Podcast Summary: My So-Called Midlife — “F the Fairy Tale: Rewriting Love in Midlife with Damona Hoffman”

Host: Reshma Saujani, Lemonada Media
Guest: Damona Hoffman (Dating Coach, TV Personality, Author)
Date: November 19, 2025

Episode Overview

This episode explores what it means to rewrite the narrative of love and dating in midlife, challenging the traditional “fairy tale” ideals women have been taught. Host Reshma Saujani talks with dating coach and author Damona Hoffman about finding fulfillment in relationships at midlife, the realities of dating apps, myths about love, and practical tips for those navigating love the second (or third) time around. Major themes include reclaiming agency, practicing authenticity, and the crucial differences between romance ideals and real-life relationship needs.

Main Discussion & Insights

Midlife: A Time of Transition and Self-Reflection

• Feeling In-Between: Both host and guest discuss the challenges and gratitude that come with being in midlife—managing aging parents, young kids, and new layers of responsibility and self-awareness.
• Bravery and Growth: Damona shares how being a “Black Jewish girl from the Midwest” meant learning to live bravely and authentically from a young age, and how this mindset shaped her approach to love and career.
  • Quote: “I had to live brave. I had to live out loud. ... Is this how I want to be living my life?” (Damona, 04:38)

Busting Myths and Rewriting the Love Story

The Fairy Tale Problem

• Damona’s book, F the Fairy Tale, is not anti-love, but anti-myth. She seeks to empower people to become co-creators in their love stories instead of waiting to be “chosen.”
  • Quote: “I’m actually a co-creator in the experience of my life, in my dating experience, in the relationship that I’m trying to build.” (Damona, 11:23)
• Four main myths are identified, particularly "the list myth"—the belief that a perfect checklist will lead to the perfect match, which often reflects inherited expectations rather than true needs.

Midlife Wisdom and Expectations

• Reshma observes that friends re-entering dating post-divorce are more likely to value being “seen and supported” over status-matching or rigid lists.
• Damona cautions: self-knowledge can come with increased rigidity—people must make space for compromise and practice relationship skills before a partner arrives.

The Changing Landscape: IRL vs. Apps

• Damona draws parallels between her casting-director past and online dating—both require presenting an authentic self (or "headshot") to make a real connection.
• Despite nostalgia for in-person meet-cutes, she encourages embracing current realities—apps are prevalent and efficient, especially for busy women.
• Quote: “I don’t like to spend too much time focusing on what's better. I like to just focus on what is.” (Damona, 09:27)
• The need for clear goals and boundaries applies whether online or offline.

Practical Dating Advice & Key Tips

1. Clarify Your “Must-Haves”

• Narrow down your list of ideal partner traits to just 3 must-haves and 1 dealbreaker. This sharpens focus, breaks with inherited or superficial expectations, and gives you more reasons to say “yes” rather than endless reasons to say “no.” (22:06)
  • Quote: “Going back to the example of the list ... I dig underneath that. And I’m like, why? Why do you need that? Why is that important to you?” (Damona, 22:36)
• Recognize where your expectations come from—real needs vs. family/fairy tale.

2. Move Off Apps Quickly

• Don’t linger in endless texting or DMs. Move to a phone or video call within 1 day to 1 week. This helps avoid scams, emotional fantasy, and false intimacy.
  • Quote: “People are using ChatGPT to write their text messages. There’s a false sense of intimacy that’s developing … get offline as quickly as possible.” (Damona, 23:28)
• Don’t let “dating by text” substitute for actual connection.

3. Keep First Dates Short & Sweet

• Aim for 60–90 minutes, just to check for vibe/connection. The purpose is to see if you want to spend another hour together. Too long drains momentum, especially early on.
  • Quote: “People are spending too long on their first dates. … After three dates, then we start looking for chemistry.” (Damona, 31:24)

4. Protect the Early Phase (“Slow Love”)

• Avoid the rush to integrate new people into your circle, social media, or discuss too much too soon. Give space for natural development and your own internal assessment.
  • Quote: “A lot of times we are in such a rush to get to the end that we try to shortcut it. ... You lose your own internal compass sometimes when you’re taking in too many other perspectives.” (Damona, 33:59)
• Build slow, hold space for magic, and honor your feelings without external noise.

5. Practice Relationship Skills Before Partnership

• Make space for dating in your schedule, set healthy boundaries at work/life, and practice flexibility and compromise. The right relationship won’t arrive if there’s no space for it.
  • Quote: “If you wait to create the space when this person arrives, they will not arrive because they will not see the space in your life for them.” (Damona, 15:58)

The Bigger Picture: Relationship Anarchy & Evolving Norms

Marriage, Partnership, and Loneliness in Midlife

• Damona recognizes that more adults than ever are single, and it’s OK to opt out of partnership or marriage for a season—or permanently. Relational needs change over time.
  • Quote: “If that is what you need right now, don’t feel like you need to rush into another partnership. ... Our life happens in seasons.” (Damona, 44:19)
• The societal expectation for marriages/partnerships to be “everything” (lover, best friend, business partner, co-parent) is unrealistic and contributes to loneliness.
• “Relationship anarchy” means de-centering marriage and recognizing the need for many sources of love, support, and fulfillment.
  • Quote: “It’s a lot of pressure in today’s world for your partner to be your best friend, your lover, your confidant, your business partner, ... So, also invest in other relationships that make you feel loved, supported, and heard.” (Damona, 48:45)

Memorable Quotes & Moments

• On agency: “Stop waiting to be chosen. Choose yourself first.” (Reshma, 53:24)
• On authenticity: “There’s a million people that could do this role, but there’s only one you. And it’s the same with dating.” (Damona, 36:58)
• On the goal of love: “Love is not a reward for perfection.” (Damona, 51:39)
• On partnership: “I believe that relationships are a mirror to teach us more about ourselves.” (Damona, 52:08)

Key Timestamps

• [04:17] Damona’s self-introduction — growing up brave
• [07:02] How Damona became a dating coach
• [09:27] Debate: IRL vs. online dating
• [11:01] Top myths about relationships and women’s expectations
• [14:13] How expectations shift after divorce or with age
• [15:58] Creating space in your life for relationships
• [22:06] How to narrow your “list” to 3 must-haves
• [23:28] Why you should quickly move offline from the apps
• [31:24] Ideal first date duration and expectations
• [33:59] “Slow love” – Keep social circles out of early dating
• [36:58] Authenticity versus auditioning in dating profiles
• [44:19] More Americans are single—embracing choice/seasonality in relationships
• [48:45] Relationship anarchy and de-centering marital partnership
• [52:08] “Happily ever after” as self-growth and reflection

Final Takeaways

• The old fairy tale is dead: Love is not about perfection, rescue, or being “chosen.”
• Rewriting your love story in midlife means acting with agency, authenticity, and grace toward yourself—whether partnered, unpartnered, or somewhere in between.
• Embrace modern tools, but know their limits—move quickly to real connection.
• Intimacy and fulfillment are built through intention, practice, and a wide lens on community and support—not just romantic relationships.
• Happily ever after is recognizing relationships as mirrors—opportunities for deep self-understanding and growth.

Send this episode to your group chat—everyone’s rewriting their fairy tale.

Resources

• Damona Hoffman’s book: F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story
• Damona Hoffman’s podcast: Dates & Mates
• Host: @ReshmaSaujani | Moms First