It's night with Dan Ray. I'm Delli Fleas, Boston News Radio.
All Right, it's Valentine's Day night.
I hope all of you have had a wonderful Valentine's Day. It's that day during the year when all of us focus on our love lives and whether they're satisfactory to us or whether they're not. Some Valentine's days are good. Some Valentine's days are not so good. And with us tonight to celebrate Valentine's Day and the release of her new book, Shot at Love is Boston photographer really an extraordinary person and a friend of mine.
I'm a friend of their families.
The Brett family of Dorchester who produced these fabulous photographers, and certainly right there amidst amidst the best of them is Carrie Brett. Carrie Brett, welcome back to Nightside.
How are you hi? How are you happy?
Valanin Times day and yeah, well for you right now it is it is a good Valentine's Day. And uh, but it has been a very interesting journey that you have been on. You're an award winning photographer. Uh, You've You've done photo shoots with some very big name celebrities. You've you know, shot for uh Boston Common magazine, the Globe magazine for many years. You were the chief photographer for The Improper Bostonian, which many of our listeners will remember.
You also now have a top rank dating podcast, and that dating podcast.
Is really what we're going to talk about tonight. And the book that has.
Come out of that dating podcast is today, the day the book actually has been been released.
The book has been live on Amazon for ten days with a push for the launch of Valentine's Day. So we did a short press push to celebrate Single Awareness Day, which singles call Valentine's Day because on Valentine's Day, it shines a light on the fact that you may be looking for love or you might be unhappy that you're alone,
and it can be a hard day. So sure, Valentine's Day was the first with the launch day of my show five years ago, and I thought, wouldn't it be great to launch the book on the fifth anniversary of the show.
Yeah, you were in a great relationship at this point, but you had some rough Valentine's Days over the last few years, correct, And that's.
Part of the book, right, I had a lot of lonely holidays and sad Valentine's Days. I have a hard time with holidays in general, and I think it's because I had so much hardship when it came to the love department. And I'm very mindful and empathetic to those who feel left out or alone or have lost somebody. And if you've lost someone that you've loved, whether our relationship is ended or that passed away, it can be very trying. And I wanted to create a movement in
a community for people to feel less alone. So that's what I've done with my show.
Yeah, and the podcast is going well as I understand it correct, It's gone great.
I love it. I love every minute of it. I bring the most amazing people into my life. The episodes that I produce are fascinating to me. And I say all the time that I think I created the show. I created the show for people who were struggling and people who are having a hard time on dating apps because I was one of those people. And and in the end, I think I actually did that show for me because it's so rewarding. It makes me so happy that I can help people.
Well, let's I want to talk about it and it's it's interesting you you disclosed to me the other day that there came a point in your life where you were working and your your relationship fell apart. A lot of people have relationships that fall apart. And I'm sure that first Valentine's Day was tough. Your birthday also, as I understand, is February eleventh, so you could have sort of had the double whammy, if you will, of a few tough birthdays backed up by some tough Valentine's Days.
Tell us some just just you know, sketch out the story, and then I want to sketch out all the people who you have interviewed, who you have photographed, and what lessons you've learned from this entire experience.
Okay, so let me take you back about twenty years ago. My marriage was falling apart, and I had a one year old and I was getting divorced, and I went through a three year custody battle that was very difficult, and I found myself dating with a baby on my hip, pre dating apps or cell phones or texting or any
of those things. And then I was in a long term relationship for eight years and the bottom fell out of that suddenly as they do, and I had one of my very young photography assistants decided to put me on Tinder, and so I became an early evolution dating app user of Tinder, and my whole world opened up. And little by little, by using the dating app, one swipe and one day at a time, I rebuilt my
life back and slowly rebuilt my confidence. So where I was struggling was that I was a successful person on paper. I was a business owner. I had a high pressure job photographing covers for the leading leading city magazine, and I had no information and I was I certainly couldn't tell anyone what was behind the lens of my life, and I desperately tried to help myself, and I couldn't
because I didn't have any strategy. But I did have this little device call Tender that changed everything for me and Jerry.
Was there not a period of time when many people were certainly you know those so sort of dating apps had just come along, But it wasn't something that you were going to probably advertise that you were on Tinder.
Wasn't this sort of a stigma at some point attached to that into It wasn't something that you would be advertising.
I'm on Tinder right well.
Right, No, certainly not as a single mom living in Hingham. I think I joked that I was probably one of the only people at the time because it was new and so people didn't know anything about it. But also to get divorced with the baby back then was also difficult and not the norm, and so I was a trailblazer in that sense. But that was my reality, that was my situation, and I had to trail a.
Tough trail to blaze, to carry it is it is.
But I wasn't afraid of dating apps. I made my own decision. I listened to my intuition and I had luck there and I liked it, and I had a lot of luck because I don't think I had a lot of competition because there wasn't a lot of women in my age at forty three on it. And then I also knew that online dating with marketing and branding at its best, and that was something that I was an expert in. And so God, do you have a question, jam.
Yeah, yeah, In other words, is this part of the book?
In other words, that you've written this book to basically give other people who find themselves in a bad situation that has that has either disappeared or as you say, the bottom.
Has fallen out.
Is part of this book to basically show the world, Hey, if you can do it and you can pull yourself back into a better place, other men and other women can do it as well.
Right. So originally that was the first idea of the original concept of a book, was that, Okay, I have all this information that I've learned about online dating, but then it would be kind of I'd be talking. I would be teaching or preaching or something like that. And I'm a big fan of the Chicken Soup for the
Soul series and Jack Canfield. No, Jack Canfield was a teacher and before he was a writer, and he realized that how he taught his students was he would come up with these elaborate stories and then he could teach teach his students through these elaborate, elaborate stories. And I always felt that I was that my father was exactly like Jack Canfield. I mean he holds corner Duncan Donuts
for two hours a day telling stories. I mean he just I know where his schedule, where his hit his setlist is every day because wherever he goes there's a large crowd, And because I'm justlike him and Irish and love to tell stories, I had all these wild tales about dating, but they spanned over twenty years and it all happened in the city of Boston, with the background
being the magazine. So I had all these fabulous characters and subjects who were my friends that lived through all this with me, And I thought, well, this is a Netflix series. This is something really entertaining, so you don't have to be looking for love to love this book. And a lot of people don't really know what to think of me, I think, and they put me in
lots of different boxes and lots of different categories. But the truth be told, more men listen to my shows than women, and more men are fans of this book so far. Divorce men love it and they desperately need help as well as women, so I help both.
All right, well, let's do this.
I got to take a pause on that positive point, and we will continue our conversation and if people would like to compare notes or ask questions, Carrie's going to stick with us.
For a while here.
I hope we stay talking about this until eleven o'clock it's Valentine's Day again. I hope all of you are with someone you love. If you're not, fear not, there will be other Valentine's Day, and there will be days, and it will be other Christmases and other birthdays and all of that, and not everyone is lucky in love and able to fall in love with their high school sweetheart and remain married for seventy years till death do
you part. Most people go through these days that these statistics, statistics tell us at least one divorce, maybe more, and certainly many breakups along the way. With us. Carrie Brett an award winning photographer. She's the lead photographer of a magazine that many of us missed, The Improper Bostonian. She has shot photographs and pictures for just about any journal that you could imagine. Her new book out today, Shot
at Love, a Memoir by Carrie Brett. She kind of just tells the story of being as as she said, after hitting rock bottom. She became an early adopter of dating apps at age forty three while balancing life as a single mom. She has this podcast, she has this book, and I'm sure she'd love to chat with you. Six ten thirty six thirty back with Carrie Brett talking about
a shot at love on Valentine's Day. Uh. And if you're out there and you need a tip as to how to get back on the circuit, how to get back in the game, Carrie's here.
We'll be back right after this.
Now back to Dan Ray live from the Window World night Side Studios on WBZ News Radio.
My guest is Carrie Brett, an award winning host of Top Rank Dating podcast Carrie Brett. Carry, you are out on as a single mom. You were out dating for how many years be found before you found the actual love of your life who you've been with now for some time?
Yes, about on and off for about two years, because I kept going back and I also so, so the relationship had ended, but I had a couple of more times that of the back and forth. Yeah, and then I I was in short term relationships, which I found myself having these back to back short relationships. And throughout all these failed relationships is where the learning and the growth came. And I didn't know it at the time that I was becoming the person that I was supposed
to be to pull in the right person. So I had to pull in the wrong person and have all these no's to move towards the U s.
It's kind of it's a tough story.
Are you still in touch with your former husband with whom you had.
A child?
Well that was that story is twenty That story isn't in the book because there's other stories, and also it's the father of my daughter. So I decided to okay to leave that out, you know, for my daughter, which was understandable. But there's plenty of unbelievable stories in there that touch upon But I think a lot of people, a lot of single people go through.
Well I want to get to those, but before that, just to get you in focus and in context, here give us the names of as you were going through this, you were you know of of this, this, I don't know what you want to call it, journey, this search whatever. You were in your in your job, in your profession. You were meeting and photographing some very exciting celebrities as well, and you you learned What did you learn from from
those celebrities? I mean they we see the celebrities and you assume that their lives are all perfect, But you get to spend a lot of time with a lot of these celebrities, and I assume that you came to realize that their lives were not perfect.
Well, I don't think there's any person who goes through this classroom really, which is what I call earth. This is not supposed to be heaven. We're supposed to learn and the struggle is may look different for other people, but people struggle through all sorts of heartbreak and all sorts of challenges. And when I photograph people, I can cut away all the exterior and see their heart and see the type of person that they are. I'm not
friends with all the celebrities that I photographed. I may have not clicked or connected with them in such a way. But the people that are in my book I did, and I was huge fans of and because of the kindness and the generosity that they had within their hearts, they helped me along the way. And you know they say when a window closes or a door, you know whatever, the saying is that someone will show up.
And be that one door closes, another door opens. I'm very fooliar with that, and I've experienced out in my life. Let me ask you this before we go to break here, just give me a list of some of the celebrities people will meet in this book.
Shot at Love Sure, So we start with my best friend, the Wing Girl, another single mother, my friend Kelly Doyle, who we can't do this with our friends, so she's the first friendship. She gets married long before I find love, but she teaches me about worthiness and if you don't have worthiness, then you're not You're certainly not going to find love. And then I take you through the different people that worked with me at the improper celebrity writer
Jonathan Sorov financer and celebrity writer John Spooner. These were two guys my publisher, Wendy Simonian epic. She marries the general manager of our magazine, our local digs. He definitely dug Wendy and they got married at that wedding. I meet someone who didn't know it at the time while I was single. I would find I think twelve or fifteen years later on Tinder a lot of so some of the celebrities, Chris Cooper taught me some valuable lessons.
Steve Carell, Tim Wakefield. I photographed a lot of Red Sox players for twenty eight years every year for the Red Sox Edition issue and Tim was someone that I connected the most with and he helped me every spring season and it was just a really kind person, great great man. Lucky to have known him. Let's see my mentor,
Jeff Lubin helps me with my dating breakthrough. And then I date a whole cast of characters that their names have been changed and their identities and all that, so you don't know who they are.
You also, by the way, have a pretty good relationship. I recall with Bill Belichick.
Well, Bill, it was always very good to me, very kind to me. A photograph him twice for two covers. And Julian Edelman is in the book. He is He's that scrappy player who, oh yeah, I align with because he had the determination and the grit to to do the I mean, he his mind just shows that he was told no. I think a lot of these celebrities were told no throughout their career and that made them kind of feel sorry for me because I was being told no. Not at the magazine, but I was being
told no through dating, and so that's that's what happens. Though.
Let me take a break. We've got to We've got a newscast coming up again. Feel free to join the conversation, folks. This is Valentine's Night. My guest Carrie Brett. She's an award winning photographer and host of a top rank dating podcast, and her book Shot at Love is a memoir of her life, which has been in many ways an extraordinary life and also in many ways a similar life to what most of us have lived, ups and downs, as many ups or as many downs, as many ups, and
she kind of bears her soul in this book. And if you'd like to chat, we got some numbers for you six one, seven, two, four, ten thirty or six one seven, nine to three, one ten thirty. Back on Night Side with Carrie Brett right after this news break at the bottom of the hour. It's Valentine's Day night here in Boston and all around the world, It's.
Night Side with Ray on Boston's news radio.
My guess it's Carrie Brett, her new book, Shot at Love. And again you have to understand the double onendre here that covers beautiful Carrie Brett herself is a beautiful woman who comes from a tremendous family and has been through I guess the grinder is the way you describe it. It's described. The book is described as a fearless and funny memoir of heartbreak, resilience in finding love in the modern age. Your stepdaughter, your daughter, excuse me, your daughter
is now in college. So you were able to raise your daughter for most of it on your own while you maintained a very active business as a photographer, which was challenging. Uh and anyone out there who finds themselves in a situation and similar situation and needs to find someone who who can in effect throw them a life preserver, philosophical life preserver.
It would be you.
There had to been days, Carrie, when you went through this and again when I say you're beautiful, you're you're a beautiful woman, and you're also an awfully good and wonderful woman with a good heart and a good mind. There had to have been days when you had to see yourself that was wrong with me? That I find my self in this situation, And I'm sure it's in the book. How did you deal with those days when I guess you probably got up and said, you know, I don't want to get out of bed today.
I just want to go back to sleep.
But how did you continue to get yourself back in the game and back in the game successfully.
Well. The job that I had I loved, and so I was happy to go to work every day, to be honest, And I think that because I was so driven and worked so hard that always so I really didn't have a choice because I was a single mom and I had to keep the roof over my head and I had my little girl I had to take care of, so she really was my guiding light that if I couldn't fight for myself, I had to fight for her, and she really became my why because when
you become that hopeless, it's very difficult to carry on, and it's difficult to tell people that you're in that that low because if you come from a very proud Irish Catholic family like I do, that I think that was my hardest piece was that I was very good at concealing I thought anyways. I think I know people who are close to me could see it. But I was always at work early with a smile on my
face and never really complained. And I think that came as such a shock to everyone at the magazine that they couldn't believe that I did such a good job there and did all these things when what I was concealing about my past was was far from picture perfect. But I think that's a lot of you people.
How tough was it to finally say, Okay, I have to break out of my circle of friends, my my my loving family and and I know your family very well. Uh, and I'm going to get on these some of these new things that this dating app thing, which a lot of people probably would have said, I have no idea who I'm meeting and who they might be. We've all heard the horror stories of you know, people who have you know, bad experience.
Forget the experience where someone feels.
In danger, which is a horrific experience, but you show up and you know the person is not what they represented themselves to be on the dating app that had. That's jumping into the deep end of the pool and not knowing if you're going to be able to swim. That's the only metaphor that I can explain. How would you explain it?
Well, you said that with this showing up. When you said the word showing up. What made me think is that sometimes in life you need one person to believe in you, one person to show up. You don't need ten you need one. And in chapter fifteen, I had my longtime mentor who's a lot older than me. He's been a different type of teacher than my dad. He's a photography teacher, but he was a studio portrait artist where my dad is award winning photojournalist, so different types
of photography. And I get stuck on a shoot actually at spring training. He flies down to bail me out, and that's when he loses it, and he has this come to Jesus moment where he's like, Carrie, i've known you for twenty five that you're choosing the wrong people and the common denominator is you. And you're a smart girl who has a lot of gifts and a lot of abilities, and it's time that you use your head
and make some changes. And once he had to be once he was very clear, and I was pretty devastated to hear what he had to say to me. But sometimes you can't see the force in the trees, and at that point he could see. He said, for you, being alone doesn't work for you. It works for a lot of people. For you, it does not. And he said you need to shift the focus and shift the lens and start looking for a good person, not a good looking I mean, my boyfriend's good looking, but you
can be handsome but not very nice. And so I think I used my photography to look on the out exterior in the beginning of my journey, not meaning to, and it got me into a lot of trouble and I had to start looking.
Yeah, a tough message for that guy to deliver, and it had a tough message to receive.
It was you know what, well, I'm I'm very strong and I'm strong willed, and I and I have that fighting irish and me to to my detriment. I'll be honest, I think I get it from both of my parents. They're both equally strong in many ways, just differently, and so I have like the best of I have that for both of them. They're not quitters, they really aren't. And so I learned the hard way. But I really value my mentor, Jeff Lubin, and I was disappointing him
and I was disappointing myself. So that was the wake up all that I needed to make to do things differently and sometimes people sorry.
So what did you do differently? What did you do differently? What you pivoted at that point. You weren't being you know, you were not finding what you wanted.
Okay.
What did you do is that when you said okay, I got to jump on one of these crazy apps that I have no idea what it really is, but I'm going to give it a shot. Is that it No.
I was on the dating apps, but I was pulling in the same type of person, like literally to the t six to four looked like Tom Brady in a banker suit, like the same over and over type of person. Okay, And they were known they were unintentional daters, so they were passing time on these dating apps, and and so
I didn't know what an unintentional data was. I didn't know what any of these things were because this was the early game of all this, and so so I had to be open to something different, and that when I came home from spring training two days later, I was on a date with my boyfriend now and he too had to be very forgiving and open, and I think we both could see each other for the people that we were who had just gone through a lot
of hard things. And I really believe there's a lot of great people out there on these dating apps.
So when I get back. I want to find out. It sounds to me like you had this come to Jesus conversation with your mentor who was a professional mentor, but now he became a personal mentor, and within a period of a few days, you had kind of changed your focus very quickly, shot at love. So I want to find out, and I'm sure our audience who's listening
wants to find out what you did. So that'll be our question when I come back, if you're able to explain it, because it sounds like that a single moment, and it almost sounds like a confrontation where a friend said to you, Hey, you know you got to you got to change it up, and you change it up successfully within a fairly brief period of time. We'll get back with my guest, Carrie Brett, an award winning host top ranked dating podcast. She's been through the grinder, she
admits it, and this is an amazing book. I suspect many of you are going to want to buy it. And if you'd like to ask carry a question, I got wide open lines here. Oftentimes when I do interviews like this, Carrie, there are people who tell me.
Oh, it's a great interview.
I listened to it, but they don't want to call because they for me to ask the question that's on their mind. And I get news for your folks, then maybe questions on your mind that I haven't thought of.
We'll be right back on Nightside.
Now, back to Dan ray Line from the Window World night Side Studios on WBZ the News Radio.
When we went to break, Caerry, I was asking you about this moment when your professional mentor came to you and talked to you about your personal life. And matter of fact, one of the items that I'm reading here about the book says your mission is to inspire others who struggle to overcome the challenges of dating, just as she once did, to rediscover their confidence, reframe their stories, and take their shot at love. Obviously a lot of photographic metaphors in there.
What did you do in that?
I mean, it sounds to me like you came back from spring training and you hit the jackpot with a great guy who've been with now for eight years. How did you turn it around that quickly?
I'm a quick study like that. No, Honestly, there's people that I really value their criticism. And my friend Jeff, I know he's had a lot of personal struggles himself, and he had a son with bone cancer and so he was photographing health each children while his son was in the hospital for a long period of time, and so he knew real struggle. And yeah, it was really powerful, like he could see he saw a lot of himself
in me, different types of struggle. Like I mentioned earlier, But what I was doing essentially was I was judging a book by its cover, and I was messing out on wonderful people. And when I say judging a book by cover, the photograph that my boyfriend put up with a photograph of him and his brother, so I don't know who I'm swiping on again, early early years of Tinder.
And then he and then he had a line that said looking for love in all the wrong places, and I was like, that's I didn't know if that was funny or not. I thought, now, I kind of like it, but I judged that right. And then he went to the same college as my uncle Jim, and he went to American University, and I had a connection there with that because I knew that my dad's younger brother went there. So I thought, well, he must be smart because my uncle Jim's smart.
And a puzzle. You're kind, You're putting together pieces of a puzzle.
It seems to me right. So I didn't really like the looking for love. I didn't know who I was swiping on. But see now I'm opened. And the first thing he said to me was do you like the Bachelor? And are you watching the Bachelor? And I was like, no, I don't even what, Like, I just didn't watch those kind of shows. Now I watch them with him, and we love them. But like, see, you can easily judge people really quickly by certain things they say, certain things
they put in the profile. And now I was approaching dating with a different do you find her? And an open heart, fully optimistic and hopeful. And I even had a friend say, if you don't like him, you'll meet a girl. I think you will, but she said, I know him personally, and you'll end up with a great new single friend. And last I checked, Carrie, you don't have any single friends.
How did you have that? And I often say Boston, big city, small town, and I suspect that you might identify with that concept. How was it that you were able to connect a friend of yours who was also a friend of his. Is this all over the phone or is this after you have started at date a little while?
This is all texting, We're not even on the phone. This is the first that's my conversation.
I got to get into the twenty first century. Here go ahead.
Oh yeah, I mean, in truth, he really is very opposite of me. But I needed in the beginning of the book when I thank him, I say, if you're a kite, find a rock. So I'm someone who thinks really big and touch my goals to outrageous things, and he's the balance and counterpart, and so I needed to find someone opposite of me that was going to work for me. See what I'm saying.
No, I said, well, what do they I think?
Not to use cliches here, but they say opposites attract, and I happen to believe that too, to be honest with you, And you know, I'm not into like, you know, Asian meditation or something, but that you have some of these philosophers off of the Yang and the Yang and all of that sort of stuff. It's worked for you for eight years. What sort of occupation or business as
your boyfriend? Obviously you're in a in a very individualistic business where it's you with a camera and the subject, and your job is to capture the image of that individual, but also a sense of that individual if they're going to be in the cover of a magazine or something.
What does he do for a living?
So he's in real estate, and I think, yeah, yeah, it's perfect because he works for himself essentially, right, and he works for his clients like I do, and he works all the time.
It's also but it's also a very it's a much more tangible sort of it's a it's a tangible what's the house worth, what's the square footage? What are the real estate taxes? What are the crparables in the area. You're dealing in a totally different area. You're you're dealing in much more subjectivity. He's you're you're in chemistry, he's in physics mm hmm.
But he's also I think with with people who are making the biggest purchase of their life. There there is a lot of back and forth and you have to have a lot of patients if you want to be a good realtor, and he has a lot of patients with me.
Look, Carrie, I have loved this hour. I hope my audience has loved it. I know they'll love your book. Uh, it's available. I assume at this point, what's the easiest way for people to get the book?
Shot at Love and there, Ariazon, you can have a tomorrow. You can get it right away on Amazon. There's a couple of places downtown that is carrying it. I have it at my studio Thatcheran Spring Herman and the Green downtown Hingham. I'm going to be moving into other boutiques and if you want to sign up for my newsletter at shot at lovebook dot com. I'm going to be doing single events where you can come. You can come if you're in, if you're married, but just bring a
single friend. So I have done some shot at Love Live single events, and I'm going to be doing book signings through single events through the spring. Yeah.
Well, carry congratulations on the book, congratulations in the podcast, the congratulations and finding the love of your life, which is what Valentine's Day is really supposedly all about.
Thanks so much for tonight.
I enjoyed the conversation and I'm so happy for you.
I I don't know.
I'm happy for you on a professional basis, but also very happy for you.
On a personal.
Basis as a member of the Brett family, I feel sort of fair nice.
Thank you so much for having me.
I'll see you at the Food Pantry event in March in Dorchester.
Okay, okay, I'll be there
All right when we get back to twentieth hour, Ladies and gentlemen, twentieth hour of the week, and we're going to talk about what grinds your gears coming back on night Side