PODCAST · comedy
Against My Better Judgment
by Dannelle Whiteside and Tamara Gauldin
Against My Better Judgment is where two friends—Dannelle Whiteside and Tamara Gauldin—get real about life and the lessons we learn the hard way. With a mix of humor, heart, and honesty, each episode dives into personal stories and the moments we knew better… but did it anyway.
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Episode 37: How We Do Partnership (featuring our first-ever special guest)
This episode of Against My Better Judgment blends collaboration with a sprinkle of “we’re really doing this together” delight. In “How We Do Partnership,” Dannelle and Tamara welcome the podcast’s first special guest to explore what it takes to build, maintain, and honor a true partnership — whether romantic, professional, or the beautifully complicated in-between. They dig into communication, compromise, and quiet agreements that make shared life possible. Expect heartfelt moments, unexpected laughter, and a fresh perspective on what it means to choose someone — and keep choosing them — on purpose.
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Episode 36: How We Do Sportsmanship
This episode of Against My Better Judgment blends competitive spirit with a sprinkle of “I’m trying to be a good person but also… I like to win” energy. In “How We Do Sportsmanship,” Tamara breaks down the art of playing fair, losing gracefully, and celebrating without being insufferable. She shares the lessons learned from childhood games, and the unspoken rules that govern everything from board games to workplace dynamics. Equal parts reflective and hilariously honest, this episode reminds us that character shows up even when the score is tied.
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Episode 35: How We Do Citizenship
This episode of Against My Better Judgment mixes civic responsibility with a dash of “why is adulthood like this” reality. In “How We Do Citizenship,” Dannelle unpacks what it means to show up for your community — from the everyday choices that quietly shape the world around us to the big moments that demand courage, clarity, and a little bit of common sense. She reflects on belonging, accountability, and the surprising ways citizenship shows. Expect thoughtful insight, gentle nudges, and a call for accountability.
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Episode 34: How we do Hardship
This episode of Against My Better Judgment blends resilience with a sprinkle of “life really tried it” humor. In “How We Do Hardship,” Tamara walks through the seasons that stretched her, sharpened her, and reminded her she’s built sturdier than she realized. She shares the coping tools, and quiet inner shifts that helped her navigate the moments that felt heavier than expected — and the surprising clarity that hardship leaves behind when the dust settles.
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Episode 33: How we do Mentorship
This episode of Against My Better Judgment blends generational wisdom with a dash of mentor‑mentee comedy. In “How We Do Mentorship,” Dannelle unpacks the teachers, elders, and unexpected guides who shaped her path — the lessons that stuck, the ones she had to unlearn, and the joy of pouring into others with intention. She reflects on mentorship as a reciprocal, evolving relationship rooted in honesty, curiosity, and care.
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Episode 32: How we do Ownership
This episode of Against My Better Judgment blends personal accountability with a sprinkle of “I really did that, didn’t I?” humility. In “How We Do Ownership,” Tamara reflects on the moments that forced her to step up — the choices she’s proud of, the ones she’d like to return to sender, and the growth that comes from claiming all of it without flinching. She explores responsibility as a practice, not a performance.
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Episode 31: How we do Allyship
This episode of Against My Better Judgment blends intentional growth with a sprinkle of social‑justice‑adjacent culture. In “How We Do Allyship,” Dannelle reflects on what it means to show up — consistently, humbly, and without making it a performance. She shares the missteps, mindset shifts, and meaningful moments that shaped her understanding of Allyship.
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Episode 30: How we do Leadership
This episode of Against My Better Judgment mixes courageous self‑reflection with the kind of workplace absurdity that makes you question who put certain people in charge. In “How We Do Leadership,” Tamara walks through the lessons, stumbles, and surprising strengths that shaped her approach to leading — the clarity, the compassion, and the quiet confidence that shows up even when she’d rather not.
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Episode 29: How we do Kinship
This episode of Against My Better Judgment blends inherited wisdom with the kind of family‑adjacent chaos that keeps group texts spicy. In “How We Do Kinship,” Dannelle unpacks the ties that hold us together — the chosen, the blood‑related, and the ones we claim only on holidays. She explores belonging, boundaries, and the tender work of staying connected even when life pulls in opposite directions.
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Episode 28: How we do Discipleship.
This episode of Against My Better Judgment blends spiritual growth with a sprinkle of church‑adjacent comedy. In “How We Do Discipleship,” Tamara reflects on the mentors, missteps, and meaningful moments that shaped her faith journey — the practices that ground her, the questions that stretch her, and the grace that keeps her steady when life is doing the absolute most.
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Episode 27: How We Do Scholarships.
This episode of Against My Better Judgment serves academic realness with a side of learned curiosity. In “How We Do Scholarship,” Dannelle walks us through her relationship with learning — the curiosity that fuels her, the discipline that saves her, and the academic politics. She unpacks her blueprint to try to stay relevant and informed.
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Episode 26: How We Do Friendships.
This episode of Against My Better Judgment explores the beautiful mess of adult friendships with a side of social‑circle drama. In “How We Do Friendships,” Tamara breaks down the art of choosing your people — the loyalty, the boundaries, and the subtle red flags you pretend you didn’t see. She shares the lessons, the losses, and the laughable moments that shape how we show up for each other.
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Episode 25: How I learned Boundaries
This episode of Against My Better Judgment traces Tamara’s journey into understanding boundaries—where they’re drawn, why they matter, and how they protect both compassion and clarity. Through personal stories that are equal parts funny and eye-opening, she shows how boundaries aren’t walls, but bridges to healthier relationships and self-respect.
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Episode 24: How I learned What’s in a name
This episode of Against My Better Judgment uncovers how Dannelle learned the power behind a name. From moments of misunderstanding to revelations of identity and belonging, she shares how names carry stories, shape connections, and remind us that who we are is often spoken before anything else.
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Episode 23: How I learned Compassion
This episode of Against My Better Judgment explores Tamara’s journey into compassion, shaped by her grandmother’s open kitchen and encounters with people who taught her what generosity really looks like. Through heartfelt, funny, and eye-opening stories, she shows how compassion isn’t just a virtue—it’s a practice that changes how you see the world.
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Episode 22: How I learned the Importance of a New Year’s resolution
This episode of Against My Better Judgment explores how Dannelle came to see New Year’s resolutions not as empty promises, but as powerful tools for reflection and growth. With candid stories and relatable humor, she reveals how setting intentions—even imperfect ones—can shape the year ahead in surprising ways.
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Episode 21: How I learned The Meaning of Christmas
This episode of Against My Better Judgment follows Dannelle’s discovery of Christmas beyond the glitter and gifts. What does Christmas really mean? For Danelle, the answer came not from gifts or glitter, but from a moment of clarity that changed her perspective forever. Join her as she recounts the journey that revealed the heart of the holiday.
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Episode 20: How I learned to Drive in the Rain
This episode of Against My Better Judgment takes you on a soggy road trip with Dannelle and her grandmother. Spoiler: Grandma’s calm warnings didn’t stand a chance against Dannelle’s lead foot (a family heirloom courtesy of her mother). Between hydroplaning lessons and hilarious hindsight, she shares how ignoring wisdom can make for the best stories—and the worst driving habits.
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Episode 19: How I learned Fight or Flight
This episode of Against My Better Judgment dives into Tamara’s real-life “fight or flight” moments—those times when the universe basically yelled, choose now! From awkward encounters to high-stakes decisions, she reveals how she discovered she’s not one to run but to stand her ground. Expect candid stories, a few laughs at her expense, and proof that sometimes fighting back means more than throwing punches—it means owning your choices.
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Episode 18: How I learned that God is real.
This episode of Against My Better Judgment finds Dannelle sharing the uncanny, sometimes hilarious, often tender moments that convinced her there’s more in life than coincidence. From improbable rescues to tiny everyday signs that felt like winks from the universe, she tells candid stories about faith, and the miracles that made her a believer. It’s moving, sometimes funny, and perfect for listeners who like their spiritual conversations honest, human, and a little bit uncanny.
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Episode 17: How I learned the importance of strategy.
This episode of Against My Better Judgment tracks Tamara’s early experiments with strategy that later built her career—think seeing now-moves for tomorrow’s invests and a plan or two coupled with actions that changed everything. She walks through youthful gambits that look charmingly audacious in hindsight, the frameworks she still swears by, and the funny missteps that taught her to plan and pivot. Tune in for clever, actionable takeaways and the kind of humblebrag that helps you level up.
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Episode 16: How I learned work-life integration.
This episode of Against My Better Judgment follows Dannelle as she confesses how she stopped chasing the mythical “perfect balance” and started building a life where work and home play nice. Expect stories about the time she turned a work event into a family night of football, and the small rituals that keep her present for both her family and home life. If you like practical tips served with wit and relatable chaos, this one’s for you.
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Episode 15: How I learned that being broke isn't for me
This episode of Against My Better Judgment serves hard-earned financial clarity with a side of office drama. In "How I learned..." Tamara explains how she learned that being broke is not for her — the mindset shifts, saving habits, and big risks that propelled real change. In "We'll be the Judge..." Tamara and Dannelle tackle a listener’s dilemma about a co-worker who is self-appointed as the PTO police, tattling on time off and policing boundaries. Expect money lessons and mic‑drop rulings. Laughs guaranteed, moral superiority optional.
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Episode 14: How I learned to live without a loved one.
This episode of Against My Better Judgment blends the quietly brave with the absurdly petty. In "How I learned..." Dannelle shares how she learned to live without her father as a young adult — she guides us through grief, growth, and the small, stubborn ways life moves forward after loss. In "We'll be the Judge..." Tamara and Dannelle prosecute a hilariously petty case: your friend the Wi‑Fi thief. Equal parts tender and unforgivingly funny. Expect empathetic truth and a verdict that’s equal parts common sense and comic relief. Bring tissues and snacks.
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Episode 13: How I Learned to Fit In
Co-hosts Dannelle Whiteside and Tamara Gauldin launch Season 2 with two fresh segments; "How I learned..." with Tamara’s story about fitting in: the missteps, the compromises, the unexpected friends, and the single moment she realized she didn’t have to change. Then in "We'll be the Judge..." they rule on a listener’s Halloween etiquette query — costume boundaries, candy politics, and whether to knock on the door when lights are off! Witty, warm, and sharply practical — justice served with a grin.
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Episode 12: That time when I learned fat was not a feeling
In this powerful and deeply personal episode of "Against My Better Judgment," Tamara recounts her struggle with the pervasive feeling of "being fat" and how it led to battling an eating disorder. Through her honest and courageous storytelling, Tamara shares the emotional and psychological challenges she faced, the journey towards self-acceptance, and the important realization that fat is not a feeling. Tune in to hear her story and gain valuable insights into body image, mental health, and the path to healing.
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Episode 11: That time when my Grandma left me instructions.
In this touching and reflective episode of "Against My Better Judgment," Dannelle shares the moment she discovered she was the executor of her grandmother's estate. Through her heartfelt narrative, Dannelle recounts the emotions and responsibilities that came with this revelation, as well as the valuable lessons she learned along the way. Tune in to hear her story and gain insights into the importance of end-of-life planning and the unexpected ways our loved ones continue to guide us even after they're gone.
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Episode 10: That time when the kids came over
In this insightful and entertaining episode of "Against My Better Judgment," Tamara shares her experiences and tips on hosting kids in a childless home. From preparing for the adventure to understanding the correct etiquette, Tamara offers practical advice and humorous anecdotes that will help you navigate the challenges and joys of having young guests. Tune in to hear her stories and learn how to create a welcoming environment for kids while maintaining your sanity.
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Episode 9: That time when I had a Surprise Baby!
In this episode of Against My Better Judgment, Dannelle gets real about the plot twist that even she didn’t see coming—a surprise third pregnancy when life felt full enough with two boys already. She unpacks the mix of disbelief and excitement. If you've ever found yourself saying, “Well, that wasn’t on the calendar,” this one’s for you.
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Episode 8: That time when I joined FB at 45 years old.
In this amusing and insightful episode of "Against My Better Judgment," Tamara shares her experience of diving into the world of social media after 45 years of resisting the hype. From joining Facebook to exploring four other platforms, Tamara offers a unique perspective on the challenges and surprises of navigating the digital landscape. Tune in to hear her stories, the lessons she learned, and her tips for anyone considering taking the plunge into social media.
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Episode 7: That time when I had an anxiety attack
In this candid and relatable episode of "Against My Better Judgment," Dannelle opens up about her experience with an anxiety attack and how she discovered that coffee and life don't mix. Through her honest and heartfelt storytelling, Dannelle shares the moments leading up to the attack, the symptoms she experienced, and the steps she took to manage her anxiety. Tune in to hear her story and gain valuable insights into recognizing and coping with anxiety in everyday life.
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Episode 6: That Time When I Almost Got Scammed
In this gripping and eye-opening episode of "Against My Better Judgment," Dannelle shares her harrowing experience of narrowly avoiding a scam that involved cash withdrawals and the sheriff's department. Through her detailed account, Dannelle reveals the red flags she noticed and the steps she took to protect herself. Tune in to hear her story and learn valuable tips on how to recognize and avoid scams, ensuring you stay safe in today's increasingly deceptive world.
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Episode 5: That time when I discovered a stranger living in my house
In this astonishing and intriguing episode of "Against My Better Judgment," Tamara recounts the unbelievable story of how a friend's mistaken identity led to her unknowingly accepting a stranger into her home for months. Through her captivating narrative, Tamara shares the bizarre events that unfolded and the lessons she learned from this extraordinary experience. Tune in to hear her story and discover how a simple mistake can lead to unexpected and unforgettable adventures.
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Episode 4: That time when I realized my brother is my mom’s favorite
In this heartfelt and humorous episode of "Against My Better Judgment," Dannelle takes us on a journey through various scenarios to when she realized her brother is her mom's favorite child. From childhood memories to recent events, Dannelle shares her experiences and insights, offering a mix of laughter and introspection. Tune in to hear her candid stories and discover how family dynamics can shape our perceptions and relationships.
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Episode 3: That Time When We Went on a Mission Trip
In this episode, Dannelle and Tamara swap stories about the very different mission trips they each took—moments that stretched their faith, tested their patience, and left them forever changed. From awkward cultural missteps to powerful spiritual lessons, they explore how serving in unfamiliar places shaped their views on purpose and compassion.
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Episode 2: That time when I made a crazy choice to upend My life.
In this episode of "Against My Better Judgment," Tamara gets real about a pivotal moment when she made a choice draft a resignation letter—leaving behind security and predictability for a future that was anything but certain. Dannelle and Tamara unpack what it takes to follow a nudge that doesn’t make sense on paper, the fear that comes with risking it all, and the surprising ways faith and friendship show up when you are bold enough to bet on yourself.
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Episode 1: That Time When We Started a Podcast
Welcome to the very first episode of Against My Better Judgment! In this kickoff, two longtime friends—Dannelle and Tamara—decide to hit record on the conversations they’ve been having for years. They share why they started this podcast, what you can expect each week, and the stories that pushed them to finally take the leap (even if it was, well... against their better judgment). This episode’s signature segment has Dannelle recounting an unexpectedly chatty Uber ride and Tamara opening up about an awkward first visit to a new church—because sometimes the moments that humble us the most are also the ones that teach us the most. Get ready for honest reflections, hearty laughs, and the start of a season all about those “can you believe this happened?” moments.
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ABOUT THIS SHOW
Against My Better Judgment is where two friends—Dannelle Whiteside and Tamara Gauldin—get real about life and the lessons we learn the hard way. With a mix of humor, heart, and honesty, each episode dives into personal stories and the moments we knew better… but did it anyway.
HOSTED BY
Dannelle Whiteside and Tamara Gauldin
CATEGORIES
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