Be My Own Boyfriend: A Midlife Dating Reset Rooted in Self-Worth
Why I stopped dating men to start rebuilding my confidence - and how it changed everything
Self-worth is the new sexy!
It All Started with a Podcast and a Pattern
After appearing on the Raw Chatter podcast with Vicky Midwood, I stepped back and saw the truth behind every relationship I’d had:
I lived by strong values. I showed up for people. I gave energy, time, care — without asking the same in return.
That wasn’t self-love. That was self-abandonment.
As a recovering people-pleaser with anxious attachment, I led with “Here’s what I can do for you,” instead of “Does this relationship support me?”
That pattern ends here!
“Plenty of Fish” more like Plenty of Red Flags!
Ditching Dating Apps and the Menopause Moment
I tried dating again. I skipped the apps this time — Plenty of Fish felt more like Plenty of Red Flags.
I met someone offline. A few dates in, we talked. He opened up about ageing and prostate health. I listened. I asked questions. I wanted to understand.
Then I mentioned menopause.
His face twisted. One word — and he recoiled like I’d said something shameful.
That was the moment I knew. He could talk openly about his body — but I couldn’t mention mine without making him flinch?
If you can’t talk about real life, it’s not a relationship — it’s a script.
Curiosity and emotional maturity aren’t a bonus. They’re the baseline.
As the fabulous Catherine Gray reminds us in There Unexpected Joy of Being Single:
“Single isn’t better. But it’s definitely not less than either. It’s equally as nourishing and joyous an existence.”
Everything ends and begins with what you believe about yourself!
I Realised I’d Been Dating from Conditioning, Not Confidence
I’d gotten used to:
Mixed signals
Inconsistency
Settling for crumbs
I thought that was normal. It wasn’t.
It was the result of old programming: low self-worth, overgiving, hoping someone would meet me halfway while I ran the whole distance.
But that’s not dating. That’s low self-worth disguised as romance.
“Our early attachment experiences shape our expectations in adult relationships. But awareness gives us the power to choose differently.”
- Attached, Dr. Amir Levine & Rachel Heller
Then, enters Barbara Stanny’s Book Prince Charming Isn’t Coming was a drop-jaw moment:
“Prince Charming, in truth, is nothing more than a projection of our disowned selves.”
“Love yourself. Act like it. Speak like it. Make decisions from it. Practice it until it becomes your default.”
- Love Yourself Like Your Life Depends On It - Kamal Ravikant
And just when I thought I couldn't love this mindset more, John Kim came in hot with this:
“Everything ends and begins with what you believe about yourself. What you believe will determine where you will go and who you will become.”
Committed to Myself First! …..No compromise. No apology.
So I Decided: I’ll Be My Own Boyfriend
This ring finger used to represent waiting. Now it marks a decision - to stay true to myself, my values, and my standards. No more performing. No more shrinking. Just full, honest self-respect.
No more outsourcing my peace to someone else’s behaviour. No more waiting to be chosen.
Instead, I:
Take myself out
Rest without guilt
Meet my own emotional needs
Set and keep my boundaries
Choose alignment over approval
“Love yourself. Act like it. Speak like it. Make decisions from it.”
- Kamal Ravikant, Love Yourself Like Your Life Depends On It
A Tattoo and a New Chapter
I marked the shift with a tattoo: a vine leaf around my ring finger — the finger I used to reserve for someone else.
Now it’s mine. A daily reminder: I belong to me.
As my daughter Abbey once quoted:
“You’re not looking for another half to make you whole. You’re whole. And if you’re lucky enough, you meet another whole.”
- Anya Taylor-Joy, Vanity Fair
And THEN - Taylor Swift walked onto a podcast and straight into my soul:
“You should think of your energy as if it's expensive, as if it's like a luxury item. Not everyone can afford it.”
- New Heights Podcast with Travis Kelce, 2023
My world starts with ME!
Midlife Dating Requires Confidence and Clarity
At this stage of life — menopause, grown kids, career shifts — there’s no space for shallow connections.
We need:
Emotional safety
Mutual understanding
Clear, direct communication
Maisie Hill called this phase “a portal.” She’s right. It’s not the end of youth — it’s the start of clarity.
And because John Kim doesn’t miss:
“A thriving relationship is one in which two whole people come together and do life with each other, not at or around each other.”
What I Know Now
I am not too much
I’m not hard to love
I don’t need fixing
I will not abandon myself again
I’m already whole.
And if I date again, it will be from that place — not from hope, fear, or habit.
Ready to Be Your Own Boyfriend Too?
If you’re done ignoring red flags, questioning your worth, or dating from scarcity — start with this:
🎁 Download the free guide:
Date From Your Values: A Self-Worth Reset
What’s inside:
A self-worth check-in
Red flag / green flag checklist
Prompts to define your dating standards
📩 Get instant access → [Download the guide]
Let dating feel different — because this time, you’re choosing yourself first.
🎶 The Soundtrack of Self-Worth
To mark this new chapter, I’ve created a Spotify playlist: Be My Own Boyfriend — a collection of tracks that reflect the strength, softness, and clarity of choosing yourself first.
One song stands out: “Be My Own Boyfriend” by Olivia Dean.
It says what I now live — that self-love isn’t a backup plan. It’s the baseline.
▶️ Listen on Spotify - Be My Own Boyfriend - Let it remind you: you’re not waiting to be chosen.
You already are. a collection of songs that echo the power, softness, sass, and soul of choosing yourself first.
You can listen to it here on Spotify and let the music hold you, lift you, and remind you: you’re already whole.
Happiness begins within.
🌱 Download my free guide: “Date From Your Values: A Self‑Worth Reset”
💬 Follow on Instagram: @nicky_massey_coach
🌿 Book 1:1 coaching: www.nicky-massey.com
📚 Further Reading & Recommended Books
Here are some powerful reads that helped shape my thinking - and may support you on your own journey of healing, self-worth, and midlife confidence:
💖 Relationships, Attachment & Boundaries
Attached – Amir Levine & Rachel Heller
Love Yourself Like Your Life Depends On It - Kamal Ravikant
Single On Purpose - John Kim
🌿 Menopause & Midlife Empowerment
Perimenopause Power - Maisie Hill
✨ Mindset, Self-Worth & Singlehood
Prince Charming Isn’t Coming - Barbara Stanny
The Unexpected Joy of Being Single - Catherine Gray
📚 Yes, I Read A Lot…
Because honestly? It’s way better than being in a relationship that drains your soul - with a man, a woman, or even your past self.
I’m done with breadcrumb love, emotional labour, and second-guessing my worth.
These books helped me unlearn toxic patterns and recognise red flags faster than you can say “gaslight.”
I’m not just healing - I’m upgrading.
And forearmed? That’s empowered. ❤️
Disclosure: Some of the links in this post are affiliate links. This means that if you click through and make a purchase, I may earn a small commission at no extra cost to you. I’m part of the Amazon Associates program, and your support helps me keep creating free content.
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With love,
Nicky ❤️
