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Modern Dating, Self-Worth, and Confidence with Dating Expert Kerry Brett

26 min
Apr 15, 2026about 2 months ago
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Summary

Dating expert Kerry Brett discusses modern dating trends, self-worth, and confidence in relationships. The episode covers how digital dating has transformed romance, the importance of authentic self-presentation, and practical advice for navigating contemporary dating apps and relationships.

Insights
  • Online dating should be treated as marketing and branding—profile photos and presentation directly impact dating success and connection quality
  • Authenticity and vulnerability create genuine connections; showing up as your true self rather than a 'representative' increases chances of finding compatible partners
  • Self-worth and personal fulfillment must precede romantic relationships; relying on partners for happiness undermines relationship dynamics and longevity
  • Ghosting and rejection often reflect the other person's limitations, not your value; reframing these experiences prevents emotional damage and maintains confidence
  • Mindset and belief in one's worthiness of love are foundational; without hope and self-belief, dating efforts become ineffective regardless of effort
Trends
Digital dating has become mainstream and normalized; online meeting now rivals traditional in-person introductions for relationship formationProfile optimization and visual branding are critical success factors in dating apps; photography quality and strategic bio presentation directly correlate with matchesAuthenticity and vulnerability are increasingly valued in dating; users seeking genuine connections prefer partners who present their true selves earlyGenerational shift in dating norms; single parents dating, cohabitation, and non-traditional relationship structures are now socially acceptable and commonPsychological frameworks like law of attraction and karma-based thinking influence dating confidence and relationship expectations among modern datersDating app fatigue and 'perpetual daters' are emerging phenomena; some users remain on platforms long-term without commitment intent, wasting others' timeGender dynamics in dating are evolving; traditional courtship expectations (men paying, initiating) persist but are increasingly questioned and negotiatedGhosting and communication avoidance have become normalized dating behaviors; managing rejection and non-closure is now a required dating skill
Topics
Online dating apps and digital courtshipProfile optimization and personal branding in datingDating red flags and green flagsSelf-worth and confidence in relationshipsGhosting and rejection managementAuthenticity vs. representative self-presentationFirst date etiquette and expectationsLong-term relationship maintenanceDating as a learnable skillMindset and law of attraction in datingGender roles and courtship expectationsCelebrity relationship analysisHealing from heartbreak and past relationshipsCommunication and honesty in datingDating app strategy and opening lines
Companies
Tinder
Kerry Brett joined Tinder in 2014 as an early adopter and built her dating expertise through the platform
Bumble
Mentioned as one of several modern dating apps available to users alongside Tinder and others
Match.com
Referenced as an early online dating platform where the host's friend met her husband
People
Kerry Brett
Guest expert discussing modern dating trends, self-worth, and relationship advice based on 10 years of dating app exp...
Julie
Host conducting interview and rapid-fire dating questions with Kerry Brett
Howie Mandel
Featured in multiple sponsor segments discussing OCD and mental health treatment
Nicole Kidman
Used as celebrity example of relationship challenges and the importance of honesty in partnerships
Michael Oze
Referenced for law of attraction principles that influenced Kerry's dating mindset and belief system
Quotes
"Stop trying to be somebody that you're not because you've got to see if they love you for you"
Kerry BrettMid-episode
"You can't rely on someone else to make you happy. You have to make yourself happy"
JulieMid-episode
"The energy that you bring into it is really really important and your mindset is everything"
Kerry BrettLate episode
"When you get ghosted you have to not take it so seriously. The majority of the time the reason why they ghosted you is because they either can't rise up to meet you or they're really not worthy of you"
Kerry BrettMid-episode
"Heartbreak is the price we pay for just daring to love, daring to be bold, daring to put our trust in someone else"
JulieLate episode
Full Transcript
There's the part of me that everyone sees. I'm Howie Mandel the comedian. Apparently I know what funny is. Funny bought me a house But I also know what isn't funny. OCD. I've lived with OCD my entire life and people throw the term around like it's no big deal But OCD is severe often debilitating. It's a mental health condition that involves Unrelentied unwanted thoughts that can make you question your character your beliefs even your safety General therapy can help with some things but for OCD it can actually make things worse That's why I want to tell you about no CD No CD is the world's largest treatment provider for OCD and is covered by insurance for over 155 million Americans their licensed therapists specialized in ERP the most effective treatment for OCD if you think you might be struggling with OCD go to No CD comm to book a free 15 minute call. They are here to help The Jack Welch management Institute at Strayer University helps you go from I know the way to I've arrived with our top 10 ranked online MBA Gain skills you can learn today and apply tomorrow Get ready to go from make it happen to made it happen and keep striving Visit Strayer edu slash Jack Welch MBA to learn more Strayer University is certified to operate in Virginia by Shev and as many campuses including at 21 21 15th Street North in Arlington, Virginia Welcome to obsessed where comfort zones go to die and transformation is non-negotiable Each episode will challenge what you believe disrupt the patterns holding you back and Dare you to live a life so bold? It scares you obsession is not a weakness It's the fire that forges greatness if you're ready to stop existing and start living then buckle up It's time to get obsessed Dating has changed so much in the past few decades since I was a kid back in the 90s Dating and trying to figure it out today. We have dating expert Carrie Brett author of shot at love and Podcast host if she knows everything about dating you're gonna need to know what is going on in the dating world because it has turned Digital it has changed it is morphed and it can be tricky These days Carrie you are our dating guru Tell us a little bit of your background and maybe why I'm calling you a dating guru. Hi Julie Thanks for having me on the show today. I am a professional photographer by trade. I became an early evolution dating app user in 2014 I've been in the dating space for 10 years and I joined Tinder because my career was in the business of dating Joined Tinder because my photography assistant who was 25 at the time put me on Tinder and my whole world changed and I had all this opportunity and I stopped crying and little by little I built my confidence back by dating on Tinder Now that's so funny because the word Tinder did not exist back in my dating days And I was not a very good dator by the way. I would say I was a serial Monogamous I would meet somebody and I would date them for three or four years Break up with them and then find somebody else dating apps Tinder bumble, I don't I don't even know all the words match.com Christian mingle coffee and a bagel Farmers only those things did not exist actually. I probably Ashoed those names match.com came out in the later years and my best friend from grade school She met her husband on match.com at the very beginning I was kind of like in the back of my head a little judgy I was like, oh, why do you have to go to the computer to meet a guy? Right well people who are married and people who are in relationships are the first to judge they're the first to judge something that they don't know anything about and I Didn't let that stop me. I didn't let other people's opinion hurt my chances of finding love Love hasn't always been an easy road for you as well and we often teach people what we have struggled with So can you give us an overview? We know your expertise because we are gonna dive deep into your expertise that will excite all of you guys That will give you hope whether you are dating whether you are exiting a relationship Whether you're a parent and you're trying to figure out what the heck your kids are doing Why are you an expert in dating Carrie? Well, I became obsessed with it when Realized I didn't have much competition because I was 43 when I joined and I had a 13 year old and people really believed that Online dating especially Tinder was a hookup site I believe at the time a lot of men were there because it was like a video game to them But not a lot of women in Suburbia outside of Boston were running to join Tinder So a lot of people made fun of me Because they didn't know what it was because it was relatively new. What year was this Carrie? 2014 so it was new and maybe a little weird. Maybe I was judging you yeah, it was a disaster out there dating and there's no information and terms like gas lighting and ghosting and Thrupple and all these crazy terms that are mainstream now. I had zero information So the reason why I wrote my book was for the girl I was back in 2014 and it's been a long road It has been a long it's been 20 years in the making so I start when I get divorced with a baby in chapter one and How my girlfriend and I we use bracelets Conversational bracelets to talk to men. We didn't have cell phones and I was dating with a baby on my hip and nothing more sexy than that by the way Get to for the price of one That's funny that speaks to how it changed because nobody did that back in the 50s 60s or 70s or they did it underground now It's just commonplace to be dating with your kids and bringing tons of baggage along with you And is dating today actually safe, you know the digital dating I would guess there's a lot of cat fishing or you know, you see those profile pictures It's like and no offense to the realtors in our lives. Oh, sorry Scott actually carries Significant other is a realtor But you see those big billboards of realtors and their pictures from 15 years ago and then you meet them in person and you're like Oh, you don't even know they're the same person because there's that bait and switch Do you see that a lot with modern dating guys back then and I still think it's true They put very little effort into their photographs Which is a huge mistake because your leading image and that's why I started to get really obsessed with it Is because I could see that online dating was marketing and branding 101 and there was no difference between my leading photograph or a cover that I would shoot for the improper Bustoni in the magazine that I worked for for 28 years and That it's very strong and it opens up doors for you It's how you position yourself your marketing yourself if you don't take that piece seriously It's not gonna be you're not gonna have great results So a lot of guys most guys will hold up the fish or their golfing or there they make a lot of mistakes with their photographs That's gotta be funny. You probably have some funny stories Oh, I've seen I I have 800 plus color-coded Photographs from Tinder that I started piecing this all together What the good-looking guys do and I started to do what those guys did and it worked so Typically the hot guy the guy that knows they're really good-looking Would never put anything in the bio because they didn't need to because they were so good-looking and they knew how good-looking they were and I realized that a lot of women were putting all these things like I love cooking and I love the red socks and a Lot of the things that they were saying was a lie So I decided to beat them at their own game by not putting anything in the profile and that freaked guys out big time because they were like This girl's doing the opposite of everyone else. It's it was like I took it away from them So they had no information about me. So then They were scrambling but they had to work harder to get to know me Because there was no information in the bio and I think if I ever had to go back on online dating today I think I would still do that because it worked so well for me But now we have Google and speaking of Google now before dates You can actually Google whoever you're going out with that is a smart move just finding out the backstory Who is this person this lady or dude? I'm going out with right and yeah who they are. Well, we did not have that. No, but I am blind by the seat of our pants totally, but as you know how people position themselves online Especially through social media. It's not always the truth and since I'm the queen of optics and that's my specialty That's how I make my living is making people look better than they do in real life. I believe why not put your best foot forward and Get some good photographs. It is marketing I've never really thought of dating as marketing, but we always when we start dating we are on our best behaviors When do we start shedding those layers and just becoming ourselves and freaking the other person out and seeing can they handle? Can they handle the truth? Can they actually handle all that we are because that is the scary part? Whether it's us or a partner, but there is that sunny moon period where Everybody loves us. We're awesome. Well, here's the thing most people show up as their representative not as themselves and They rob themselves of the opportunity of having a true connection So by the time I met my boyfriend We did not show up as our representatives We showed up as ourselves and the reason why we did that is because we were both so bloodied and Bruised and beaten up by the time we met that we didn't have anything left in the tank to try to be Someone that we weren't so that's when I really learned that Stop trying to be somebody that you're not because you've got to see if they love you for you Hmm and God didn't give me a filter unfortunately So I don't really know how to pretend to be somebody else It would be exhausting. I'm not a good liar and I don't have a poker face, right? And it's fun and it's challenging and it's gritty and it's Exciting when you do meet somebody else, but I love that you and your boyfriend, which I would honestly you guys have been together I I would consider you Kamala husband and wife, but I don't want to push you in any direction But being together for so long and just knowing each other off the bat that is courageous Have you seen any differentiation in your personality or his personality in the past? Decades since you've been together These things right? You have seasons and it's a lot of work and it's two people showing up to commit to that relationship We both wanted that we both really wanted to find love and He was all in from the beginning which I wanted really badly and I didn't have that in my past Relationships, so I really got to a place finally that I had Some worth because it didn't start that way That's a huge thing becoming or being whole before you even step into a relationship Because you can morph into the other person if you don't have a sense of self Mm-hmm, and if you don't have a sense of self you can bloat who you are and change the whole Dynamics of the relationship. I love that you said that well You can't rely on someone else to make you happy You have to make yourself happy and I think that's a big mistake that people make is there like when I find love I'll be happy Yeah, it enhances your life you should find you should look for someone that makes your life better That doesn't take away from you That's what's going right one of the things before we got married. I believe my husband asked my dad He said what is the key to a long-lasting marriage a relationship and my dad said get a hobby and My husband was like, huh? That's so weird But you know have who you are as A couple but know who you are as a person and do something you love on the sidelines is really what he meant and I Think about that as knowing who you are you have to know who you are and what you love Right something else besides your relationship with your partner So right my dad is not a dating expert like you are Carrie Brett shot at love expert And you know why we have Carrie Brett here We have Carrie Brett here because she is going to give you every single piece of dating advice She has in her vault of knowledge of dating She has dated probably every single type of person you could imagine and she knows everything about dating her stories are crazy Every time we have a conversation she pulls from that brain of hers And she's like oh this person this person this person this experience this experience You are going to sit privy right now as we do a rapid fire on all things dating and expertise In dating Carrie get your pencils out so you can Understand what dating is like now for you or in the future if you're thinking about dating or maybe you know someone That's dating you can give them some advice or share this episode with them Carrie are you open to a rapid fire just so we can pick your brain and learn everything about dating today? You're okay with that love it Hi Obsessors I'm obsessed with cozy earth as you know I have four boys and it is beautifully catech and it's loud It's busy and it's non-stop and that's why I am obsessed with cozy earth at the end of my day It is an exhale. It's the softness. 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Oh, no We help people customize and save on car insurance with Liberty Mutual together. We're married Need a human him to a bird. Yeah, the bird looks out of your league anyways Only pay for what you need at Liberty Mutual comm liberty liberty liberty There's the part of me that everyone sees I'm howie Mandel the comedian apparently I know what funny is Funny bought me a house, but I also know what isn't funny OCD I've lived with OCD my entire life and people throw the term around like it's no big deal But OCD is severe often debilitating. It's a mental health condition that involves Unrelentied unwanted thoughts that can make you question your character your beliefs even your safety General therapy can help with some things but for OCD it can actually make things worse That's why I want to tell you about no CD No CD is the world's largest treatment provider for OCD and is covered by insurance for over 155 million Americans their licensed therapists Specialized in ERP the most effective treatment for OCD if you think you might be struggling with OCD go to No CD comm to book a free 15 minute call. They are here to help You've never been one to settle stand down or stand still you're a lifelong learner Energized by excellence. There's a fire inside you. You can't ignore you've got competition to outrun Momentum to build on and your own high standards to meet stop now Not a chance at Capella University We help you catch what you're chasing because you've always had the drive now go earn the degree Capella University what can't you do visit? Capella edu to learn more. Are you nervous? No never done this before Okay, let's do a rapid fire and learn everything about dating right now by Kerry Brett Let's go biggest dating red flag being rude to a waiter or a valet or a doorman because if they're gonna jump ugly quickly in public like that and urine for a long Painful journey with that person one green flag everyone should look for I think people should look for their heart and what's inside matters because Good-looking doesn't mean a goddamn thing if they're not a good person so true Can you give us one example celebrity example? Well, I would a celebrity example Sure, Nicole Kidman right now. That's a hot story Mm-hmm, and I always say that things that you overlook in the beginning will be the thing that breaks you in the end and Sure enough a few months into their marriage he had to go away to take care of his addictions and he wasn't very honest about that and from all I know about that relationship is that The only thing that Nicole Kidman has said is that he hasn't been honest So that says enough People's pain isn't gossip people. I feel sorry for her right now and I'm sure it's very painful They were together for a long time, but relationships sometimes don't stand the test of time Yeah, I mean 19 years for a celebrity marriage that seems Almost like a lifetime in real life, right? I feel sad for the kids their daughters I think she's gonna have a great comeback. I can I can see that she seems very strong and she seems very caring and I'm rooting for her so that's still a word team Nicole here. I'm guessing here team Nicole I think she's really talented and I think that life with a Musician is very challenging. Ask Gwen Stefani, Gwen is Paltrow, Christy Brinkley The list Kate Hudson which goes on and on see very knows everything about dating that is for sure love and marriage I love this. Okay next question for Carrie Brett first date deal breaker If he doesn't pay for the date, that's a pretty strong sign because I don't want to be splitting bills over buffalo chicken nachos This is that old-fashioned is that old-fashioned Carrie? I think that the man should court you and Hunt you down and Make efforts and make plans pay for you make you feel important if they're not gonna do that in the beginning When are they gonna do it? Yeah? Yeah, no, I agree. Okay. That's the stage for what's to come stage, right? Hmm. I love that better to meet online or in real life I think whatever resonates with you is your answer If you like online dating Try out a bunch of different dating apps see what happens if you're quiet and you don't like to go out by yourself to a bar or a Networking event that might not work for you Either and online dating might be easier for you I mean putting yourself out there is hard no matter what avenue you pick Do you have to not take it all so seriously? or your You'll have a harder time and I would suggest having some patience With the process and with yourself and having a lot of grace because you're gonna make mistakes because you're learning Something new dating is a skill that can be learned just like anything else Did not know that dating is a skill that can be learned if I only knew this 30 years ago What's the best opening line on a dating app Well, I like when people do the shock and awe where they take a chance and they take a risk And they are really bold and really unique like I had one guy say to me smart sexy single or something like that I can't remember what it was, but it got my attention and He asked me out he didn't even talk to me He just asked me out right away and that got my attention and I said how did how do you know that? You want to go out with me and he's like see the first text smart sexy single and so stuff like that. I really like those eye grabbers and I Learned that because again, I don't have a filter and I used my humor to survive That was one of my tools in my tinder toolkit was my humor and the fact that I was very raw and real You know me Julie that's I am like that in person so It worked for me because I always said the damnedest things and that Humor piece made people leaned in and that's when I said in the beginning of the episode When you show up as your representative you're losing your chance for true connection Yes, no, that's that's really good and you do say the damnedest things so we're gonna ask you next Best way to handle ghosting Sometimes a relationship falls apart and it has nothing to do with you and when you get ghosted you have to This is when I say don't take it also seriously I would say the majority of the time the reason why they ghosted you is Because they either can't rise up to meet you They're really not worthy of you or they have unhealed issues That you have pointed out probably unknowingly That makes them feel uncomfortable or the other one is there's an awful lot of unintentional daters on these dating apps love a pen pal love an ego stroke love money in a tip jar and Love someone to pass the time with but they're really not Interested in doing the work to be in a committed relationship So they did you a favor because they can't do it anyways and half the guys I dated Ten years ago are still on these dating sites and they will remain there Wow. Yeah, it blows my mind That's kind of a sad existence. I would think No, it works for them. Okay, otherwise they wouldn't be there Okay, it's sad for someone who wants to be in a relationship Because they just wasted your time but that's what I'm saying you have to reframe the ghosting and Find some friends to go out with there are people that can remind you of your worth because what's Gonna happen is gonna happen and who you're supposed to end up being with will unfold What is meant to be is meant to be is what I'm trying to say, right? So, how do you know when they're the one well? I think when you find someone that you are willing to take a shot with You have to you know, hope for the best because people change over time nothing is Ever guaranteed and that's where it can be hard and it can be complicated and it can be messy but You have to take a chance Somewhere you have to take a chance to trust somebody again And I think you know and I think you're inter-knowing your compass your Intuition knows You always know down deep You do and we don't necessarily listen to our intuition because we want something so bad that We're willing to sacrifice the truth and our hearts Because we want it so bad. Oh, yeah, we've Crazy crazy things. Yeah, you have like clean people's toilets and Done so many insane things I was like a maid I was a janitor I assumed lots of roles to Twist myself into a pretzel to be something I was not to please someone else with the hopes that I would someday be picking a maid of honor rather than being their maid Wow, wow That's powerful carry powerful. I mean if you can't learn from your past lessons What can you learn from this is really incredible? And if we wrap this up in a bow tie this all up in a package under the tree What is the best advice you've ever received about dating and relationships? Or have given somebody that can change the trajectory of their life like just what is it? Because dating is so hard the energy that you bring into it is really really important and Your mindset is that everything now I've watched my mother battle cancer for six well five five years well since December of 2019 and And She's not having it like she doesn't give any weight to cancer her mindset is so powerful and I think you have to come in with a winners mindset You are gonna rock it on these dating apps or wherever and you have to believe 100% that you're worthy of love and that you can find it and that was the best thing that I did And I didn't just have that but like that belief because often when you come out of a heartbreak You have no hope at all and when you have no hope all is truly lost And I've been there many times in my life so if you have that belief and the only reason why I had that belief is because My psychic healer told me karmically I was due and that all the love that I put in my past relationships would come back to me tenfold and because I believed in karma I Had that belief and that was a gift that she gave me and I write in my book that if you Have doubt look for proof and Michael Oze taught us that the law of attraction Have you found love before well if you have chances are you'll do it again Love is finding love and love is our birthright. It's ever present within us and If you just put yourself out there you will find love. Thank you so much. I wish I knew this back when so I could sidestep all the mistakes I made but mistakes are what mold us Heartbreak is the price we pay for just daring to love to daring to be bold daring to put our trust in someone else It cracks is open it reshapes us and allows us to be vulnerable to somebody else It allows us to be courageous in front of someone else and it teaches those lessons So you are constantly teaching us lessons of connection of understanding our self-worth and I'm telling you guys you need to read shot at love you need to listen to the podcast shot at love You are gonna dive deep into understanding What love can look like at any age at any stage? It's funny. It's witty the experts are there Carrie Brett She is changing the face of love for everybody check out shot at love get obsessed with Carrie Brett. I really do hope people pick up the book because there isn't anything I haven't lived through There's so many different stories and there's so many lessons for all ages I have a lot of divorced dads loving my book. It's for men and women and I can help people in all age groups. We all need to learn these skills and it does start worth worthiness and you've got to find a way to Believe that you're worth more. Yeah, you are worthy. You are worthy of scissors follow Carrie Brett Everything's in the show notes until we meet again wait review subscribe and love ourselves Our dating guru Carrie Brett. Love you. Thank you. Thanks so much With verbals last-minute deals you can save over fifty dollars on your spring getaway So whether it's a mountain escape with friends a family week at the beach or sightseeing in a new city There's still time to get great discounts book your next day now average saving $72 select homes only There's a part of me that everyone sees I'm how he Mandel the comedian apparently I know what funny is funny bought me a house But I also know what isn't funny OCD I've lived with OCD my entire life and people throw the term around like it's no big deal But OCD is severe often debilitating. It's a mental health condition that involves unrelented Unwanted thoughts that can make you question your character your beliefs even your safety General therapy can help with some things but for OCD it can actually make things worse That's why I want to tell you about no CD No CD is the world's largest treatment provider for OCD and is covered by insurance for over 155 million Americans their license therapists specialize in ERP the most effective treatment for OCD if you think you might be struggling with OCD go to No CD comm to book a free 15 minute call. They are here to help There's a fire inside you you can't ignore stand still not a chance You're a lifelong learner who's come this far now. We're here to help you keep going further Capella University What can't you do visit Capella dot edu to learn more? Let's talk groceries Specifically your groceries with Instacart you want your groceries just the way you like them, right? Well the Instacart app lets you do just that they have a new preference picker that lets you pick how ripe or unripe You want your bananas shoppers can see your preferences up front helping guide their choices Instacart get groceries just how you like If you liked the show, please take a moment to rate review and subscribe It really does help the show to grow. Thank you for listening