Overthinking About Weddings

Why do we feel guilty when we haven’t actually done anything wrong? This week, Amanda overthinks guilt with psychiatrist Dr. Jennifer Reid (@jenreidmd) , author of Guilt-Free: Reclaiming Your Life From Unreasonable Expectations. They unpack the difference between guilt that helps us repair something and guilt that tells us we’re never doing enough, plus the sneaky way it can make us feel responsible for things we can’t actually control. Then, listener thought spirals, like: moving away from aging relatives, feeling guilty for being too tired to enjoy nature, and more. Maybe the goal isn’t to get rid of guilt entirely, but to figure out whose expectations you’re carrying. A spiral about guilt, control, impossible expectations, and letting your own needs count.

If your trauma helped shape who you are, what happens to you when you start healing it? This week, Amanda is joined by complex trauma expert, therapist, and NYU adjunct professor Dr. Gillian O’Shea Brown, LCSW (@dr.gillianosheabrown), author of Psyche’s Awakening, to untangle some of the questions that tend to get flattened into therapy-speak online. They overthink the difference between acute and complex trauma, why certain songs can send us straight back into an old emotional reality, whether being cheated on can be traumatic, and how to know if you’re actually processing your pain or just overwhelming yourself all over again. They also get into closure fantasies, talking to the parent who hurt you, the strange ways old wounds can become ambition or perfectionism, and the fear that healing might erase the person you fought so hard to become. An eye opening spiral about triggers, coping mechanisms, closure, and becoming more yourself instead of less.

Would you ever date an AI boyfriend? Before you say absolutely fucking not, consider this: plenty of people who swear they’d never have an “AI relationship” are already turning to chatbots for reassurance, emotional processing, difficult conversations, or the occasional late-night spiral. This week, Amanda is joined by Bridget Todd (@bridgetmarieindc), host of There Are No Girls on the Internet and author of Love at First Prompt: AI and the Future of Intimacy, to overthink what happens when technology starts creeping into our most private emotional spaces. They talk about women using AI for romance because dating men feels increasingly hostile, neurodivergent people using chatbots to rehearse human connection, the appeal of a boyfriend who literally never gets tired of talking about books, and the very real misogyny baked into “girlfriends who never say no.” But in the world of large language models, who gets to own, shape, and profit from the parts of us that feel most intimate. An inquisitive spiral about loneliness, desire, digital intimacy, and who gets access to our inner worlds.Further Listening: Love at First Prompt by Bridget Todd

What if you actually get your dream job... and then realize you're not living the dream you thought you would? This week, Amanda is joined by Cherie Brooke (@cherie.brooke) and Jean (@_jeanluo), hosts of the Tiger Sisters podcast (@tigersisterspodcast), who both left impressive corporate careers after discovering that the jobs their younger selves would have killed for no longer fit the lives they wanted. Together, they overthink golden handcuffs, the privilege built into pursuing passion, and why a job doesn’t have to provide purpose, identity, money, joy, and self-actualization all at once. They talk about taking sabbaticals, experimenting before making a giant career leap, letting yourself “fade in and out” of ambition, and why a perfectly good job that pays the bills might actually be part of your dream life. A thoughtful spiral about ambition, career pivots, and building a dream life instead of obsessing over one perfect job.Further Listening: Tiger Sisters Podcast

We say we want more human connection, so why can texting “want to hang?” feel weirdly like begging? This week, Amanda is joined by ICU nurse, New York Times bestselling author, and Stories from a Stranger host Hunter Prosper (@hunter_prosper), whose work interviewing strangers has taught him that connection often starts with something deceptively simple: actually listening. Together, they overthink why we assume we’re burdening our friends, the case for the humble 20-minute “micro hang,” and how to be vulnerable without accidentally oversharing your way into an intimacy level you never signed up for. They also get into our increasingly unrealistic expectations around constant communication, why one awkward social moment probably isn’t being dissected in the group chat, and how many potential friendships die because everyone is waiting for someone else to make the first move.A thoughtful spiral about loneliness, vulnerability, and being brave enough to say hi first.