Sunday Questions the Podcast

In this episode of the Sunday Questions, Cailin shares her personal insights on relationships: what helps them grow, where things can get tricky, and how we learn about ourselves through them.She talks through 10 key lessons from her two-year relationship with Sam, touching on communication, admiration, and the quiet ways we shape dynamics over time. From emotional loans to setting healthy precedents, this episode explores the small patterns that make a big difference.

This week on Sunday Questions, Cailin is joined by friend, songwriter, and former division one lacrosse player Lilly Drury for a conversation on purpose, presence, and the quiet power of hard work. Conversations span from the role of writing as a lifelong practice and the importance of self-talk, to how we can reconcile suffering every day. Lilly shares why vulnerability builds connection, how hobbies can ground us, and what it really means to build a meaningful life.

In this episode, Cailin sits down with Clinical Psychologist and author Bradley Frank, PhD, for a heartfelt and insightful Q&A on all things mental health and life guidance. From navigating grief and mending strained family relationships to embracing your authentic self in your 20s, we cover it all. Brad shares actionable advice and compassionate wisdom to help you heal, grow, and live unapologetically. Whether you're seeking guidance or simply curious about the journey to emotional well-being, this conversation is one you won't want to miss.

In today's episode, Sam joins Cailin for part two of their previous episode - but today, they're answering questions from listeners on things ranging from rejection, to maintaining your independence in a relationship, to the impact of OCD on a relationship. Enjoy, and happy Sunday!

In today's episode, Cailin is joined by her boyfriend, Sam, to discuss the phase of life and their relationship that they're in right now. They break down the most difficult conversations they've had throughout their relationship, and Sam shares the habits that he's built to support himself during a season of uncertainty. Disclaimer that the word "universe" might actually be used over 100 times in this episode. We love you!

In today's episode, Cailin discusses 10 lessons she's learned in corporate America. Topics include: leaving a role gracefully, how to get an interview, navigating difficult situations and uncomfortable conversations with coworkers, and how to advocate for yourself in the workplace.

Today's episode includes life updates on Cailin's career and an exciting new pivot, next steps in moving & what she's been up to lately. Getting into a Q&A, we break down the mindset shifts, wellness habits, and personal growth strategies that actually help, instead of overwhelm in the new year. This episode is full of advice for people in their twenties and anyone who is interested in self-development with topics including new years resolutions, supporting a struggling sibling, and best advice for second-semester seniors in college. Thank you for being here, I love you!

What a treasure it is to be present to Elizabeth's wisdom and honesty in this hour. With great candor and compassion, Elizabeth shares stories that will touch every listener, regardless of whether or not they've experienced addiction. Conversation topics range from chronic perfectionism (to the point of embellishing truths for the sake of being "enough"), being honest with yourself about what you want, religion's role in life and recovery, and the 2024 NYC Marathon.

On today's episode on Sunday Questions, Cailin and Sam recap their races at the 2024 TCS NYC Marathon last Sunday. This episode covers truly every detail of Cailin and Sam's training and race weekend, complete with listener questions covering everything from carb-loading to travel logistics.

On today's episode, Cailin is joined by dear friend, Fiona Neville - AKA @freetobefi, to discuss all things post-grad life. Though, the concepts in this episode are applicable at any time of life. Hear Cailin and Fiona discuss showing up as themselves in corporate settings, navigating cognitive dissonance in your career, value-based decision making, and how to stop treating ourselves like projects. Fiona is PURE magic.

On today's episode, Cailin has on her boyfriend & favorite person, Sam Frank, for his second unfiltered conversation on Sunday Questions. Topics include: how their relationship has changed since the last time Sam was on the podcast, what planning for the future looks like when you're in a serious relationship in your 20s, and Sam's advice on pursuing graduate studies. Digressions include: Sam's passion for golf, what kind of sea animal Sam would be, and Cailin's kitchen habits.

Welcome back to Sunday Questions for our second season! After 6 months away, Sunday Questions is back. In today's episode, Cailin discusses all things post-grad life, including where she's living, what she's doing, her relationship, and her qualms with corporate America.

On this week's episode, Cailin sits down with Hannah Folau to talk about everything ranging from processing intrusive thoughts, to burnout, to finding purpose as a college athlete. Hannah is the host of the With Intention podcast, and an alumni of Georgetown University, where she played on the Women's Lacrosse team. She's now pursuing her Masters degree at Georgetown's Graduate School while working full time at the Elizabeth Glaser Pediatric AIDS Foundation. Simply put, she's ridiculously impressive and brings the wisdom and perspective like no other.

In today's episode, Cailin sits down with sisters Ellie and Hannah Gerson to talk through everything from postgrad life, or moving across the country, to navigating a heart-wrenching breakup. Ellie and Hannah are among the wisest, most honest guests that Sunday Questions has had the pleasure of welcoming - we know you'll love this one. Find Ellie & Hannah on tiktok, and if you're in NYC, check out Ellie's ice cream brand, Ellie G's!

On today's episode, Mary Rojack (@livingwmary) joins Cailin for a conversation covering everything from eating disorder recovery, all the way to college sports, and making the decision to leave college for a semester to focus on your mental health. Cailin and Mary are, quite simply, cut from the same cloth and found so much mutual love and admiration for one another in this episode.

In today's episode, as Cailin approaches her college graduation in just a few months, she shares 10 lessons she's learned during her time in college. Lessons range from finding humility in your education to learning what's best for you.

In today's episode, Cailin opens with a guiding question: "What the f*ck do I want out of 2024?" which leads into a conversation about what to do when your future lacks clarity, gaining perspective on the finite nature of life, writing your own hypothetical obituary, her post-grad perspectives, and finding joy & meaning in the life stage that you’re in right now.

In the first episode of 2024, Cailin kicks us off with a conversation complete with the things she won't be doing this year, her own iteration of 75 hard that she's calling "75 best for you", and a brief life update in which she cries about change and the evolution of leaving her college sport behind. It's a new stage of life and it's a new stage of Sunday Questions :') welcome back

In today's episode, Cailin shares about her own relationship with intimacy, both physical and emotional, and the things she's learned from negative intimate experiences. Broken into three chapters: emotional, physical, and relationship intimacy. Included in this episode are conversations about feeling self conscious during intimate moments, overcoming emotional barriers, and finding validation for your own negative experiences. TW: This episode includes discussions of sexual assault.

In today's advice session, Cailin gives a recap of her Thanksgiving break complete with advice on spending time with your significant other's family and resolutions to stop letting the behavior of random strangers determine our moods. This week's advice session covers a variety of things from long distance tips to our relationship with intimacy, all the way to career crises and LinkedIn advice. Enjoy!

In today's episode, Cailin recaps the days leading up to the 2023 New York City Marathon, the race itself, and answers listener questions about training, racing logistics, gear, and general motivation.

In this episode, Cailin recounts the five lessons she learned from training for the 2023 New York City marathon. From transitioning to eating animal based protein for recovery, to overcoming limiting beliefs about hard work, and the importance of finding your "why."

In today's episode, the creator of one of Cailin's favorite TikTok series "This Week in 20-Something-Hood" joins Sunday Questions to talk about his creative process, sobriety, the grief of losing a friend, vulnerability as a man, and the inspirations behind the content he's creating. This is not one to miss!

In today's episode, Cailin talks about the lessons she's learned over the past few weeks of experiencing life in full. The conversation spans hopes and dreams, appreciating where you are while you're there, coping with grief, finding community, and living alongside the paradoxes inherent in life.

In today's episode, Cailin talks about how the pressure to interpret a "gut feeling" or "tap into your intuition" is unproductive for people who experience anxiety. In this conversation, Cailin covers learning to live alongside uncertainty in a relationship, the power of feelings, and why the term "gut feeling" has taken on an inaccurate, confusing definition.

In today's episode, Cailin offers listeners her recipe for changing their life. From podcasts to listen to, books to read, foods to eat, habits to implement, and things to avoid, this episode gives listeners looking to change their life a prescription for exactly how to do it. Other tangents include: Cailin's weekly REPORT, chatting about personal evolution & and an impassioned tribute to family.

In today's episode, Cailin responds to listener write-ins for another Sunday advice session. Complete with an unnecessarily long life update to kick off the episode, this conversation covers all things ranging from long distance relationship tips to dealing with imposter syndrome, work life balance, dating, small talk, and finding your authentic self in college.

In today's special episode, Cailin is sharing the most raw account of her mental health journey to date in an interview with filmmaker Jay Devore at the Release Recovery office in New York City, filmed this past spring. Unedited and with video footage, this episode covers Cailin's story of mental health from being a young athlete, to depression, all the way to the unheard aspects of her sobriety and how she found her own self development journey along the way. Thank you to Jay Devore, Grace Adams, Johnny Zhang and the team at Release Recovery for this beautiful archive of growth.

In today's episode, Cailin's back with a solo episode filled with life updates from her summer, feelings about being back at school for her senior year of college, and some exciting career news. Topics include: processing overwhelm and communicating through change, being selective with the "yes's" you give out when you're in a transitory period, understanding how full you like your plate to be, utilizing your weekends, and Cailin's personal favorite concept, The Cubby Audit.

In today's episode, Cailin interviews a dream guest of her's: Sarah Levy, author of Drinking Games. Part memoir and part social critique, Drinking Games is about how one woman drank and lived— and how, for her, the last drink was just the beginning. On paper, Sarah Levy’s life was on track. She was 28, living in New York City, working a great job, and socializing every weekend. But Sarah had a secret: her relationship with alcohol was becoming toxic. And only she could save herself.Drinking Games explores the role alcohol has in our formative years, and what it means to opt out of a culture completely enmeshed in drinking. It’s an examination of what our short-term choices about alcohol do to our long-term selves and how they challenge our ability to be vulnerable enough to discover what we really want in life. In today's episode, Sarah and Cailin cover telling your sobriety story, red flags in your relationship with alcohol, sober dating, growing out of dishonesty, and creating a sobriety toolkit.

In today's episode, Cailin interviews Lily Nikias (@seeing_lily) about moving to Australia at 22. This conversation covers a number of topics ranging from Lily's decision to follow a gut feeling, initiating friendships, intentionally using social media, and just being a generally self aware person. Lily is brilliant, lovely, and the easiest person to talk to -- we're so excited to bring her to Sunday Questions.

With an impending 21st birthday later this month, Cailin recounts the twenty lessons she learned during her twentieth year of life. Topics of discussion range from the thing she struggled with the most this year, to the time she ghosted her boss, all the way to overcoming anxiety around meeting new people and accepting the ever-flowing tides of friendship.

In today's episode, which listens not unlike a therapy session without a qualified therapist, Cailin breaks down her own fears and limiting beliefs. Topics range from being vulnerable to uncertainty and volunteering ourselves to uncomfortable emotions, to Cailin having revelations about her confusing relationship with hard work. Complete with submissions of listener fears and limiting beliefs, this episode is meant to remind us all that self-doubt isn't unique and creating your dreams is a choice.

In Cailin's favorite episode yet, per many requests of the podcast listeners, we have flower boy (formally known as Cailin's boyfriend, Sam) on the podcast. In this episode, Cailin and Sam chat about all things relationships, ranging from the unique story of how they met, to how they intentionally create intimacy in their relationship, to setting precedents in the early stages of a relationship, all the way to Sam's perspective on vulnerability, and his wellness routines. Episode highlights include: rapid fire questions for Sam, profound conversations about Sam's mustache, Cailin attaining Pierogi status, Sam's napping habits, commentary on the "if he wanted to, he would" phenomenon, and Sam giving the podcast listeners some behind the scenes access to Cailin's messy closet.

Straight from the notes app, today Cailin is sharing a list of bullet points describing aspects of her personality that you probably wouldn't get from her social media. Highlights include: a dramatic reading of letters Cailin wrote to her parents as a child, high praise for tortilla chips, and Cailin's inability to dress appropriately for the weather.

To kick off the summer, Cailin had a month long crisis about her appearance. Here's her actionable steps to get out of a confidence funk.

After wrapping up her third year in college, host Cailin Bracken shares her insights on ten lessons she learned throughout the year. Topics include: moments of growth and healing, embracing the idea that life doesn't owe us anything, approaching conflict productively, and knowing when to let go. Especially fun podcast highlights include but are not limited to Cailin discovering that she's a people pleaser, a potentially annoying amount of content about relationships, and a hefty life update about why Cailin was MIA for the past four weeks. We're back, happy Sunday folks :)

In today's advice session, Cailin responds to your write-ins. Topics include heartbreak, body image, establishing good habits, navigating your 20s, finding your routine in college, among other things. Enjoy!

On this week's episode, Cailin is joined by two dear friends who happen to be sisters: Blakely and Savannah Spoor. The creative minds and eyes behind @madison.spain on Instagram and writers of Cailin's favorite newsletter, Blakely and Savannah Spoor are some of the most interesting, dynamic, and grounded people you could possibly spend an hour listening to. Today they're on the podcast talking about all things college life and how to tailor your college experience to work for you, creating a life outside of being a student, as well as their relationship with privacy, social media, and the farmer's market. Tangential conversation topics among this trio include: Cailin realizing she will never be as mysterious as she dreams of being, what kind of pastry they would be, and a plea for Savannah to open up her own restaurant.

In today's episode, Cailin talks about all things timelines, and more specifically her qualms with them. This episode examines how we understand the future, why we're constantly rushing towards a perceived finish line, and how we can re-center ourselves in moments of indecision by asking one simple question. Casually compelling conversations in today's episode include: dealing with post-grad career anxiety, how to approach milestones in relationships based on feelings rather than timelines, why having to play "hard to get" is usually a red flag, and how to cope with the pressure of going into an unpredictable career path. In true Sunday Questions fashion, the episode begins with a lengthy life update complete with Cailin's current obsessions and fixations, her summer plans (completely unsolicited but strap in), and ends with a bonus section of her April intentions.

In today's episode, Cailin breaks down her experience with anxiety and shares the tools she's learned to cope with moments of anxiety, panic, and uncertainty ranging from mindset reframes to taking medication. Cailin discusses the valuable lessons we can learn from the things we have anxiety about, how OCD taught her to be comfortable living alongside life's uncertainties, anxiety and anxious attachments in relationships, and how to decipher a gut feeling from anxiety.

In today's episode, Cailin is joined by her mom, Meghan Bracken, as they discuss a variety of topics centering on healing parent-child relationships and how we can better understand and communicate our needs with our caretakers. Cailin and Meghan discuss the evolution of their own relationship as mother and daughter, and how they navigated their way out of constant contention and into meaningful friendship defined by mutual respect and communication.  Casually compelling conversation topics include: getting curious about our parents as individuals beyond their parenthood, how to approach conversations about therapy and addiction with parents who are resistant to introspection,  and staying connected with your parents as you get older. Casual but not nearly as compelling conversations include Meghan sharing Cailin's childhood absurdities and a game of "who knows who better?" to finish off the episode. 

In today's solo episode, Cailin comes back from her week and a half long hiatus (unthinkable) to provide a twenty minute life update that absolutely nobody asked for.  Though it sounds more like a voice memo to a friend than a podcast episode distributed on globally accessed streaming platforms, this episode is a special one. Topics range from: Cailin's recent trip to Washington D.C. to meet with congress, to letting the most evolved version of yourself lead the way in life, all the way to creating emotional intimacy and buying paper towels before you run out. Not profound, just casually compelling per usual. Happy Sunday!

On today's episode, Cailin is joined by guest and dear friend, Fiona Neville. A writer, blogger, and self-development extraordinaire, it was only matter of time until Fiona made her appearance on Sunday Questions. In this episode, expect detailed discussions on how to live a sexy life (a favorite word of both Cailin and Fi's), Fiona's decision to give up social media for forty days, and why we can all benefit from leaning into the phases we go through. Bonus: speed round questions and Cailin consistently forgetting that she's recording a podcast and not just having coffee with Fiona. 

In today's belated-valentine's day special, Cailin talks about all things romantic relationships. Topics range from things Cailin has learned via flopping in her own relationships, things that keep us from finding an authentic partnership, things that Cailin believes are critical for achieving longevity in relationships, and why comparison kills relationships. Highlights include: an advice session based on relationship-based questions that listeners contributed, Cailin rating red flags based on a scale of one to egregious, a petition to appreciate The Talking Stage, and how to tell when someone is worth ruining your sleep schedule for. 

In today's episode, Cailin finally shares the '23 Habits in 2023' list that she's been alluding to in the past three episodes. Complete with habits ranging from "I will not say goodnight to a man who is not my blood relative unless he is my boyfriend" all the way to starting a high yield savings account and automating your savings. Notable topics include: Cailin airing grievances about people who don't smile back at her on runs, Matthew McConaughey dropping wisdom about leaving metaphorical crumbs, the futility of complaining about the weather, why you shouldn't rush something if you want it to last, the 2 minute rule, and a tactic to help you minimize your emotional  and energetic engagement in gossip. It's never too late to start on new habits, and there's 23 of them to choose from in this episode. Cheers to another Sunday. 

In part one of today's episode, Body Image, Eating Disorder Recovery & Eating for Your Gut, Skin and Brain, Cailin discusses her own (rich) history with disordered eating and poor body image, among other things. This episode follows Cailin's experience with an eating disorder beginning at age 10 and transitioning into her later teenage years, throughout which she confronted her relationship with food and her body, and began to understand the roots of why so many young adults in particular are susceptible to disordered eating habits and poor body image during these formative years of their lives.  Notable moments include: A direct address to the type of parents who talk about their children's bodies as though they're cuts of meat, complete with Cailin "raising her voice", the phenomena of unnecessary eliminations in the modern "wellness" diets, how your metabolism actually works and why skipping meals isn't going to help you, why your gut is like a snowflake, and finally, the impactful question of "how am I to maintain this ass without proper nutrition?"  There's plenty to learn, loads to reflect on, and compelling conversations to be had. Welcome back to Sunday Questions. The blog post referred to in this episode

In this episode, Jumpstarting Your Personal Evolution: Lessons That Took Me 20 Years to Learn & Perspectives That Changed My Life, Cailin sits down and shares lessons she's learned, pieces of advice she's acquired, and perspectives on the human experience that have changed her life forever and have been living in her notes app ever since. There's no gatekeeping on Sunday Questions, so this advice is essentially Cailin welcoming listeners into her notes app and thus into her subconscious. In this episode, expect to be inundated with pieces of advice that are separated only by jarring transitions in which Cailin says "NEXT" in various accents and shrill pitches (she is still, as it turns out, tone deaf). In addition, you can expect to hear impassioned monologues on why you belong in your dreams, how jealousy is your greatest tool to discovering what you want, and Cailin pitching a recipe group for all of her pasta-thrower listeners.

In today's episode, Cailin talks through the evolution of her relationship with alcohol and invites the audience into the conversation by way of a Q&A in which Cailin speaks to aspects of being sober as a young adult, offers advice, and shares what she has learned over the past year and a half+ of sobriety. In this longer form episode, topics range from navigating dating and romance in sobriety to Cailin telling stories like the time she (elegantly) (drunkenly) plummeted down a flight of stairs in downtown Nashville and woke up with the scars to prove it. The episode breakdown goes as follows: Cailin sharing her history with alcohol consumption and how she decided to be sober (her awakening moment involving Tostitos and Vanilla ice cream), the concerns she had about being sober in college, how sobriety has changed her life in ways both challenging and enchanting, her own motivations for ditching alcohol, the mental and physical health benefits of sobriety, and finally a Q&A that covers topics ranging from being the child or relative of an addict or alcoholic to practical advice on how to drink responsibly. More exciting tangents cover: drunk texts, false confidence, and Cailin's run in with a local juvenile court. Sober, sober curious, or none of the above, this episode is for you and is entirely free of judgement. Your journey is yours and yours only.  As promised, resources alluded to in the podcast:  Sober Curious by Ruby Warrington  Huberman Lab Episode on What Alcohol Does to Your Body, Brain & Health  HOP WTR Non-alcoholic adaptogenic beverage (free shipping for dry January!)  Addiction recovery resources:  SAMHSA's National Helpline https://findtreatment.samhsa.gov 1-800-662-HELP (4357) TTY: 1-800-487-4889 Website:  www.samhsa.gov/find-help/national-helpline https://www.findtreatment.gov Also known as the Treatment Referral Routing Service, this Helpline provides 24-hour free and confidential treatment referral and information about mental health and substance use disorders, prevention, and recovery, in English and Spanish.

In today's episode, Cailin brings on guest and dear friend Miranda McKeon to discuss social dynamics regarding the life of an influencer. Cailin and Miranda discuss why so many people are afraid to start being vulnerable on their primary social media accounts, how to start showing up authentically online, why nobody is actually looking at you like you probably think they are, and the fact that you can't wait for a magic fairy to tap you with a wand and suddenly make you "ready" to show up as your most authentic self online or in your life. Regardless of whether or not you're someone interested in pursuing a career on social media, this episode contains lessons in vulnerability that are applicable to every area of life. Plus, if you are interested in growing an online following, this episode contains practical and approachable tips for doing so. In true Sunday Questions fashion, this episode explores numerous tangents including: a proposed double date with Jason Bateman and Will Arnett at Olivetta, how we rang in the New Year with an ear-piercing jingle, and Miranda randomly transitioning into various accents without warning. Enjoy! Miranda's socials:  Instagram Tik Tok  Blog