Is he your person, or have you just invested too much time explaining his texts to your friends? Serena Kerrigan joins Chloe to talk dating the same guy in a different font, her three P theory (practice, potential, plot), and what makes “the one” feel so different from the rest. From staying too long to making your boyfriend your entire personality, consider this your guide to investing in yourself, building a life you love, and making room for someone without losing yourself or needing them to complete you.

Get Serena’s book: Let’s F*cking Date

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You wrote in, and Chloe is answering. This week’s inbox includes an ex who became a changed man the second it was too late, a casual fling whose personality disappeared after sex, a bedroom problem no one wants to say out loud, and a bride-to-be who discovered her fiancé had a secret life. Let’s get into it.

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He’s avoidant. She’s projecting. Or maybe they’re just being weird? Chloe sits down with The Psychology of Your 20s host Jemma Sbeg to talk about why uncertainty makes us obsessed, when psychoanalyzing turns into excuse-making, and why understanding someone doesn’t mean you have to tolerate them. Plus: unavailable men, healthy love, and the suspiciously productive power of heartbreak.

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If you want a family someday, it’s almost impossible not to do the math backward and wonder if you’re already behind when you haven’t met the love of your life by 25.

Somewhere along the way, that ticking clock can start creeping into the way women date, the way women leave, and what we're willing to settle for. You might find yourself staying a little too long in the wrong relationship because starting over means throwing the whole timeline back into the unknown.

So this week, Chloe is unpacking the biological clock itself: what actually happens to fertility as we move through our late 20s and 30s, why everyone is obsessed with 35, AMH, egg freezing, and how to have an ideal timeline without letting it become a deadline.

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Today I’m giving you my full dissertation on the chill girl because I have THOUGHTS. She’s low-maintenance, easygoing, never needy, never difficult. But how much of being “chill” is actually confidence, and how much is abandoning your own needs before someone else gets the chance to reject them?

Let’s get into where the chill girl came from, why women are so afraid of being “difficult,” and what it actually looks like to retire her for good.

Articles:

Nice girls don't ask

Sometimes it does hurt to ask

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Koreen built a career and sold millions of games by asking people questions they weren’t prepared to answer. This week, my longtime friend and founder of We’re Not Really Strangers sits down with me to trade the questions that changed our lives.

Somewhere between love, ambition, self-betrayal, and the kind of honesty usually reserved for three martinis in, we get to the answers we’ve been avoiding. Come prepared to ask yourself the hard questions, add a few to your conversational arsenal, and leave knowing yourself a little better.

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I went back through some of my favorite conversations to bring you the best dating and relationship advice, all in one episode. From heartbreak and attachment styles to boundaries, self-worth, communication, and building healthier relationships, these are the lessons everyone needs to hear. I wish this episode had existed when I was in my early 20s...it could’ve saved me years of therapy, lol.

Listen to each full episode:

Amy Chan — bestselling author of Breakup Bootcamp and Unsingle

Sabrina Zohar — relationship coach and host of The Sabrina Zohar Show

Kati Morton, LMFT — licensed marriage and family therapist, author of Are u ok? and Why Do I Keep Doing This?, and host of Ask Kati Anything

Jaci Marie Smith — co-host of the What We Said podcast

Jessica Baum, LMHC — psychotherapist and author of Anxiously Attached and SAFE

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Nobody tells you that falling in love with the right person can unlock a whole new set of fears. This week, we're talking about healthy love, unlearning old relationship patterns, the fear of losing control, and why anxiety doesn't always mean something is wrong.

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Ever wish you could ask the person you're dating what they actually mean? We brought in comedian, podcast host, and author Jared Freid to help decode the behavior driving you and your group chat insane. From mixed signals and situationships to commitment, labels, and all the phrases people use instead of saying what they really mean, we're asking the questions you're too afraid to ask and getting some honest answers.

Check out Jared's new book, Walking Red Flag

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Dessert is delicious. But if it's the only thing on your plate, eventually you're going to get sick. Somewhere along the way, we started treating relationships like the main event. Like life begins when you get the boyfriend, the ring, the wedding, the happy ending.

Meanwhile, we're hurtling through space on a floating rock with entire lives to build, people to meet, places to see, and stories to collect.

Love is beautiful. Love is worth wanting. But life is happening now, not after you find it.

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