How to Know When It’s Right: The Conversations that Unlock Connection with Lindsay Jill Roth

Many of us have cultivated confidence in our careers, our family life, and our friendships, but when it comes to dating, we feel lost at sea. This was the case for acclaimed TV and live events producer Lindsay Jill Roth, who found herself asking what she knew were the wrong questions in dating (What does he want me to say? How can I make this person like me?). So, she set out to create a tool for herself that she's now sharing with the world. In her new book, Romances & Practicalities, Lindsay offers a roadmap for how to understand your wants and needs better and truly communicate and connect with the person you’re dating, through 250 research-backed questions spread across twelve categories—from money to children to chores to sex. These questions help folks develop deeper intimacy and open up about what they’re looking for in an intimate partnership. In her conversation with Dr. Alexandra, you’ll hear about Lindsay's budding romance with her now husband, the couples she spoke with who have used this system, and the wisdom and practical guidance she’s garnered from the clinical experts she interviewed for the book—including Dr. Alexandra! Lindsay urges listeners to view expansive and thoughtful dialog as something sexy, not just vital, as they get to know someone that they think might be their person. Lindsay and Dr. Alexandra also address a thoughtful listener question at the end of the episode, about dating across socio-economic class.Romances & Practicalities: A Love Story (Maybe Yours!) in 250 Questions by Lindsay Jill RothLindsay’s websiteOrder Dr. Alexandra’s book, Love Every DaySubscribe to Dr. Alexandra’s NewsletterSubmit a Listener Question Join Esther Perel's annual clinical conference Sessions Live 2026! Learn in person in Brooklyn, New York or virtually on May 15th and 16th. Use code SOLOMON50 for $50 off a virtual ticket or SOLOMON100 for $100 off in-person. Get your tickets at https://sessionslive2026.estherperel.com/Learn more about the Options Transition to Independence Program which offers education, vocational, independent living, and emotional support for young adults with complex learning needs. https://www.experienceoptions.org/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.