How To Fail With Elizabeth Day

Episode: How To Date - How to Cope with Heartbreak and Rejection

Date: March 17, 2025
Host: Elizabeth Day
Co-Host: Mel Schilling
Guest: Michelle Elman (Life Coach and Author)

Episode Overview

In this emotionally resonant episode, Elizabeth Day and Mel Schilling tackle the raw and universal topic of heartbreak and rejection in modern romance. Joined by acclaimed life coach and author Michelle Elman, the episode delves deep into the shock, pain, and eventual growth that comes from relationship loss—whether through breakups, betrayal, or divorce. Through candid storytelling and practical advice, the conversation explores the unique trauma of romantic loss, the process of self-forgiveness, and the empowerment that can emerge from vulnerability, even when it hurts.

Key Discussion Points & Insights

1. The Shock of Heartbreak

• Michelle’s Betrayal Story (06:43–10:44)

  • Michelle recounts her engagement ending abruptly after a follower informed her of her fiancé’s infidelity just an hour after she announced their engagement on Instagram.
  • She describes profound shock:

    "I've never really had anything like this, where I couldn't eat, I couldn't sleep." – Michelle (06:43)

  • Importance of trusting your own experience: her family and friends also trusted her fiancé, intensifying the betrayal's pain.

• Survival Mode in the Immediate Aftermath

  • Michelle highlights the importance of taking things "one day at a time" (09:08) and the necessity of not rushing decisions during the shock period.

2. Processing Pain and Beginning to Heal

• Conflicting Emotions After Betrayal

  • Michelle experienced gratitude and relief before anger or sadness took over, noting that trauma needs time to settle:

    "The thinking around trauma is that it takes about three months to settle in." – Michelle (08:01)

• Initial Steps: No Contact & Space

  • Both Michelle and Elizabeth endorse blocking the ex and enforcing a period of no contact to aid healing:

    "You don't get that access to me anymore." – Michelle (18:56)
    "Although it was harder, the blocky and no contact was probably the better one for me." – Elizabeth (19:08)

  • Mel emphasizes the need to sometimes block the ex’s friends for extra space (19:32).

• Coping with Loneliness and Loss

  • Michelle candidly discusses missing her ex’s family and the loneliness that accompanies not just loss of a partner, but also of companionship and routines:

    "The loss of the companionship was a really big thing...it was my best friend. It was my family." – Michelle (22:36)

  • Elizabeth echoes the difficulty of the day-to-day:

    "You wake up in the mornings and your first thought is to roll over and your partner will be there. And then you remember..." – Elizabeth (24:35)

3. Reclaiming Self & Moving Forward

• The Power of “Rebound” Dating

  • Both Michelle and Elizabeth advocate for reframing and embracing casual dating after heartbreak:

    "Let's reclaim the word rebound… it can be so positive and therapeutic." – Mel (15:11) "It was the hope I needed. It was reclaiming my sexuality after… trying for a baby." – Michelle (14:02)

• Dealing with Age-Related Fears

  • Michelle speaks to the anxiety of starting over at age 30 when she’d planned to become a mother, ultimately realizing:

    "Single is better than a bad relationship. And…it's better to not have a kid than have a kid with a father who… will not be a good role model." – Michelle (15:43)

• Building Self-Esteem Post-Breakup

  • Michelle and Mel discuss the importance of self-kindness and the pitfalls of self-blame:

    "One of the hardest things is about the way we treat ourselves now." – Mel (25:53)

  • Michelle recommends her signature exercise: writing 100 reasons why you're dateable (20:18, 42:45).

4. Finding Meaning and Growth in Loss

• Reframing Heartbreak as Opportunity

  • Elizabeth and Michelle stress that breakups, though agonizing, can precipitate growth:

    “There will be some sort of meaning within the dirt and the confusion and the loss and the heartbreak. Just have faith that at some point you will find some glimmer of meaning.” – Elizabeth (36:10)

• Post-Traumatic Growth and Forgiveness

  • Forgiveness is highlighted as a crucial aspect of moving on:

    "There has to be an element of forgiveness because that is a function of letting go." – Mel (33:08) "I forgave him immediately. But this can't work. There's no trust, there's no respect, there's no any of it." – Michelle (10:44, 34:07)

  • Michelle distinguishes between forgiving the person and accepting their flawed actions:

    “He loved me to the best of his ability. And it’s on him that he didn’t improve that behavior. It’s on him that he wasn’t honest with me.” – Michelle (34:31)

• Heartbreak and Parenting

  • The conversation acknowledges the added complications of breakups with children involved:

    "For parents out there who are listening…that message about some self compassion becomes even stronger." – Mel (40:32) “The co-parenting that I have seen done most effectively is one where the two people involved … always center their children.” – Elizabeth (41:01)

Notable Quotes & Memorable Moments

• “One day at a time…even just one hour at a time.” – Michelle (09:08)
• “You can still love someone even when they betray you in the worst possible ways.” – Elizabeth (11:50)
• “If you get up, you’re telling yourself you’re not worth that time. So I sat there…I deserve these four hours.” – Michelle, on the 100 reasons exercise (43:16)
• “You don’t get that access to me anymore.” – Michelle, on post-breakup boundaries (18:56)
• "Rebound…can be so positive and therapeutic." – Mel (15:11)
• "Trampolining is fun—as long as you're wearing a good bra." – Mel, humorously reframing 'trampolining' as a metaphor for bouncing back after heartbreak (15:22)

Detailed Timestamps of Key Segments

• Main Interview Begins / Introduction of Michelle Elman
  [05:03]
• Michelle Describes the Initial Shock of Betrayal
  [06:43]
• Discussion on Trauma and Survival Mode
  [08:01]
• Michelle Details Immediate Aftermath: No Contact, Deciding to Solo Travel
  [09:46]
• Block the Ex: The Value of No Contact
  [18:43]
• Rebound Dating and Sexual Empowerment
  [14:02–15:22]
• Age, Motherhood, and Redefining Life Goals After Loss
  [15:43]
• Self-Kindness, Self-Esteem & The '100 Reasons' Exercise
  [20:18, 42:45]
• Processing Practical Day-to-Day Loss (Loneliness, Missing Companionship)
  [22:36]
• Opportunities in Singleness: “Hot Girl Summer”
  [28:46]
• Post-Traumatic Growth, Forgiveness, Letting Go
  [33:08]
• Reflections for Parents and Co-Parenting After Breakup
  [39:48]
• Weekly Exercise: 100 Reasons Why You’re Dateable
  [42:45]

Weekly Exercise Assignment

Michelle's "100 Reasons Why You're Dateable" (42:45–43:45)

• Write a list of 100 reasons why someone would want to date you.
• Do this in one sitting, even if it requires hours.
• The exercise helps fortify your self-worth, ensuring external events (breakup, rejection) don’t redefine your value.

Overall Tone

The tone is warm, empathetic, and vulnerable, balanced with humor and hope. Elizabeth and Mel are open about their own failures and heartbreaks, never speaking from a “smug married” perspective, but from solidarity with listeners who are suffering.

Summary for Listeners

If you haven't listened to the episode, expect an honest, compassionate exploration of heartbreak. You’ll find actionable advice, validation for your feelings, and stories that show not only can you survive romantic loss—you may even come out stronger, braver, and more yourself than ever before.