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 preced...

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 ho...

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 unapolo...

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...

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 inter...

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...

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 proj...

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 i...

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 Sch...

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 i...

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 :&#39...

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 valida...

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 LinkedI...

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.