Jenna Williams 6/9/26 Jenna Williams 6/9/26

Episode 24: How Much Should Parents Post About Their Adult Kids? Plus: Should You Pay for the Friends Trip If You Have More Money?

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Jenna Williams 6/2/26 Jenna Williams 6/2/26

Episode 23: How Do You Support a Friend Dealing with Family Estrangement? Plus: Dan Harris Wants Our Advice!

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Jenna Williams 5/26/26 Jenna Williams 5/26/26

Episode 22: Do Adult Children Need to Know About a Parent’s Affair? Plus: Is It Selfish Not to Share Food You Order With Significant Others?

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Jenna Williams 5/19/26 Jenna Williams 5/19/26

Episode 21: Should You Feel Offended If You Can’t Meet Your New Grandchild in Person? Plus: Quitting Without a Backup Plan 

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Jenna Williams 3/24/26 Jenna Williams 3/24/26

Episode 20: Is It Okay to Admit You’re Less Attracted to Your Partner? Plus: Carl Radke Wants our Advice!

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Jenna Williams 3/17/26 Jenna Williams 3/17/26

Episode 19: How Do You Set Money Boundaries with Family? Plus: Save It for Later or Use It Now?

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Jenna Williams 3/10/26 Jenna Williams 3/10/26

Episode 18: Is Your Partner’s ‘Work Wife’ Crossing Boundaries? Plus: Are You Becoming Your Parents?

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Jenna Williams 3/3/26 Jenna Williams 3/3/26

Episode 17: Is It Always Wrong to Give In to Teen Peer Pressure? Plus: The Best Gift You Ever Gave

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Jenna Williams 2/24/26 Jenna Williams 2/24/26

Episode 16: Should You Keep a Dying Parent’s Secret? Plus: Making Peace With Yourself

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Jenna Williams 2/17/26 Jenna Williams 2/17/26

Episode 15: How Do We Help People Grieve? Plus: When AI Starts Mediating Your Marriage

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Jenna Williams 2/10/26 Jenna Williams 2/10/26

Episode 14: Should Your Spouse Tell You If They’re Meeting Up with an Ex? Plus: Valentine’s Day Expectations

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Jenna Williams 2/3/26 Jenna Williams 2/3/26

Episode 13: Should You Cut Ties With a Parent? Plus: Chrissy Teigen Wants Friendship Advice

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Jenna Williams 1/27/26 Jenna Williams 1/27/26

Episode 12: Is Your Partner Too Needy? Plus: Small Decisions That Changed Your Life

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Jenna Williams 1/20/26 Jenna Williams 1/20/26

Episode 11: Should You Call Out an Awkward Problem? Plus: Did We Follow Our Own Advice?

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Jenna Williams 11/25/25 Jenna Williams 11/25/25

Episode 10: What If Your Father Is Having a Baby With Someone Your Age? Plus: David Duchovny Gives US Advice!

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Jenna Williams 11/18/25 Jenna Williams 11/18/25

Episode 9: What Happens When a Grandparent Won't Say No? Plus: Friends Who Are Difficult Diners 

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Jenna Williams 11/11/25 Jenna Williams 11/11/25

Episode 8: Should Parents Stay at Your Place or a Hotel? Plus: Temptation in the Office

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Jenna Williams 11/4/25 Jenna Williams 11/4/25

Episode 7: How to Manage a Dramatic Family Member? Plus: Separating Twice & Staying Together With Mandy Patinkin & Kathryn Grody

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Jenna Williams 10/28/25 Jenna Williams 10/28/25

Episode 6: How Do You Handle a Conversational One-Upper? Plus: Elizabeth Gilbert Has a Question!

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Jenna Williams 10/21/25 Jenna Williams 10/21/25

Episode 5: Why Am I Sad After My Wedding? Plus: The Holiday Season Debate

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