Hotline Date Night is BACK. I am recovering from hernia surgery, Timmy just celebrated his 45th birthday, and we are here by our new fancy bookcase to cuddle up, listen to all your problems, and try to give our best advice. The questions were so good! We get into finding love after starting over, how much your tone matters in a relationship, setting boundaries while living with your in-laws, navigating a child-free family wedding, becoming more vocal in the bedroom, and making space for a partner who has trouble expressing what they need. We may not be qualified, but we certainly have opinions. LOVE YOU.

This episode is brought to you by Sam Edelman.

• Sam Edelman has everyone covered this fall. Visit SamEdelman.com to explore everything you need for fall and get 15% off with code WITHWHIT15

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

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Our kids are growing up in a world that feels faster, louder, and more overwhelming than ever. As Sonny gets older, I find myself thinking more and more about how this world is shaping him and reflecting on the choices I make as a parent. Today, I’m joined by Dr. Shefali for a conversation that made me take an honest look at what it means to raise a conscious child right now. We discuss how technology, social media, comparison culture, and constant overstimulation affect our children’s confidence, connection, and sense of self. She explains why boys and girls may experience these pressures differently and what their behavior can reveal about how they’re really feeling. I also ask Dr. Shefali about some of the things I wrestle with: screen-time boundaries, sharing Sonny online, protecting his privacy, and staying truly present when life feels so busy. We get into why kids need more stillness, play, nature, and face-to-face connection, and all the small actions we can take to help them feel safer, more grounded, and more connected to who they are. Dr. Shefali’s new books, Raising Conscious Sons and Raising Conscious Daughters, offer practical tools for understanding the distinct challenges children face today and a blueprint for helping them grow into connected, resilient, and authentic adults. Thank you so much Dr. Shefali!

This episode is brought to you by Monarch, Sam Edelman, and OSEA.

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half-off at just $50.
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This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hey everybody, welcome back! We are currently out in New York for our niece’s Bat Mitzvah, so today we’re re-airing an episode with one of the BEST, Allison Bornstein. Allison is an incredible stylist who is all about helping people to find their unique personal style inside their own closets. Her style is so cool and effortless. She gives so many tips on how to find a little more joy in getting dressed in the morning and gives all kinds of outfit ideas for different scenarios. AND we also discovered that we were both interns at Teen Vogue. I know you'll love her if you don't already!

This episode is brought to you by Monarch Money:

Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It's Date Night! We're back in our home and Sonny is back to school tomorrow!! We’re talking back-to-school August chaos, upcoming travel, our latest house projects, my hernia surgery, ideas for Timmy’s 45th birthday, and Timmy being the new assistant football coach. Plus all the Date Night usuals, airing of grievances, and a little lesson in trusting yourself. Love you guys!

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello darling people I adore! How are we? I have a chill evening solo for you with a lot of thoughts. I've made some big decisions for myself. I'm making my world smaller and my dreams bigger and it feels good. I feel ready. I dive deeper into my decision to try to carry our baby myself, why I finally feel ready to move forward with our two remaining embryos, and how I'm trying to prepare myself without letting fear or pressure take over. I also get into where I'm at with social media and my career, and why creating content just for the sake of creating content doesn't feel fulfilling to me anymore. I'm trying to figure out what I actually want to wake up and do, not what I think I'm supposed to be doing. And I think I finally have an answer: I want to open a store!!! I share where this dream comes from, how connected it feels to my mom and my childhood, and why creating a space for fashion, connection, and community feels so exciting to me right now.

Lots of life updates, some tears, some rambling, and a lot of figuring things out in real time. Love you all!

This epIsode is brought to you by Monarch.

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50.

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What does it really mean to be part of The Sandwich Generation? This is a really personal one for me and I'm honored to welcome back Jill McNamara, LICSW, Vice President of Senior Care at Care.com and a senior care and aging expert, to talk about the emotional realities of caring for aging parents while raising a family. Following the release of Care.com's first-ever Sandwich Generation Report, Jill shares insights from a survey of 1,000 caregivers, revealing just how common and often invisible this experience has become. Together, we get into why so many caregivers don't recognize themselves as caregivers until they're already overwhelmed, the emotional weight of decision fatigue and anticipatory grief, why asking for help can feel so difficult, and the surprising personal growth that can emerge through caregiving. I open up about what's currently going on as my siblings and I continue to navigate our mom's Alzheimer's diagnosis and all the difficult decisions that comes with it as we figure out the best way forward.

Whether you're currently caring for aging parents or simply want to be better prepared for the future, this conversation offers practical guidance, reassurance, and a powerful reminder that you don't have to navigate caregiving alone.

To learn more, explore Care.com's 2026 Sandwich Generation Report and caregiver resources at care.com/sandwich, and follow @WeAreTheSandwichGen for ongoing support and practical tips. And if you're looking for care for your own family, whether that's childcare, senior care, or anything in between, you can use code WHITNEY35 for 35% off a Care.com membership.

This episode is brought to you by Starbucks:

• At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at Starbucks.com/partners

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Hello hello it's Date Night with Whit with Tim! We are catching up after our Summer in Vermont and might need a little time to process the whole month, but we are sharing some of our biggest takeaways. We get into what it was like living in close quarters with family, how we didn't have a single fight, parenting through the moments when you're about to lose your sh*t, and what we're learning about patience, self-improvement, and letting go of the need to have everything figured out. Plus, Sonny's 9th birthday, our Vermont food faves, Love Island thoughts, and why the journey really is the destination. How wise are we? Happy dating to you and you.

This episode is brought to you by Monarch & Starbucks.

• Write your own money story with Monarch. Use code WITHWHIT at Monarch.com to get your first year of Monarch Core half off at just $50
• At Starbucks, full- and part-time baristas can build meaningful careers, while getting industry-leading benefits. Learn more at Starbucks.com/partners

This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.

Produced by Dear Media.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.