The Dear Twenties Podcast

Ebony Clough started The Dear Twenties Podcast the way a lot of people start writing in a journal, because the twenties were kicking her around and she needed somewhere to put it all. The show reads like letters to herself, and by extension, to anyone else trying to figure out how to be a functioning adult without a manual. Each episode takes on one specific knot: the weird grief of outgrowing friendships, the pressure to have a career figured out by 25, dating when you barely know what you want, what to do when your five-year plan falls apart in month three. Ebony is warm without being preachy, and she tends to sit with questions longer than most hosts would. She brings on guests for some episodes but a lot of the run is just her, talking it through, sometimes changing her mind partway through a sentence. There is no pretense that she has the answers. What she has is honesty about the messiness, and a willingness to say the thing most of us only text our closest friends. After 40+ episodes the archive has real depth now, and certain themes keep circling back: self-worth, boundaries, the slow work of becoming someone you actually like. If you want a show that treats your twenties like a real chapter instead of a punchline, this one is worth a listen.