I wanted to share some stories of how I had to own my standards in relationships, and work through any worthiness issues along the way through the different people I dated when I was single.
I have a lot of stories, and I want to share them to help you, and also so that you know me better and more about what led me to where I am now.
A lot of my biggest lessons came from having to learn what I did not want, to help me get clear on what I did want. Every no and every bad experience helped me to redefine and re-calibrate my standards around love and dating.
Part of why I think I was single so long is that I was meant to go through all of these experiences myself to help me eventually get to the place where I could own what I wanted and call it in, but also because these stories are meant to help others learn lessons from theirs and know when to walk away, and what they might take from each “no” too.
I guess I should take you back to the beginning. I was in my late 20s and had just broken up with a person who treated me really well, who I was all lined up to get engaged to, and was everything I thought I had wanted (had matched the list that I had made when I was younger to a tee).
The issue was that I kept getting intuitive messages that there was someone else out there for me, that I was moving in a different direction than him and that I needed to end this relationship, but I was terrified.
I eventually mustered up the courage to admit that while I couldn’t really explain why, I just knew deep in my gut and in my heart that we needed to break up.
This was one of the first times I ever took action on what my intuition was telling me, and it was scary and I second-guessed it a lot. However, my intuition had been so loud that I really couldn’t deny it, so I went through with it.
Immediately after we broke up, I started dating someone else. He had this amazing, flowing hair, owned a cool restaurant in the city, and was... a total hunk.
My friend dropped me off at his house one day and he came out wearing only basketball shorts, long flowing hair perfectly in place, holding a tiny golden lab puppy. She said: “are you living in a rom com right now? Who even is this guy?”
While this guy was definitely a hunk, his true colours started to show pretty quickly, and in the process, so did mine. I had him up on a pedestal, and in that space, allllll of my insecurities that had been dormant came out.
I basically felt like he was too hot and cool for me, and his air of elusiveness and him being so avoidant, which meant he was so hot and cold triggered all this anxiety in me.
Similar to in a rom-com where the conflict arises, those insecurities then fuelled a fire between us and we started to argue. Except in this case, he ended up also being unkind and crossed a line, and so that promptly ended.
From that experience, I had to learn that I had a zero tolerance policy for a guy I was dating being rude or unkind to me. That experience was such a big no to me that it helped me focus on my yes of a standard of having guys I’m dating always be kind and respectful.
I also was later grateful for that experience for giving me an opportunity to let some insecurities that needed to be healed be brought to the surface so I could work through them after that ended.
Lastly, that experience came at the perfect time. A classic rebound. I was so conflicted about breaking up with my ex that I really just needed to date someone immediately to help soften the blow. When this ended, I was finally ready to get my grounding again and finally start to process my feelings and what happened.
My Old High School Crush
A few months later, I met this guy who was from Toronto but lived in NYC when he was home for the holidays. Back in high school he had an air of coolness mixed with pretentiousness for whatever reason at the time I thought was crush-worthy.
So when he circle back one holiday season, I felt like I was living out high-school me’s crush, you know that feeling?
We had a fun “home for the holidays” romance, and then he went back to NYC. He didn’t ask me to come and visit. Instead, when I asked him about whether he would “be around when I visited my friends there soon” (*no trip planned - definitely planning a trip around him*) he thought it “could be fun.”
Know what happened that trip? He was really nice to me the first night we all met up, and then after that proceeded to ignore me the next day and the next night at a party we all went to.
The pain of rejection, and feeling foolish for having made this trip happen with the motive ultimately to see him, all stung.
I did what I did at the time and immediately went out and found the “next.” Interestingly, the guy who I met at a bar in NYC post-getting rejected by the other guy would end up weaving in and out of my love life for quite some time, but that’s another story for another day.
I decided that I wouldn’t do that again: plan a trip just for a guy and not be clear around my intentions.
My “no” was to ever plan a trip only for a guy and not be clear around that. My other “no” was having a guy ignore me was grounds for walking away. My “yes” was guys who actually pay attention to me when I’m in the room. My standards started fairly low, right?
Also, this was my first "seed" of what it might be like to date someone who lived in NYC, which is later exactly where I would find Chris.
Law School Cutie
Later that spring, I found myself dancing on the dancefloor at a wedding with a guy from law school I had never known very well.
He was so nice and as the two single people at the wedding, we ended up having the best time being each other’s dance partners.
The next day, he was flying back to Vancouver where he lived. Before he left, we met up for brunch and he asked if I would ever come to visit Vancouver.
“Well, actually… one of my best friends just moved there.”
While I had every intention of going to see her, I would conveniently push the trip to sooner so I could see things through with this law school cutie.
It was often me - pushing forward. Trying to make happen. Not always being clear of what I was doing.
And so how did you think that worked out?
For the next little while, he and I kept in touch. I made plans to go to Vancouver.
In between then and that Vancouver trip, he had a couple of short business trip to Toronto where we got to meet up only very briefly because he was working around the clock (I also had a pattern of dating men who were juniors in their careers and were worked to the bone).
Those times we did get together were really sweet though. I was excited, and really open to exploring the connection fully. We spoke all the time.
A month or two later, I arrived in Vancouver. We decided I would just stay with him because he was, once again, working almost all the time so in the fleeting moments he was around we could spend time together.
That week was really fun. I got to see him, see one of my best friends, and explore Vancouver.
Making myself coffee and journaling in his apartment after he left for work made me wonder what it might look like for us to be in a relationship together. Would I move to Vancouver? Would he transfer back to Toronto? Would we just be back and forth? You know how your mind likes to start to play out the story.
Until, I started to feel like the story wasn’t aligning with reality. He made a couple of comments about long distance relationships being the worst, and about him being so focused on his career at that point in his life.
I knew the avoidance red flags when I saw them, but tried to pretend I didn’t. The night that I started to feel that maybe this guy just wanted to have fun and wasn’t looking for a long distance girlfriend, I met up with another friend for dinner who also happened to be a wise therapist.
“Well, Catie. You can’t guess what he’s thinking, you’ll have to communicate about it.”
“Who me? Communicate about what? That’s so intense!”
“You need to get clear on what you want, and then you need to ask for that. You need to advocate for your needs.”
Advocate. That was something I could get behind. I was at the time a litigation lawyer, so my entire job was advocating, but for others. I needed to start to turn that same attention and advocacy toward my own interests.
That next day, he and I went out for dinner where I bought up with him that I wanted to keep seeing him and for us to try long distance. The long story short was: he didn’t want to do that. Too much work. Too many failed long distance relationships around him.
You know the drill. Except know what I did? I didn’t play it cool. I let myself be sad. I let myself be heartbroken. I let him see me sad and vulnerable, and I let him hug me and comfort me through that.
I let myself be vulnerable in a bigger way in that moment than I ever had in my years of keeping my emotions close to my chest with guys, and in that lesson about learning to advocate for my needs. And for that, I’m really grateful for him.
I learned to clearly ask for what I wanted through that experience, and it served me so well after that in discussions with guys who were looking for a relationship with me that I didn’t want, or when I was in a blurry situation where I assumed we were exclusive and wanted the same things but wasn’t sure.
I also made a pact then: no more flying to guys at all. No more trying too hard to make it happen.
A new “yes” to being clear and never being in a weird assumption around what we both wanted. A new “yes” to being an advocate for my news. A new “yes” to guys who were as kind as he was, even if we had been on different pages.
Fast forward to several years later, and 6 months before I met my big love and I was DM-ing with this guy on instagram. He lived in Austin, Texas and seemed so cool. He was a coach for men, had a podcast, and posted some really wise instagram captions.
I was crushing.
We chatted for a while on instagram, which then turned into phone calls and Facetimes, and eventually we came up with the idea for us to meet in person.
I was busy with work because I was tying up my law practice for good and about to leap into entrepreneurship full time, and so we decided that he should come visit Toronto.
This also worked with my new rule around not flying to guys. They could fly to me.
He had not yet gained much traction with his work, and so was bartending that Summer and trying to make ends meet. He kept saying he was going to book the flight, but he kept waiting to get paid.
Again, same mistake of being too keen and trying to make it happen, I offered one day: “why don’t I just pay for your flight, and then you can pay me back when you can.” This was also a very masculine energy move, the masculine being the providing, protecting energy, and the feminine being the receptive.
After the flight was booked, he changed his plans. He decided that he was done with Austin and wanted to move somewhere else, so was going to leave his apartment, pack up all of his things, and come to Toronto and then the plan was he would go to LA.
I was just about to leave my job, so if we got along, we discussed how maybe I could just come to LA too.
Since I decided to go with the flow and have no boundaries around my space or life, I said “Sure! Come stay with me!” So the plan was that he would come to Toronto and stay with me indefinitely.
This now makes me cringe so much to look back on, but I was in a different place, learning different lessons.
You have to understand that I am so excited about this guy. He is so different from anyone I’ve ever dated and at the time, this seems like a great and very refreshing thing.
For years, I had a “type” and I don’t think this was a bad thing (they were all very stable, very passionate about their career, but all worked in finance which didn’t really offer any flexibility). I often questioned how well that would work with the new life I was building that would include traveling a lot for retreats, and generally being location-free.
At the time, I was really craving freedom, and so I also questioned whether those who were in a traditional career trajectory were too stable or “boring” for me.
This guy was in the same coaching space as me, meditated, was into spirit and personal growth, and so was basically the complete opposite to who I had dated before. He was definitely a big personality, and certainly not boring.
I had often thought of how cool it would be to date another coach and for us to work alongside each other, so this guy matched what I thought I might want.
He arrives at my door and instantly I felt his energy was just… different than I thought it would be.
It wasn’t bad, but just, different.
It’s fun for the first 24 hours we are together because we have a lot to talk about. The issue is that about exactly after those first 24 hours we start to drive each other crazy.
While he had a great persona online, and offers a lot of wisdom on his podcast, it did not translate to the truth of who I experienced him to be, which was a shock. He was childish, rude, offensive, selfish, and calculating.
I won’t get into all the details, but about 72 hours after he arrived all of my friends were having basically an intervention with me saying this guy is the worst and you need to get him out of your apartment.
I was conflicted because in some ways I agreed with them, and in others ways I was resistant to believing the truth of what I was experiencing, didn't want to let go of the dream I had built up in my head and honestly couldn't even believe he was so different than I thought he would be, and I thought...but where would he go?
He would get a hotel. An Airbnb. A flight out. All of those things for some reason felt like such a hardship for him to endure if I communicated that this not going to work and he needed to leave immediately. Again, I cringe. But, alas, lessons I needed to learn.
After my friends intervention, and me coming to terms with this mess I had gotten myself into, I told him that he needed to leave. He was so mad, and said that he couldn’t because...he actually had only a little bit of money left and it was not enough to pay for more than a night or two at a hotel. So glad you packed up your life and everything in it with that type of cushion to support you.
Cool. Cool. Cool.
"Why can't I just crash here? I once stayed at these girls' place on their couch for like 3 months. They were so chill. What's wrong with you? You're really going to screw me over here."
I called a friend of mine who is older and wiser and is also a coach who has helped me so much in many difficult situations because I didn’t know what to do.
“Catie, your job is not to save this guy. This is his own hero’s journey, he’ll have to deal with his own consequences, and it’s not your responsibility.”
Ahh yes, not my problem. Yet so easy to make it mine.
I took some time and space to figure out what to do next. I went to yoga and a walk in the park to gain clarity.
Even though things hadn’t worked out, we had developed a friendship over the last 4 months and I felt bad kicking him out before he had a plan on where he was going next and how he was going to get there.
I didn't feel unsafe in any way, I was just now having to deal with a disaster that I needed to remedy.
So I tuned in with my own truth in meditation and came up with an agreement: he had 10 more days to stay. I was in my final 10 days of working my law practice and was really busy tying up loose ends. I was barely at my apartment anyway, so he could stay and get his plan together for where he was going next, could figure out borrowing or getting the money he needed to get there, and by the time I finished up at work on my last day, he would be gone.
I call him now the iceberg because there was so much boldness and interesting facets to explore above the surface, but then once you got below the surface it was a whole lot of NOT GOOD.
This experience was probably my worst. Again, I’ll spare all the details, but it also included him eating all my food, trying to go on Bumble dates while he was staying there, and not even saying thank you before he left.
And yet, I’m grateful for that experience now. This was the biggest NO experience I had ever had, and it paved the way for the ultimate pivot toward what was going to be YES for me again. Eight months later I met Chris.
I have to give credit to that same wise coach because she said: “maybe this experience has been showing you the extreme opposite of what you don’t want so you can be so clear on what it is that you do want. And maybe now you’re seeing why there’s a reason why you’ve dated guys who are similar to you in terms of your groundedness, and how this guy being so different from all of them maybe wasn’t a good thing. Maybe you’ll see that even if a guy doesn’t want to meditate or go to personal growth seminars, that he instead accesses clarity on a long run, and grows through how he handles challenges at work. Maybe you’ll see that you actually really appreciate guys you previously tended to date who were really dedicated to their careers because it shows their commitment to things in all areas of their lives. Maybe now you’ll have a new lens when you’re seeing others that you’ve been writing off for the last while.”
After that experience, I had a long list of what was a no, and also a reconnection with wanting some of the qualities of guys I had once dated before that I now appreciated on a deeper level.
I realized that I didn’t need someone to be as into meditation and spirituality in the same way I was, because you can be into all of those things and still not “practice the practice.” Meaning, you can say you meditate but still be rude and judgmental. Instead, I needed someone who was open-minded, led from their heart, and lived in integrity.
I also needed to take a long look in the mirror after that experience. Why did I have no boundaries? Why did I blindly let this guy into my life? Why...why...why. A lot of good questions and tough questions I needed to sit with.
The main thing was, I was about to leave a career that had defined my identity for the last 9 years. I was really torn up about it, and even though I was so excited to coach full-time, I was deeply grieving my lawyer life.
To make it more difficult, my family was not supportive of this career change and was vocal about that, and most people thought I was nuts to be doing what I was doing except for a few trusted friends. And in addition to that, a bunch of my friends were getting married, engaged, and settling down that Summer, and I felt like I was on such a different path.
I was struggling with how to process all of that at once, and so I have compassion for myself for holding onto the glimmer of light of the potential of this guy, who before we met in person, was so hilarious and fun.
So I also needed to learn about having compassion for myself for making decisions I wouldn’t now because I was in a different place, and awareness around what I do or don’t do when I’m struggling through a hard transition or time.
I wish I had just admitted that I was struggling, but because I needed to be so confident in my decision to leave my job and let go of that identity, I didn't let myself.
Instead, I let this romance be a distraction, and ultimately everything that was swept under the rug blew up in my face.
After the Iceberg, I was done with the lessons. I was so over it, and so ready to meet my person.
I said "Universe, enough. Guide me to exactly what I need to do, heal, shift, and work through in order to call in my One."
And you know what happened? It did. Right away.
And those lessons and experiences became the four months of my life before I met Chris. It was a process. A journey.
And that journey, and those lessons, experiences, learnings and teachings became the content of the Big Love Course, a course that has now helped lots of other women call in their big loves, and also clear their hearts, their mindsets, and regain their confidence back to goddess-queen-levels too.
Lessons in love are not always easy, which is why I think that true love is not for the faint of heart.
I don't regret any of these experiences, and instead cherish them, because they were all the things that brought me to this moment, snuggled up in bed, writing this with my soulmate next to me. Waiting for the snowfall to end so we can get out skiing, an activity I once loved but had stopped doing, and was only inspired to reconnect with because of Chris.
Trust the journey that your on. Trust the lessons, the setbacks, and the downfalls.
They're all helping shine you, strengthen you, and help you get to the place where you need to be.
After this experience with the Iceberg, I began the journey that now is the Big Love Course. It changed me, changed my heart, my life, and helped me to heal the past so I could call in my One.
I would so love for you to join.