The Best (And Hardest) Dating (And Life) Advice You’ll Ever Get
This one shift can change your love life—and your whole life.
This post is about going for broke when it comes to:
Creating the love life (actually, the whole life) of your dreams
Overcoming shame and the fear of failure
Hint #1: If you overcome shame and fear of failure you will automatically create the life–and dating life–of your dreams. This post tells you how.
Hint #2: If you are too busy to read this whole post, scroll down a little to the executive summary and get the gist. But I promise, wading in more deeply will help.
Hint #3: If you love me or like me or just want to encourage me to continue writing, please leave a comment on this post (also, if you really want to support, you can become a paid subscriber by clicking here).
You, Colin? Writing Love Life Advice?!
Here’s what’s really fun → One of my Substack readers left a comment actually asking me to write a post about dating advice.
Guess what?!
I’ve always wanted to write a dating advice column!
It happened because a wonderful colleague named Margo Gantner helped me migrate to Substack in the most marvellous way (message me for her deets). Margo suggested I ask you readers in a previous post what you’d like me to write about.
So I did, and a reader named Johannes wrote:
“I‘d love to read your thoughts about how to find romantic love in a world of online dating, high expectations and little willingness to try and work things out?”
Also, on a different subject, Margo–the same Margo that helped set up my Substack–wrote:
“I‘d love to read more about overcoming shame and fear of failure.”
Interesting, right?
Because ask yourself:
What if a successful dating life–and a successful life, overall–and overcoming shame and fear of failure… were actually the same challenge?
Right?!
A Summary For Those Who Want To Execute
Before we dive in, let me just say:
Never once in the history of humankind has someone less qualified than me been asked to write dating advice!! LOL
And yet!!!
What follows is advice about moving towards things you want that won’t just help your dating life but every other aspect of your life too.
Seriously!
Why do I think so?
Because these are the same principles that have helped me and my coaching clients to expand and grow their lives, organizations and missions. In other words, they’re not just theories. They are ways of being in life that work.
And as promised, in case you’re too busy, here is the…
Executive Summary
Create a vision of your dating life and the rest of your life that makes you so happy and brings joy to you and so many other people too to the point that you don’t care how risky it is to try to get the vision.
Act like the person who gets the dream. Make the play. Ask out everyone you find attractive without inhibition. If they say no, find ways to respectfully persist (or move on). In the rest of your life, ask EVERYBODY for EVERYTHING you want without inhibition.
Ignore discomfort. Ignore shame and fear of failure no matter how uncomfortable they are. (It’s ok, Margo, it is just discomfort that isn’t based on Truth. Also, you are amazing. I really like you!!!).
Reduce resistance to your own happiness. We all have limiting stories about how we can’t and shouldn’t. Surface the stories and reduce them.
Hugely value your own growth. Take this quote to heart:
“Risk is essential. There is no growth of inspiration in staying within what is safe and comfortable. Once you find out what you do best, why not try something else?"
—Alex Noble (artist)
Create A Compelling Vision And Commit
We all have stories about why we can’t have what we want, reasons we can’t try and feelings we don’t want to face in our quest.
Johannes, perhaps without knowing it, has stories about “the world of online dating, high expectations and little willingness to try and work things out.”
Margo gets tripped up by feelings of shame and fear of failure.
But what if we have a vision for a dating life or whole life that is so compelling and you are so committed to it that you cannot be deterred by stories about the dating world or the discomfort of shame?
What if you create a vision you care about more than comfort or fear of failure?
I know of a person who met someone who was the love of their life, but also started out with a belief that that person could never be with them.
My acquaintance created a vision that was so amazing that their perceived high prospect of getting hurt and failing simply wasn’t a deterrent.
The vision began:
“I declare the possibility that I am and believe myself to be one half of the most powerful and awe-inspiring soul partnership that I ever have or ever will witness.”
What possibility could you declare that would keep you undeterred in the face of any challenge?
Johannes, what is a vision so great that you will fight your stories down before giving up? A vision for which you will get up every day and just act committed?
Act Like The Person Who Gets The Dream
My own coach told me about who I have to be in relation to my visions: committed, consistent, confident. That means that nothing that happens is a sign that I should give up. Everything that happens is just information about how I should go about acting committed, consistent, confident.
Be very clear about this. This doesn’t mean I have to feel committed, consistent, confident. It just means I have to act like it.
Johannes, how would you be if you acted like you were sure that you could have the dating life you wanted? Margo, how would you be if you didn’t act from your feelings of shame and fear of failure?
Now, don’t worry if you feel the ways you would need to act. Just put on a psychic costume as though you are those ways and act like it. Be like a stage performer.
How would you approach someone you were attracted to, Johannes, if you were dedicated to being committed, consistent and confident?
Margo, how much less would shame and fear of failure influence you if you acted committed, consistent, and confident?
Of course, being committed, consistent and confident doesn’t fit all situations.
I know of a person committed to meeting a partner and starting a family within a year. The person they have to be is bold and unabashed. Like, talk-to-strangers-and-ask-them-out-in-the-grocery-store bold.
So make a list of characteristics. And let me know in the comments: Who do you have to be to bring your vision?
Then, be it!!
Ignore Discomfort
I know someone who wants to be able to be radically honest. They want to say to a prospective sexual partner, for example,
“I am just coming out of a relationship and I need to feel wanted. I just want you and I to go home and show each other a lot of physical tenderness. Would you be up for that?”
Trying to be bold enough to say that would cause the person I know intense discomfort—but why?
As long as you have consent to ask a question like that and ask it respectfully, why shouldn’t you?
So: What could you do if you just ignored the discomfort you felt?
Byron Katie said that you can have anything you want if you are willing to ask a thousand people. What would stop you from asking them? What false story?
In all of your life, not just your dating life, who would you ask and for what?
Now ask! Ignore the discomfort.
Reduce Resistance To Your Own Happiness
Ok, so this is back-of-an-envelope, write-it-out-on-a-napkin, tap-it-into-your-phone-notes stuff. You don’t have to labor. If you haven’t done it already, quickly write out the amazing vision and the characteristics of a person who would easily achieve it.
Now, write out the ways in which that vision and adopting those characteristics makes you uncomfortable. Or share them in the comments.
Johannes might think: “I can’t approach someone I’m attracted to in a grocery store aisle because I’d feel humiliated.”
Margo might think: “I can’t move without fear of failure because, well, I might fail.”
Once you have the discomforts and stories behind the discomforts written down–notice the constriction they cause in your body.
Now, using that constriction as a compass, rewrite the stories in your mind and look for the story that causes ease and expansion and pleasure in your body.
For Johannes, “There is someone looking for me in a grocery store aisle and I will find them” might be one.
For Margo, “The prospect of failure is a cue that I am moving towards where the greatest opportunities live” might work.
Do this with all your stories. And do it every time an objection to your own vision and life comes up. The stories that cause constriction are out of alignment. The stories that feel easeful and joyful are the ones that are in true alignment with you.
Remember this: ‘Yes’ lives in the land of ‘No.’ You ask 20 people in the grocery story for a date and you get all nos. But the yes that finally comes lives in the exact same aisle–the land of nos.
Johannes: You might be thinking you cannot ask someone out in a grocery store. If you think that, you are right. But what are the characteristics of someone who can ask someone out in a grocery store? Be like a stage actor and act like them.
Hugely Value Growth
So ask me honestly, “Will I get what I want if I do all this?”
Honestly I will answer, “It is more likely, but we can’t be sure. What we can be sure of is that you will grow and expand hugely.”
And guess what?
That’s the real point. Everything we want will come and go.
The person we want to date will leave or die (or we will). The opportunity we chase will eventually dry up. Not to say that we won’t enjoy them in the meantime.
But the real prize? It’s the growth in our ability to perceive in joy and awe, create in magic and gratitude, and see that all of this connects us to Oneness so we want to serve ourselves and others.
I have a client who is actually working on the ask-for-a-date-in-the-grocery-store thing. Does my client have a partner yet? No. But they have taken the same new boldness and used it to ask for speaking gigs and got them.
Another client is showing up as the person they need to be to triple the size of their organization. Have they done it yet? It’s still unfolding. But the personal expansion they’ve stepped into has already earned their kid a full scholarship—and spots on several influential boards.
Plus, the feeling that you are in charge of helping your own life and in charge of helping this whole world is the real prize.
You are not a victim.
You are a creator.
And you are beloved.
You are in grace.
You are already Buddha.
Stop limiting yourself. Challenge yourself to harvest the fruit and share it.
Let’s talk
What’s a bold act you could take that would grow you—even if you weren’t sure of the outcome?
What’s the story you’re ready to rewrite?
I’d love to hear your thoughts. Comment below or reply to this email.
Try This
Today, pick one desire you’ve been hesitating to pursue—whether in dating, work, or self-expression.
What story has been holding you back?
What would change if you acted like someone who was already successful at this?
What discomfort could you ignore for five minutes?
What story would create more ease and joy?
Write it down. Try it. Let it grow you.
Love,
Colin
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PPS. Please also share this post with friends and reStack it.
I saw this recently: "Shame is a bit like mushrooms. It lives in the dark and feeds on bullshit."
Colin, this is the kind of post that lingers. You took two questions—about love and about shame—and showed they might be the same doorway. That’s wild. And kind of liberating.
This line got me: “Act like the person who gets the dream.” So this week, I did. I asked for things: LinkedIn recommendations, help finding more clients, support rebuilding my CV. I even asked my husband to hold a bigger vision with me—for both of us.
Also—honest question for anyone reading: What story does your shame keep telling you, and what might happen if you stopped believing it?