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.