How To Fail With Elizabeth Day

Episode: How To Date: Taking It to the Next Level

Release Date: March 10, 2025
Host: Elizabeth Day
Co-host: Mel Schilling (Relationship Coach)

Episode Overview

This episode of "How To Date" takes listeners through the pivotal process of taking a romantic relationship to the next level. With no guest joining this week, Elizabeth Day and Mel Schilling draw upon their personal experiences and professional expertise to guide listeners through crucial discussion points: moving from casual to serious, evaluating compatibility, and navigating each other's pasts as you approach a more serious involvement. The episode is structured in three parts, with practical advice, honest reflection, and their signature warmth and humor.

Key Discussion Points & Insights

1. The Transition from Casual to Serious

(Starts ~03:00)

• No Set Rules or Timelines:
  Mel underscores that there's no hard-and-fast rule about when a relationship should move forward. Instead, it’s about clarity and honest conversation.

  "You need to be very, very clear yourself about what that transition looks like... Give yourself the gift of a really smart, clear conversation about the next stage of the relationship." (Mel, 03:10)

• Self-awareness Before Partner Awareness:
  Elizabeth reflects on her past tendency to people-please and move toward relationships out of societal pressure rather than self-knowledge:

  "What wasn’t going on was the question, what do I want? And also, who am I? I don’t think I took the time to understand who I was." (Elizabeth, 04:51)

• Advice for Those Facing Family Timelines:
  Both discuss the unique pressure for women approaching their late 30s who may be considering parenthood, the impact of sunk costs in dating, and how scientific advances (like egg freezing) can offer more options but not perfect guarantees.

2. Honesty & Consent in Defining Relationships

(Starts ~12:14)

• Different Relationship Paces:
  Mel highlights that partners often move at different speeds; bringing awareness and humor to those differences can defuse awkwardness.

  "It's very common for partners to move at a different pace... you can use humour... calling it out for what it is." (Mel, 12:22)

• “The Chat”:
  Discussing how to approach “the chat”, or DTR (Defining The Relationship), and the importance of being honest about what you want, whether that’s exclusivity, exploring non-monogamy, or something else:

  "This is about, as this individual with a sense of self, what does this self need in this relationship?" (Mel, 19:05)

• Consent Beyond Sexual Encounters:
  Mel encourages normalizing “enthusiastic, continuous consent” not just sexually, but for all relationship steps.

  "Consent to move to the next stage of the relationship is also really important to have some agency over." (Mel, 20:27)

3. Exclusivity and Modern Relationship Milestones

(Starts ~23:35)

• Exclusivity’s Awkwardness & Cultural Differences:
  Elizabeth and Mel reminisce about the "childish" feeling of making relationships “official,” and how dating shows (e.g., Love Island) reveal multiple intermediate phases between casual and committed, especially among younger generations.

• Behavioral Signaling of Commitment:
  Mel shares a personal story about her partner acting decisively and “ending things with other people” in an overt show of commitment:

  "He demonstrated it for me behaviorally... He got up from the table, pulled out his phone, made a phone call... ‘I’m just ending it with all the girls that I've been sleeping with.’” (Mel, 26:16)
  Elizabeth: "That’s such a baller move." (26:40)

4. Compatibility

(Starts ~27:08)

• Sexual Compatibility:
  The hosts discuss how sexual compatibility can mask deeper incompatibilities (“drowning in dicksand/clitsand”), and the importance of talking openly about sex:

  "Sexual compatibility can mask deficits in other areas... and I think it's really important to be very open minded at this phase." (Mel, 28:12)
  "Tell me about your most exciting sexual fantasy." (Mel’s conversation starter, 33:46)

• Micro-Cheating:
  Mel defines "micro-cheating" as small, secretive acts of emotional infidelity, often based on deception, and reveals she coined the term:

  "Micro-cheating are those small, seemingly insignificant behaviours that are based on deception..." (Mel, 34:32)

• Three-Pronged Compatibility:
  Mel introduces a simple compatibility framework:

  • Values
  • Lifestyle Preferences (values in action)
  • Deal Breakers

  "Your values are really what get you out of bed in the morning... The highest predictor of compatibility is shared values." (Mel, 36:57)
  "Deal breakers, I think, need to come back to values." (Mel, 38:39)

5. Dealing with Their Past and Your Future

(Starts ~40:14)

• Navigating Emotional Baggage & Jealousy:
  Openness about past relationships and emotional vulnerabilities is key. Mel recommends vulnerability over defensiveness:

  "You can... take action that will push your partner away... or bring them closer... Being able to say to your partner, 'I’m actually feeling a little bit fragile at the moment. I know this is irrational, but I feel some fear with you relating to that person. It makes me feel jealous and I don’t like that that's coming up for me.'" (Mel, 42:36)

• Gradual Disclosure:
  It’s okay to take your time opening up emotional history and past relationships, especially when children or co-parenting dynamics are involved.

  "There’s no rule that says you have to open up your baggage and show what's inside straight away." (Mel, 44:58)

• Blended Families:
  Elizabeth shares her own experience of waiting six months before meeting her partner’s children to ensure stability first.

Notable Quotes & Memorable Moments

• Bum-Sniffing Analogy for Early Dating:

  "I like to think of it like dogs. You know, how dogs sniff each other's bums... That's what new couples do as well, is they're sussing each other out... I’m assessing this potential partner to see if they are going to work for me in my life, not so much whether I measure up for them. That’s their business." (Mel, 05:47)
  Elizabeth: "I already love where this is going. Okay, so you’re advising our listeners just to sniff each other’s bums." (05:56)

• Emotional "Dicksand" and "Clitsand":

  "Have you heard the expression drowning in dick sand? ... And I've definitely seen this with friends and I'm sure I've been drowning in it myself..." (Mel, 28:12)
  Elizabeth: "That now needs to be an expression that I use every single day." (28:28)
  Mel: "Clit sand." (30:02)

• Making “The Chat” Less Daunting:

  "Expanding your comfort zone rather than leaping out of it into restless anxiety is so key." (Elizabeth, 16:47)

• On Values in Dating:

  “Your values are really what get you out of bed in the morning, and they're the things that define what a good life means to you.” (Mel, 36:57)

Practical Exercises & Takeaways

Mel’s Weekly Activity: Values, Lifestyle, and Deal Breakers (47:01)

• List your own and your partner’s values; gauge the degree of alignment.
• Analyze lifestyle preferences: How do both of you enact your values daily? Where are similarities and differences?
• Identify deal breakers—real deal-breakers based on conflicting values, not superficial preferences.

Key Self-Reflection Questions:

• What do I want out of this stage of my life and relationship?
• Are my values and lifestyle compatible with my partner?
• Am I moving at a comfortable pace for myself, or being pushed/pulled by someone else’s expectations (or society’s)?
• Am I clear and honest (both with myself and my partner) about boundaries and future desires?

Segment Timestamps

• Welcome & Series Context: 01:46 – 02:46
• Taking Relationships to Next Level—No Set Timeline: 03:00 – 07:36
• Navigating Parenthood Timelines & Sunk Costs: 07:36 – 10:14
• Egg Freezing & Varied Parenthood Paths: 09:19 – 11:27
• Episode Structure Outline: 12:14
• Getting Serious, When to Quit, “The Chat”: 12:14 – 21:57
• Consent and Safety in Early Dating: 20:15 – 21:57
• Exclusivity & Modern Relationship Progression: 23:35 – 27:08
• Compatibility: Sexual, Emotional, Micro-cheating: 27:08 – 39:07
• Three-Pronged Compatibility Framework: 36:43 – 39:07
• Past Relationships, Emotional Baggage, Dealing with Jealousy: 40:14 – 46:16
• Blended Families & Meeting Children: 44:58 – 46:16
• Weekly Exercise & Close: 47:01 – 48:55

Tone & Final Thoughts

With warmth, wit, and candor typical of the series, Elizabeth and Mel offer both practical strategies and emotionally intelligent advice for anyone hesitant about upping the stakes in modern romance. If you’ve ever hesitated to have “the chat,” struggled with loyalty, or wondered about bringing your past along for the ride, this episode is for you.

Next episode: Handling rejection and heartbreak in a healthy way.