Brutally Anna

This week, I sit down with Brandon Berman and Harrison Forman, the creators of the viral live dating show, UpDating, where contestants date blindfolded in front of a live audience. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We discuss everything from whether they believe if men and women can really be just friends, the awkward beginnings of both of their LTRs and how they found success by not taking themselves too seriously. Brandon reveals why he gave his girlfriend an ultimatum two weeks into their relationship, while Harrison shows us all that sometimes, you haven’t found love because you’re not looking in the right place. We dive into where they believe all the good men have really gone (spoiler: some of them can be found at the UpDating after parties) and how they grew their live show from humble beginnings. For anyone who’s ever felt like they’ve been counted out, Brandon and Harrison want you to know that creating your own lane is always better than trying to compete in someone else’s. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Brandon & Harrison: @updatingshow @bermmy16 @htforman Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week, I'm breaking down my thoughts on Netflix's Ashley Madison documentary and the Laci Peterson story. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, date yourself, being behind, love and money, cheating, infidelity, narcissism, self-help Tune in for my thoughts on why (some) people cheat, why I think it's okay to be married to a cheater, but not to date a cheater, and how to spot signs of love bombing. We dive into the reasons why it's dangerous to commit to a relationship or a marriage before you've committed to what you want in life and how to spot the difference between someone who loves you and someone who loves what you do for them. I answer your voicemails on why a long-distance relationship turned cold once it was no longer long distance, and how to get your power back after getting your heart broken and watching your ex move on before you. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kaitlin Reagan knows a thing or two about letting go. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money In this week’s episode, I sit down with Kaitlin to talk about her journey as the daughter of a single mom in Brooklyn to TikTok stardom and losing her boyfriend, Francesco, to cancer along the way. Find out why Kaitlin doesn’t believe in long distance relationships, how she overcame her family history of drug addiction, and why she’s done trying to fit into anyone else’s life but her own. For anyone who has ever been angry at the cards they were dealt, Kaitlin’s story shows us all that it’s not about what happens to us, but what we do with what happens to us that determines our fate. We muse on whether it’s really possible to find everything you want in a man, why she still wears a promise ring from Francesco, and how she knew she was finally able to move on after his passing. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kaitlin @kaitlin_reagan Learn more about your ad choices. Visit podcastchoices.com/adchoices

Emotional baggage comes in many forms and mine comes when it's time to make our Christmas card. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I discuss the culture of Christmas cards and all the reasons why smiling photos of perfect families on a 5x7 make me feel some type of way and what to remember this holiday season if your life is looking a little less than picture perfect. I dish on what my "honest" Christmas card would say if I had carte blanche to write what I wanted on the back of our card and why sometimes, you're not behind, you're just on a different path. Tune in as I answer voicemails on whether you should choose love or money and just how important sex is in a relationship. Leave me a voicemail: speakpipe.com/brutallyannapodcast Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kelly Rizzo wants us all to know that it’s okay to laugh at death. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money She’s the creator of the award-winning production company, Eat Travel Rock Productions and recently competed on Fox’s Special Forces, but Kelly and I sit down today to talk more about how losing her husband, Bob Saget, forced her to learn that there is humor to be found, even in times of great loss. We tackle the topic of deciding not to have children, why it’s okay to choose the man over the life other people expect you to live, and how she’s managed to start over after having the rug pulled out from underneath her. For anyone who’s grappling with the loss of a spouse, Kelly wants us all to know that it’s possible to move forward and find love again without negating the love you once had. We discuss whether she would ever go on Special Forces again, her journey from atheism to Christianity and why she believes finding peace is more important than finding closure. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Kelly @kellyrizzo Learn more about your ad choices. Visit podcastchoices.com/adchoices

Happy Thanksgiving to all my American biddies and this Thanksgiving, I'm grateful for the psychic that made me realize that I needed to go back on Zoloft. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, I'm discussing all things antidepressants, medication, and why a bad reading from a psychic led me to get back onto a good path with my mental health. I answer your questions about how to disentangle your life from a long-term partner and how to get over your first love when it feels like you'll never be loved again and, how to handle Thanksgiving when you have nothing to be grateful for. Leave me a voice at speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

What’s it like to feel like an outsider your entire life? Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, we sit down with beauty and skincare influencer, Ava Lee, on life before going viral for her “jelloskin” tips and the power of reinventing yourself. Ava dishes on growing up in Shanghai and her first time in America as a college student at Notre Dame. We unpack the nuances of the Asian-American experience, assimilation, and how sometimes, we have to be who we are not in order to discover who we are. Ava and I detail our early days in social media and how we got over the cringe of being “that girl who thinks she’s an influencer”, how serving sizes are a uniquely American concept, and how she healed herself by going back to her eastern gastronomic roots. For all the biddies who believe in second chances, tune in to find out why it was not love at first sight for Ava and her husband Ben, and who her favorite ex was. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Ava @glowwithava @byava Learn more about your ad choices. Visit podcastchoices.com/adchoices

On this week's solo episode, I'm coming to you, kind of live, from my hotel room in LA with a mixture of gratitude and Wellbutrin. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money We're reminding ourselves that our mental state is not always an accurate reflection of what the reality is around us, and that having sad moments doesn't make us sad people, it just makes us people. For those of you who find yourselves in struggle city this time of year, tune in for my advice on how to light the fire under you to get yourself going when you're in a rut, and what to do when you're tired of dating, but not tired of hoping to find love. I answer your voicemails about how to stop being fetishized as an Asian-American woman on dates, and how to cope with your ex moving on and getting engaged to someone else. Leave me a voicemail: speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

Beauty influencer and TV host Cyrus Veyssi wants us all to know that if a space wasn’t made for you, you can make a space for yourself. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, Cyrus discusses their experience as a non-binary child of immigrants in suburban Boston, why it’s important to understand the difference between someone’s intent versus their impact, and how they use beauty as an act of forgiveness to themselves. We discuss queer dating, why Cyrus prefers to set up straight men and women, and their opinions for how couples should approach money in relationships. If you’ve ever felt limited by the social constructs of gender, sexuality, and identity, this episode is here to remind you that the only right identity is the one that frees you instead of limits you. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Cyrus @cyrusveyssi Learn more about your ad choices. Visit podcastchoices.com/adchoices

On this week's solo episode, I discuss why sometimes, losing everything you have is the key to getting everything you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money If you're wondering how to keep your life together when it appears to insist on falling apart, tune into this episode as we chat about how your "all is lost" moment is not your demise, but your redemption. I dive into the "all is lost" moment in my life that led me to my TikTok career, and why everyone should learn to dine alone. I answer your voicemails on how to determine what a man's intentions are on a date, when you should or shouldn't meet his parents, and how to move on from a man who fell out of love with you. Leave me a voicemail at https://www.speakpipe.com/brutallyannapodcast for me to answer on upcoming episodes. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

The queen of confidence, Serena F*cking Kerrigan, wants us all to know that you’re not delulu (*delusional in non-TikTok speak), you just haven’t been taught how to ask for what you want. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money This week, we discuss the importance of listening to your intuition, why Serena believes that we need to emphasize the importance of a woman being confident over a woman being palatable, and why she would never go back to an ex (spoiler: it’s like trying to un-spoil spoiled milk). Using her life as her muse, Serena reminds us all that no one knows what they’re doing, but that the ones who are successful are the ones who dare to try. My conversation with Serena sheds light on how the scarcity mentality implemented by the patriarchy forces women to settle and why you should never be confused in relationships. For anyone who has ever felt like they’ve taken the wrong turn in life, this week’s episode shows us all that sometimes, the wrong turn can lead you to the right destination in the end. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Serena @serenakerrigan Learn more about your ad choices. Visit podcastchoices.com/adchoices

On this bonus solo episode, we're diving into why dating apps are the gift wrapping of men and why I'm the not-so-proud owner of no less than a dozen cheese boards. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money Tune in as I unpack the psychology about why gift wrapping influences how much we like the gift itself, how it relates to dating, as well as why sometimes, the safe choice and the safe man isn't actually safe at all. I answer a listener's question about how to handle dealing with the fallout of choosing the wrong man when she was choosing between two men and why we should all look for the squatty potty of a man versus the cheeseboard of a man. You can now leave me voicemails to answer on future episodes here: https://www.speakpipe.com/brutallyannapodcast Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices

Vanderpump Rules star and entrepreneur Katie Maloney shows us why the path not taken is often the path we’re meant to take. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode Katie details her life as a college dropout, her days before reality TV and VPR, and how she decided that she could only find her best life if she found the courage to end her marriage. We discuss whether she would ever get married again, how she’s found peace as a single thirty-something in L.A., and how she’s no longer willing to be dragged into anyone’s drama, even if it means being alone. For anyone who has felt like their life has, metaphorically, ended, Katie’s story of overcoming a traumatic brain injury and her divorce shows us that there’s no limit, in her words, to the amount of software updates you can have in life.  Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Katie @musickillskate Learn more about your ad choices. Visit podcastchoices.com/adchoices

Lindsey Metselaar, host of the hit dating podcast, We Met At Acme, proves that getting dumped on your birthday can sometimes lead to great things. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this week’s episode, find out why women should listen to what men actually say, why Lindsey believes women are less likely to fall in love at first sight than men, and how the most heartbreaking relationships are sometimes the shortest ones. Lindsey talks about that time she was the other woman, quitting drinking (and other things), and who she thinks cheaters should marry. We unpack her PCOS diagnosis and her fertility journey and how Lindsey navigates her career and her newfound motherhood. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Lindsey @wemetacme Learn more about your ad choices. Visit podcastchoices.com/adchoices

We’re kicking things off with Violet Benson, host of the podcast Almost Adulting and the brain behind the viral Instagram account @daddyissues_. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money On this episode, we dive into how Violet managed to break the intergenerational trauma of her upbringing, why she thinks you keep attracting all the wrong men (aka Chads), and whether she really believes that you can meet the right person at the wrong time. Violet dives into her childhood as the daughter of Russian immigrants, the first boy that ever broke her heart, and the active practice of letting go of who you were so you can become who you’re meant to be. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Follow Violet @violetbenson @daddyissues_ @almostadulting Learn more about your ad choices. Visit podcastchoices.com/adchoices

Welcome to Brutally Anna, a podcast about finding love, losing love, and all the things we think about a lot, but don’t talk about enough. Keywords: dating, society, culture, relationships, love lessons, dating advice, toxic relationships, overcoming failure, single at the holidays, date yourself, being behind, love and money I’m your host, Anna Kai aka maybeboth across social media, here to remind you that life can be beautiful, even when it’s freaking brutal. On this brand new podcast, I’m joined by some of your favorite creators and experts on how they navigate dating, how to stay hopeful when you’ve kissed one-too-many frogs or Chads, and most importantly, how to love yourself when you haven’t yet found someone else to love you. Each week, we tackle everything from dating after divorce, how to ask for what you want from a relationship, and what death can teach us about love and life. If you’ve ever wondered how to begin again when life as you know it has ended, this podcast is here to remind you that the best thing to come out of rejection is often our reinvention. Join me for the premiere of Brutally Anna on October 28th with new episodes on Mondays as I sit down and get you the brutal truth so that you can find your truth. Don’t forget to follow me @maybeboth across social media and subscribe to Brutally Anna wherever you get your podcasts. Follow Anna:  https://www.instagram.com/maybeboth/ https://www.tiktok.com/@maybeboth https://www.youtube.com/@maybeboth Learn more about your ad choices. Visit podcastchoices.com/adchoices