How To Fail With Elizabeth Day: "How To Date" BONUS EPISODE - Your Dating Questions Answered...

Episode Date: March 31, 2025
Hosts: Elizabeth Day & Mel Shilling

Overview

In this special bonus episode of How To Date, host Elizabeth Day and relationship coach Mel Shilling answer a selection of real listener questions about the complexities of modern dating. From dealing with heartbreak to navigating new relationships with unique challenges (health, age, identity, and more), the episode is a compassionate, nuanced, and often humorous guide to love’s messiest moments. The tone is supportive, candid, and deeply empathetic, with both hosts drawing on experience and research to offer actionable, heartfelt advice.

Key Discussion Points & Insights

1. Learning to Be Open After Hurt

Question from Peachy: How do you become open in dating after many letdowns as a “fearful avoidant, hyper-independent” person?

• Mel's Response (02:31):
  • Acknowledges Peachy’s pain and the complexity of readiness: "Do you actually feel like you’re ready to be open? ...Would you rather spend more time on you?"
• Elizabeth’s Take (03:14):
  • Validates the grief and disappointment, underscoring the importance of taking time to heal.
  • Suggests starting small when re-entering openness: “Start experimenting with small tiptoes into the direction of being more open again,…smiling at someone,…having a chat with the postman.” (04:37)

2. Does Age Matter in Dating?

Question from Kate: Does age matter?

• Elizabeth (05:41):
  • “It doesn’t matter if you fall in love with the person and the context… But it does matter if you are at vastly different life stages.”
• Mel (06:36):
  • Emphasizes “It’s not about age, it’s about stage.”
  • Introduces the “Four Fs”: Finance, Family, Fitness, Freedom—and for fun, Elizabeth adds “Fuckability” and the “Feel Good Factor.” (07:08)
  • Assessment tool: Compare where you and your partner are on each "F" to see if your stages of life match.

3. Do Exes Deserve a Second Chance?

Question from Maria: Should you go back to an ex?

• Mel (09:44-11:17):
  • Recognizes the romantic fantasy but advises realism: "Why did you break up? ...Are the issues that led to the breakup changed?"
  • Warns against “definition of insanity” (doing the same thing, expecting a different outcome).
• Elizabeth (11:17):
  • Counters the “what if” fantasy: “If that relationship were going to work, it would have done. The fact that you’re not in it speaks to me that something went awry.”
  • Notes Brene Brown's quote: “You can have five marriages with the same person.” (12:53)

4. Dating a Same Sex Partner Not Ready to Come Out

Question from Jo: Tips for dating someone not ready to be out

• Elizabeth (13:19):
  • Stresses the importance of loving, clear communication.
  • “Make it very clear that you don’t want to live as a secret in their lives forever.”
• Mel (15:10):
  • Encourages Jo to reflect: “How important is it to you to have a partner who is out and proud with you?... Where does that sit on your priority list?”

5. Judging a Date for Being Early or Ordering First

Question from Anonymous: Is it too judgmental to write someone off for not waiting to order?

• Elizabeth & Mel (15:58-19:51):
  • Reflect on possible deeper reasons (“Is it self-worth, fear of being unimportant, or values clash?”).
  • Mel introduces the concept of tuning out “Family FM”—inherited beliefs from upbringing—and switching to “Me FM”: “Change the station!” (19:19)

6. The Pressure of Finding “The One”

Question from Aish: “I always immediately, subconsciously try to figure out if they are THE ONE.”

• Elizabeth (20:01–21:57):
  • Affirms the impulse as normal, especially for women in their 30s.
  • Warns against letting urgency cloud judgment and silencing “the voice that society has placed in there.”
  • “We have been sold this myth that age diminishes us as women. My experience is absolutely the opposite.”
• Mel (21:57):
  • Applauds self-awareness: “That’s half the battle won!”
  • Advises separating long-term desires from the in-the-moment experience: “Check your self talk. Are you preoccupied with the future at the expense of the present?”
  • On “The One”: “I personally don’t think it’s that helpful. It’s that binary thinking…which can be confusing.” (23:55)

7. Dating After Divorce & Later in Life

Question from Amy: “Dating post-divorce alongside turning 60. Most men of my age want a nurse.”

• Both (24:56–28:05):
  • Mel adds humor: “You don’t want to wipe anyone’s bum. …No kink shaming here.”
  • Discuss dynamics faced by youthful, energetic older daters.
  • Elizabeth reframes: It’s “a blank canvas on which you can paint a different kind of future… get excited about what happens next.” (26:04)
  • Mel’s “dating squad” idea—ask advice from friends of different ages for multi-generational wisdom.

8. Navigating Dating with Children

• Elizabeth (28:05):
  • Advises transparency about kids from the outset: “If someone has an issue with that, they’re not for you.”

9. Dating With a Long-Term Health Condition

Question from Rajeev: How to date with a chronic health condition or catheter?

• Mel (29:56–31:47):
  • Shares her own vulnerability after cancer treatment, reflecting on being authentic: “I would lead with it straight away…Disarming honesty lets people connect with the real you.”
• Elizabeth (32:57):
  • Recommends How To Fail episodes with Miranda Hart and Louise Thompson for further inspiration: “Having an illness is part of you, but it also exists separately from you.”

10. Supporting a Perpetually Single Friend

Question from Talash: How can you support a single friend with bad luck in dating?

• Elizabeth (34:46):
  • Empathy > Sympathy: “Their responsibility is not to package everything up for your entertainment.”
  • Suggests companionship (especially on weekends) and ongoing support beyond their dating stories.
• Mel (36:40):
  • Recalls her own long period of singledom: “Sunday nights were the hardest...including this single friend,... so they feel like part of the group.”

11. How To Kindly End a Dating Relationship

Question from Anonymous: What’s the best way to tell someone you don’t want to see them anymore?

• Mel (37:41):
  • Advocates for “dating karma”: “Give that person the feedback they need to move on and have a more positive relationship next time.”
  • Encourages kind, specific feedback over ghosting.
• Elizabeth (38:33):
  • “You led with love and you ended with love. Every experience is worth something.”
  • Raises dating as community, not a solo pursuit.

Notable Quotes & Memorable Moments

• Elizabeth, on rejection and recovery:
  “Sometimes we never get over rejection or loss. Sometimes it becomes part of us, but… it can be part of us in a really beautiful and helpful way.” (04:37)

• Mel’s Four Fs:
  “If you think about things like finance, family, fitness and freedom…and fuckability, number five.” (07:00)

• On going back to exes:
  “Are you essentially dipping into the definition of insanity by trying to do the same thing and get a different outcome?” – Mel (10:31)

• Mel on giving feedback:
  “Wouldn’t it take a little courage, a little bravery to actually say…‘Things haven’t really worked out the way we had hoped…’” (37:41)

• Both hosts on age and possibility:
  “We have been sold this myth that age diminishes us as women. My experience is absolutely the opposite.” – Elizabeth (21:52)

• Mel on community:
  “Dating is not a solo pursuit and it doesn’t happen within a social vacuum. It’s a community.” (38:48)

Timestamps of Important Segments

| Segment Topic | Timestamp | |----------------------------------------------------|------------| | Addressing openness after repeated hurt | 02:09–05:28| | Does age really matter in dating? | 05:36–08:00| | Should you give your ex a second chance? | 09:38–12:53| | Dating someone not yet out | 13:11–15:58| | Judging a date for being early/ordering ahead | 15:58–19:51| | The pressure of finding “The One” | 19:51–24:25| | Dating post-divorce and at 60+ | 24:25–28:05| | Dating with children | 28:05–28:41| | Dating with a chronic health condition | 29:43–34:36| | Supporting single friends | 34:36–37:16| | How to kindly break it off | 37:41–39:11|

Final Thoughts

This bonus episode brims with warmth, humor, and practical wisdom. Elizabeth Day and Mel Shilling provide perspective on the risks of dating, approaches to vulnerability, and the value of clear communication. The episode concludes by celebrating dating as a shared, community experience, and honors both the challenges and beauty of continued hope in the quest for love.

[End of Summary]