With Whit

A Month Together & We Didn't Fight Once: Date Night!

With Whit

Show Notes

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.

More from With Whit

Oct 20, 2026

Hello my friends! How are we this Tuesday? Today, I'm catching you up on life lately and answering your questions. But first, a recap of my experience at the Victoria's Secret Fashion Show, including the vintage dress that got me excited to go and why showing up alone still gets me in my head. Next, an update on my embryo transfer plans and why even the most loving check-ins from people can stir up complicated feelings. Timmy pops in for an unplanned chat about money, work, and figuring out our next chapter. Plus, my current Housewives favorites, getting on the same page with your partner in parenting, which beauty treatments are worth the money and the ones I would skip, and of course, the contradiction I keep coming back to: wanting a quieter life, but worrying I'm not doing enough when I slow down. Thanks for being here and I love you.

Oct 13, 2026

Today I’m sitting down with Clara Sieg, co-founder and CEO of Loonen, to talk about how her fertility journey and becoming a mom led her to question something most of us barely think about: our water. Clara shares how she found a sense of control during IVF through small changes at home, from buying organic food to swapping plastic for glass. But water felt harder to figure out, and preparing formula bottles for her daughter sparked the idea for Loonen. We get into microplastics, why she chose glass for Loonen, and what it was like to go from investor to founder. I still have so much to learn about microplastics, toxins, and what living a little “cleaner” can look like, but this conversation made it all feel more doable and less overwhelming. Start small and build from there. Thank you so much Clara, I love Loonen!

Oct 6, 2026

We're back for a classic Date Night! I’ve been trying to slow down and take care of myself, but I’m also feeling that familiar pull to do more and figure out next projects. We talk about what actually feels restorative, how to know when you're ready to get back out there, and our dream of buying a lake house and documenting the renovation. There are, of course, many detours: whether audiobooks count as reading, why I'd never join Real Housewives, a costly flight-booking brain fart, and airing of grievances. Plus, we get into the difference between getting “the ick” and just “a little icky” and we realize it’s probably time to plan a date night that doesn’t involve microphones.

Sep 29, 2026

I thought having hernia surgery would mean a little forced rest.It’s been a lot more painful and limiting than I imagined, but I'm taking it day by day and figuring out how to slow down and let myself heal. This week, I'm catching you up on the last few weeks: why I’m giving my body more time before our next embryo transfer, my week with Sonny when Timmy was away, NY Fashion Week, some of the sweet and complicated parts of watching Sonny grow up, and how I’m really doing through all of it. It’s a casual check-in from home, where I’m feeling a little down, a little hopeful, and very ready to get moving again.

Sep 22, 2026

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.

See all episodes →