, but obviously it’s in Canada and we’re in locked down in Sydney, so I can only dream. But what I find is so amazing and why I really want to talk to Cindy today is that she obviously had gone through some things in her life. But she managed to really come out strong and now running these events that, I feel we are very needed to connect with other women to empower each other, to listen to each other’s stories. So I’m really excited to interview her today and I hope her story and wisdom and advice can also help our listeners. Welcome to my show.

Cindy (01:46):

Thank you.

Sze Wing (01:47):

So, first of all, for those that don’t know, actually now I’m recording during a mid-morning in Sydney, Australia, but it’s 7:00 PM like evening time for Cindy, but she’s still enjoying daylight. So we are very envious as it’s pretty cold. So I think first of all, I really want you to tell us a little bit about yourself, your background story, so to speak, let that lead you to write your book “Reflections from the Dating Pool”. So yeah. Tell us a bit more about it.

Cindy (02:20):

Thank you. Well, so where do I start? I guess I didn’t plan on writing a book. I always sorta thought about writing stories. That was interesting to me, but I didn’t have, I didn’t have a topic to write about. I was just living my life. I was busy raising my children in my thirties and early forties and men. I went through like many people. I went through a traumatic time in my life. And even then, I didn’t know I was writing a book. I was just trying to get myself through the experience, but as I was doing that, I was making notes and I was journaling and I thought I was talking about my story and going through it, people kept saying, oh my goodness, like this would be a really good book. And so I, at some point after, I’d gone through everything, I realized that maybe there was something for me to tell people and a story to share.

Cindy (03:19):

So that’s how the book came about. We won’t give too many spoiler alerts, but my story again, maybe not different than many people. I had left a marriage and I entered into another relationship and it was about a five to six year relationship. And it ended abruptly one morning when six police officers came into our house and took the fellow who I was living with away in front of me and my daughters, in handcuffs. And I knew at that moment I needed to start over. And so I, within 24 hours, I’d moved into my parents’ basement rock bottom. And I knew that people were worried about me. I was worried about me and that propelled me. I think also being a mom and having these two girls that propelled me to set a new course of action for myself because I knew they were watching me. And I knew what I did next was going to be very important.

Sze Wing (04:25):

Yeah. So that was really the beginning of this new chapter. Isn’t it? Because I have read the beginning of the book where it sounds like suddenly, like from a happy normal Monday shattered into something, you know, completely different. And what I was thinking when I was reading ,is that, as a mother, myself, my daughter is only four and I have a son who just turns one, but I imagine I’m a Leo. And I felt I’m a lioness when it comes to protecting my children. Because obviously there’s a million things go through your head, like related to your relationship about the man you were with, that it’s always about our children, because we want to model for them. We want to protect them. So your instinct will be “what I’m going to do next” and how I’m going to react and respond to their situation, which I think it’s so helpful to think about, retrospectively it’s all about how we respond to this.

Sze Wing (05:22):

And the more we we know ourselves, we are more resilient with become a more empowered, become like how you come out of this tunnel, that we actually are better in terms of how do we respond to this kind of threatening situation. But so going back to that topic about, , what I wanted to share with you is that, you know this person for six years and then suddenly this happened to you, you were surprised that he know you see him one minute in pyjamas, next minute in handcuffs. But were there signs before that you think, oh, I wish I would have paid more attention to it because the reason why I’m asking you is that I also had a dysfunctional relationship for about two years. And when it finally, and they’re not as erupted, but pretty much it was just kind of me discovering, he hasn’t been true to me and so forth, but retrospectively there was signs and red flags. I mean, what do you think about that now?

Cindy (06:27):

For sure. In the beginning I did, because you have so many questions and when you’re in something, when you’re deeply involved in something day to day, you don’t have the ability to step back and see it from an outsider’s perspective. So yes, there were signs, there was those whispers in your gut that you knew something wasn’t adding up, but you also didn’t want to put a name on it because you didn’t know for sure. So you start this cycle of doubting yourself and you start the cycle of not trusting, but then any answer will make you think, okay. Right. Like it’s, I’m probably wrong, you know, because when you’re with somebody who is good at lying, it is good at pulling the wool over people’s eyes, you start becoming the person who’s crazy. And so you start really doubting yourself and it’s not until they’re arrested in handcuffs and you’re removed from the situation or they’re removed from the situation that you’re just like, oh, I wasn’t crazy. I just didn’t trust myself. Yeah.

Sze Wing (07:40):

And I had the same thing. Like even to the extend that I saw something, a text message, I probably wasn’t meant to see. And I was like, what’s this about? And the respond was, how could you peek at my things and I was being accused. You know, the response often was that they defend and attack saying, with all the red flags, if we voiced the red flag, immediately would be asked that you should trust me or what’s that behavior? And then you have self doubt, right. Women often are very intuitive, but the same time we try not to necessarily pointed out these things. So we took a step back, but I knew we could fast forward. So obviously you put your life back together. What was really interesting is that it, you have this sort of experiment where you’re going on 50 dates in a year or something. And then, see what happens because I also relate that there was a period of time that I felt I was dating a lot of people because came out from that relationship and I wanted to move on. Right. And then there was also a period of time that I just decided that this is a deep freeze. It’s a winter for me. I’m was not with anybody for a long time. And it actually taught me a lot of things. So tell us about your dating experience. And

Cindy (08:55):

That’s a really good way of putting it. So we know that I didn’t start dating immediately. I first made sure my children were safe and made sure that I was moving my life forward without the dating piece. And developing friendships with lots of other women and sort of finding my tribe. And then when I had the confidence from that, that’s when I decided, okay, I knew I wasn’t ready. There’s never, maybe you’re not ready to date, but I knew that if I “wintered” using your expression, if I “wintered” too long, then maybe I would never want to date again. Or maybe I would be too scared to date again. So I kind of wasn’t ready, but I was sort of ready. And that’s why I said, okay, 50 dates, I’m going to go on 50 dates because that was a time I need to also heal myself.

Sze Wing (09:51):

It’s amazing. Like people was like often very cold feet, maybe try one or two. And then Cindy goes I’m going to connect to 50 just to test this theory out. I love it. So tell us a bit more about that experience, what that taught you, what you have learned from it. And perhaps, probably I’m compounding too much in this question, but what other people could learn from you if they’re really scared?

Cindy (10:19):

Well, one is, I can relate to that. I was very scared. I drove to my very first date with tears streaming down my face. I was so frightened and I was so scared about trusting again, but what I learned through the journey and by doing it is like I started giving myself words of wisdom when I was journaling. Like if I went away on a date and somebody only talked about themselves, that I would come back and I would remind myself, okay. So make sure that when you’re showing up to meet these people, that you are being interested, that you are taking the time to get to know them as well. It’s not just show and tell who I am and why I’m so great. It’s also about learning how to listen be an active listener.

Cindy (11:07):

Andsome of the other things that I learned is that I wanted to make sure that I didn’t trifle with anyone’s feelings. You don’t know the other person, what they’re experiencing when they, you know, not everybody is scared to date, but I’m sure that men are also putting themselves out there. So I would try to be respectful of what their feelings were. I didn’t want to hurt anybody unnecessarily, but I also have boundaries. It’s a compounded answer as well as your question because there’s a lot. And that’s why I think, you know, the journaling piece, again, you’re writing down how you’re feeling in the moment, but then you can reflect back and see, okay, how did I show up that day? And how did I show up, what I’ve reacted different if I’d had a better day at work. So there’s all those things that are going on.

Sze Wing (12:00):

Well, Cindy, you’re truly a top grade A student in the universe eyes because you take all these 50 days into 50 learning lessons because you know, this guy talking too much about himself, you write down as it, not like judging that that’s the fact, but more like, what can I learn from it each time? Right. And how am I going to show up when my next date? So 50 actually instead of 50 dates, there are 50 learning lessons that you decided to take yourself through. And I’m sure like there are ups and downs good and bad days. So some turns out better. Some was just ridiculous. I’m sure, but when you have that attitude, as each of these are learning lessons or an encounter for a reason, like one word of wisdom, it’s probably justified this occurrence, it just make you so much further on this path.

Sze Wing (12:57):

Then you know, where you start and whether or not you actually like for those people who are listening, they may be thinking, maybe it’s a number game, by 51 then I will meet someone, but even forget about that outcome by detaching the outcome, just thinking how far you have gone. If you look back as your personal development or just personally healing, that’s tremendous. So Bravo to you, Cindy great A student. And it’s true. So maybe tell us one of the most remarkable or ridiculous or funniest dates, like just to keep those who are really scare on the sideline a little bit of a “Oh, that could be cool.”

Cindy (13:40):

Well, I do remember going out on one date and we were chatting and we were talking about both of us where we were on our dating journey. And I remember the person saying to me, well, how do you handle it? If you meet somebody and you know, they’re not your type. And I had an answer right away. I was like, well, like you can always need more golf partners or people to go bowling with her, whatever it is, it doesn’t always have to lead to romance. And he kind of nodded and we finished our date and then when we were leaving and walking out the door together, I said, well, that was great. And he said, yeah, we should go golfing sometime, which immediately just put me into the friend zone, but you know what that is. Okay. There, wasn’t the going home and like wondering. I love that actually. It was just like, yeah, absolutely. We’re in the friend zone. We can golf some time. Yeah.

Sze Wing (14:41):

And that’s go back to, I really feel that recently. I do talk a lot about whether its my video or podcast when we’re so attached to outcomes. Sometimes we’ll fixated a picture because can you imagine, just because you have done this 50 lessons, you are a very different person from the beginning. So the person you attract to you, it’s on very different level. You will end up in a much different story if you were grasping tightly like that, I should get somebody by the 10th date. And then you kind of missing the whole point. Isn’t it? It’s sometimes we can take, we definitely should take action. You’re going to leave the house. You go to, you know, do what you feel inspired to do, but inspired to do rather than, oh, I’m going to just do this 10 dates. So 20, 50 days tick the boxes and bam, I want this outcome. I think that pushing and forcing thing is not, doesn’t usually yield the best outcome. And I think having that attitude demonstrates it with that date. It’s so cool because you don’t know, maybe through this friend, you meet his friend and so forth and sometime we also need good friends are frank and genuine. And he was very genuine in terms of asking you that question. So that’s fantastic.

Cindy (15:57):

I thought it was fantastic. And again, just some of the things that you said really resonate, because imagine if I drive to my first day crying, I’m obviously not ready for a relationship. So I wasn’t showing up as the best version of myself for those first few dates as I was figuring out. So if you’re willing to do the work on yourself while you’re learning how to date, you’ll be the best version of yourself possible through experience and through practice.

Sze Wing (16:29):

For sure. And so before we, I have a ton of question to ask, but before we move on to next, I want to ask, what would you say to someone who may have a horrible story or still healing? Not sure that if they’re ready. What would you say to this friend, this girlfriend of yours too, you know, maybe take a leap of faith or how do you approach a slightly differently?

Cindy (16:54):

I was thinking a lot about that. And I think the first word, words of wisdom or the advice that I would give is you don’t have to wait till you’re completely ready or healed. You just need to, it’s like when you have, when you’re training for renew training for a sport and you hurt yourself, you obviously go to physio and you do all those things, but you slowly venture back into the sport because you know that what you want to attain at the end, right? So you, you do, you do maybe start before you’re completely ready and you be kind to yourself and you know, that you’re practicing and you’re getting stronger. You’re getting better.

Sze Wing (17:39):

Yeah. I really liked that. So moving on to the next part from having all this, to writing a book is an other leap of faith, right? I’m sure a lot of listeners here have the stories, have the experience. And it’s, for me having written a couple of things, I think in some ways it’s very therapeutic. It’s very healing. And if you know what you’re writing and sharing, it’s going to help other people. You also feel you’re doing something meaningful. So what’s your experience and why did you take the leap of faith and the overall what you have learned from publishing this book?

Cindy (18:23):

Well, you, you touched on some of those as well. So when I wrote the book, I didn’t have any expectations. I knew I needed to write the story for myself. And if not, one person was interested in reading my book, that was okay because I was the audience I was writing for, as it turns out, my story did resonate with people. And I know, I knew this before, and I know this even more clearly. Now we all have a story to share. Not everybody needs to grab a pen and paper or pull out their computer. But I think through sharing again, there’s wisdom and learning. And so I think that if people as a society, we are getting better at sharing our stories. But I think that if you don’t want to write a book, but you want to go join a storytelling group, or you want to even go into like counselling group sessions where you can be talking about what you went through, because everybody has something to share. And everybody has words of wisdom that they can pass on to other people. We think that we are so unique and yet we share so much common experience.

Sze Wing (19:38):

Yeah. And everyone has a different way to articulate or to look at the story as well. I remember this author, Christian Northrup in her book Make Life Easy. She shared one particular technique about emotions. I hope I record this part correctly, that people will be sitting in a circle and they will talk about the story or whatever they’re holding on strong, emotional attachment or reaction to it. And then people who are listening, I think the left of that person would talk about what kind of emotion the story brings out. So the person, like who just told a story person to the left of that person would say, I hear , say sadness or anger or frustration, then did the right hand side person will say, well what the person needs, whether it’s time to heal or a time to cry, opportunity to release. So, but they have given, I mean, nobody is saying this is correct or wrong. It’s more about other asking other people to share the perspective based on the story, what they could hear in terms of what kind of emotion came up, what kind of need is this woman needs at that? She may not know herself because she may know I’m angry, but she may not know I’m jealous or she may not, I need to heal it, but she may not know she needs time and permission. I thought that was really interesting because when you talk about that, I think that brings up opportunity in a space for women to do that right. When you share stories. So you’re smiling.

Cindy (21:16):

Yes, because again, at the time when I was creating my women only weekend, I didn’t purposely set out to achieve that, but that’s what it became. It became a community of women that could gather and share stories and learn and empower themselves. So I do think and you know, one of my favourite books is Anita Diamonds, the Red Tent, and it is all about from a it’s not a religious book, but it is because it talks about, the women back in the time of Jesus. And they’d all go into the red tent at a certain time of month. And, you know, they would tell stories and they would take care of each other. And I feel that we’ve lost some of that. So any opportunities where we can come together as women and share, I think is amazing.

Sze Wing (22:05):

That’s exactly it. So that’s perfect. Cause I want to ask you about, obviously the listeners or viewers may not be in Calgary, Canada. So they may not be able to join those weekend, which I’m also love this kind of women gathering because I think when women gather, magic happens, whether you sharing story or you sharing tools and techniques. It’s about empowering each other and spending time for ourselves, which we rarely do now, because it’s all about looking up to everybody or chasing a career. But sometimes we kind of need to step back, go back to who we are, what we need first, before we go power out. So a lot of people may not be able to join you on the weekend, but you have the word of wisdom, Sunday gathering that soon coming back in September. So can you tell us a bit more about that?

Cindy (22:53):

Yes. So that came truly out of being at a pandemic shortly after the first lockdowns in April of 2020 I realized that I was missing connection. And so I asked a friend if she would be interested in doing these Sunday weekly one hour meetings. And of course she was very interested. So every Sunday from 10:00 AM in Canada to 11:00 AM, we would have small groups, but sometimes people from all over the world and we would have a presenter. So we would do little bit of grounding, little bit of gratitude, like maybe writing a gratitude letter and then just have a speaker talk about something. And honestly it could have been anything from meditation, but it could have also been finance or anything. And it just was that hour to bring us together. And she’d be looking at each other through a screen, I guess, but just again, that bond that gave us a place to share. And so many of the participants were there every Sunday and that was, they’re like, okay, I’m a busy mom, but Sundays at 10 o’clock I just grabbed my coffee and I, and I sit down or, you know, some ladies were joining from England. And so it was the end of their day and they were just getting it. That was how they were finishing their day with a little bit of grounding and gratitude. And it just was this beautiful one hour. That’s all we needed to connect. Yeah.

Sze Wing (24:23):

Yeah. So for those who are listening and interested to maybe grab your coffee on a Sunday, if you in the right time, so, or a cup of tea at the end of the day, if you’re on the opposite spectrum in time zones. So you can check out of this at Cindy’s website, which we’re going to out on the show notes later. And also I’m going to ask, but before we wrapped up, I really want to ask you out of doing the book and all these gathering, and these event with women, what do you see that, things that you see that we all really need, but may not be giving ourselves enough? Or what do you see that could be something that we should be reminded of as group of women, since you have been listening to all the stories and having all this time with people.

Cindy (25:15):

That’s a really good question. I think that again, we’ve, we all are having these different experiences with what’s been going on in the world, but I think that, so there’s been a lot of fear for some people. So I do think that take a chance if you, if you’re feeling lonely and isolated, reach out to at least one person or a group or find, find a support system online, like words of wisdom or go to an event, even if it’s, even if it’s an outdoor event in your community that you can attend with other women, like look for those opportunities. Because I do know personally, a lot of women that feel more lonelier than ever right now, and that breaks my heart.

Sze Wing (26:03):

Because of the pandemic life, for example, I don’t know how it was in Canada, but at the moment we have sort of the second round of lockdown this year and Sydney in particular, we are like, a couple months on, we are halfway through I think and I was reading up about this single bubble, they call it. So if you live alone and also within depends with district because there are certain area you can only have another visitor within, but this single bubble thing really makes me think that, can you imagine in the lockdown, you work from home if you manage to have work at all and you are so alone, that’s a really challenging time because women love to be together and share and connect. And this is the time really testing our endurance and testing our, our courage to do things that help us. So this is like, you said, like fear and feeling lonely, it’s one of the biggest thing. I think there are things that people can try out to see what it’s like for themselves. Maybe some people really will enjoy online dating or, joining internet groups, but they won’t know unless they try. Right.

Cindy (27:26):

Exactly. And I think you’re right, like this maybe is a good time to dabble in online dating or find maybe there’s an online speed dating group or maybe there’s even if it’s, even if it’s not, you know, dating, but you know, look for online book clubs or just do something so that you’re not, if you are working, that’s awesome, but you can’t just be working and on social media all day, you need to find ways to connect.

Sze Wing (27:55):

Yeah. And I think the topic of starting over, it’s also a really big one for a lot of women because you know, it could be a new job, could be a new relationship or could be coming up in pandemic. That’s the theme, the recurring theme of starting over. And it takes a lot of courage to actually do it rather than stay in the deep freeze, the winter. Because when we choose to stay in the winter, it felt like we’re not starting over because starting over is so scary to so many people, they rather than stay in the deep freeze. So, but, and you know, a lot about starting over, you have done a few. What would you say to your younger self that you about to say, well, what would you say to that person?

Cindy (28:41):

Well I guess when you say my younger self, because I have two daughters who now are 25 and 22, so I was encouraging them during a year and a half of lockdowns on and off. And just saying, I actually, I’m going to use the words of wisdom from my youngest because she was going to school full-time. So again, she’s in school, in her room, her job’s in her room, she’s exercising in the house and she said, you know, I need to come out of this pandemic with a passion. And so she took up snowboarding, which was something that she was, that we were still allowed to do. We just finished winter. She was able to go snowboarding and she was still able to do so. She was looking for things that she could become passionate about, I guess, making lemonade out of lemons when, because it is scary. But imagine, imagine being 21 years old and your life has completely shut down, you’re not going out to see your friends. You’re not at school. And so I think she’s a bit of an inspiration, she doesn’t have maybe the baggage that some of us might have at an older age, but she, she was living her best life.

Sze Wing (29:56):

I’m pretty sure she learn from example. I mean, the way you talk about your 50 dates like it was just wonderful 50 lessons, because some people will beat themselves up as one for 48 and see why I got another, I found a really interesting way to mention your daughter that again, turning this into something to reflect within ourselves because she wanted to come out of this with something like, and I think it’s really inspirational because we can or dwell in this. We can, you know, go crazy on online shopping or video games or all that kind of stuff, addicted to being another reality because we don’t like this one, right. That she turned into, let me figure out what is, what is my next project or my passion, so I can do it and channel this locked up energy.

Sze Wing (30:47):

And that’s really, really great. And passion may change maybe in a couple of years, snowboarding is not necessarily going to be her profession, but she may be interested in, I don’t know there is no skiing in the summer. Right. So, but as you said, make lemonade out of it, it’s a really useful thing. And rather than turn into, you know, dwelling into this spiral of doing horrible things, like I do think watching too much Netflix or on too much online shopping, or, you know, finish your video games and it’s not necessarily the best way to get through it. I think people would need some of that, but be mindful how much you consume it, how much it consumes you.

Cindy (31:37):

And I think that’s totally fine if you want to spend a weekend watching Netflix, but again, be, be present and mindful that that’s what you’re choosing to do that day. So make sure that if it’s a Netflix day, that’s your choice. Right. And if it’s okay and that’s okay if it is your choice, but maybe then, then the next day, maybe it’s, and again, it’s so hard when you don’t know what all the rules are everywhere on the world, but, you know, five sit-ups or, you know, like jogging and like, whatever it is just be kind to yourself, but, but always know that you have choices to make and those choices are okay.

Sze Wing (32:19):

Oh, could be watching any video or podcast like this to get you more uplifted because you may consume half an hour of this interview. But if the next thing you may want to do is to sign up for online dating or sign up for online gathering group or a goal and see what kind of outdoor sport you can try. Like then the choice is also up to you. So you consume also matter because it could inspire to do something more positive. But anyway, I love this interview and I thank you so much for joining me tonight, today. And so for people who want to connect with you say maybe join your online gathering or if they are in the area, they can come to you your women only weekend, or if they want to buy your book, what’s the best way for people to connect with you?

Cindy (33:08):

I think the place that points them to all of that is my website, Cindy drummond.ca. You can buy my books off Amazon. You can register for the next words of wisdom, which will start in September. Send me an email. Tell me your story, ask me for advice. I do think that I’m always open to support and hear other people’s stories.

Sze Wing (33:30):

Thank you so much. And I will put the link of your website on the show notes, and obviously we’re going to share this on social media and you can follow and connect with Cindy there. So thank you so much for this time together. And I’m so excited for you, because you guys now can do things. So thank you so much.

Cindy (33:54):

Thank you.

112. Women Starting Over in Dating: Interview with Cindy Drummond

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