How to break a girl's heart

how to break a girl's heart.jpg

Whatup, boo? It's been a minute, huh?

Well I hope your year has been off to a better start than mine, because I started mine by breaking a girl's heart.

She reached out to me after I became semi-Internet famous because of a YouTube video, as did a few other girls – but her message stood out. She seemed to have one of the things that I am really looking for in my partner – thoughtfulness. And she seemed really cute! I couldn't help myself, and I even deleted all of my dating apps within a few weeks of our first date, I mean video chat.

Oh yeah, I forgot to mention – she lives in Toronto, we only spent about 48 hours together in person, and we had about a 6 month long relationship.

Watch/listen to this blog post

I know, I know…save your judgment – I have enough for myself 😆

It gets even worse though, because I had already bought tickets to go see her again, but I just. couldn't. go through with it.

Which was a real bummer, and not only because those flights were nonrefundable, but because we are BOTH super kinky, in similar ways 😉 and I knew, that if I went to see her again, we would explore each other in all those intimate ways. It was certain.

But, I just wasn't feeling fulfilled in the relationship. I think I knew this subconsciously, because I would oscillate back and forth, going from being madly in love with her, to finding flaws in everything that she did.

And actually, I had already broken up with her, once before, at the end of my one and only trip out to Toronto. And I had even told her (literally quoting myself here) "I'm going to want to change my mind, but this is my final decision." I knew I was weak, and that I would miss her. I still do.

Anyway, a few weeks after I broke up with her, I wrote her a horrendously personal, 7,839 word email (phew) explaining myself and what I'm looking for in a partner.

7,839 words. That's like 10 fucking pages in Microsoft Word – single spaced!

Here's proof that I'm insane.

Word count

And? What happened?

Well…it worked! We were back to dating again shortly thereafter.

I know…I know…even I am rolling my eyes at myself, for getting caught up in the Hollywood "grand gesture" methodology. You know what? It felt like the right thing to do in the moment, even if it makes me cringe when I look at it now 😬


Why the hell did I do all of this?

It's a good question, and one that has been gnawing away at me ever since I ended it for good, which was almost 2 months ago.

And here's what I've gathered –

For the majority of my life, I have had ZERO choice in women. And now there was this cute girl who liked me, who was really sweet and caring and loved to talk to me, and who wanted to have wild, kinky sex with me!

I mean, COME ON guys…who the hell am I to be picky? Isn't that like every guy's dream girl??

Well, sort of

Outside of our sexual chemistry, I felt…bored. She didn't challenge me, she didn't inspire me, and she didn't push me to be the best version of myself.

And that sucked! Because there were a lot of things I really liked about her. She was very emotionally mature (which is great, because as you probably know by now, I'm basically a child) she was an incredibly thoughtful listener (which unfortunately, is such a rare trait to come across) AND she had a fantastic vocabulary (which is a huge turn on for me).

And OH MY GOD, the sexual chemistry! I told you about that, right? Yeah, I definitely told you about that…

Ok…anyway… (now you see why I say I am a child)

ANYWAY, it didn't matter…because I just couldn't help but feel that she was...too nice. Like I could literally do ANYTHING, and she would be okay with it. I could just be a vegetable on the couch, and she would still love me for it.

And you know, that certainly sounds exceptionally loving, and I do want my future partner to be there for me, even when I'm not at my best, but I don't want her to let me slide by without working to be my best every day. That feels like a huge disservice to who I am, and what I stand for.

– –

So even though I knew, in my gut, that she wasn't the right one for me, I thought about just going through with my plans, to fly to Toronto and her again. I thought we could just "have some fun," and then I would come back to Seattle, and let her know that I wasn't feeling it. I mean, technically there was no committed relationship – we were just getting to know each other.

But I couldn't. I just don't have it in me to crush someone in that way.

The fact that it even got this far still weighs on me, and I haven't talked to her in over 2 months. I feel like I was saying and doing all the right things with her, because I knew they were the right things to do – not because I actually felt like doing them.

And that scares me – that I've become capable of that. Is that what this whole journey was for? To end up leading someone on, in that way?

– –

I really did hurt this girl, and I'm not proud of it. Despite her not being right for me, she is a tremendously caring, generous, and loving person. Never have I ever felt so accepted, and cared for. When I went to visit her, she took on the role of my assistant/caregiver, helping me to do things like use the bathroom, take a shower, and even get dressed.

And that is an incredibly personal thing for me, as it typically takes me a long time to trust someone enough to even ask them to care for me in that way. But, I never had an ounce of hesitation with her. I just knew, that it wouldn't be an issue. Because she's just that kind of person.

So again…who the hell am I to be picky? Isn't that level of caring something that is so rare, so benevolent, so…loving?

I wonder if I will ever find something like that again.

Or why the hell I would even want to give it up? Especially after my previous girlfriend would say things to me like "sometimes I just wish you could pick me up and throw me up against the wall," and after several women have explained to me, very bluntly (because I have asked them to) that they do not want to date me, because they can't see themselves caring for a partner in that way.

So it started to feel like I'm just not going to be able to find my girl. Because either I won't be satisfied with her, or she won't be satisfied with me. So I thought, "maybe I should just enjoy this, maybe I should just learn to accept her, because this is as good as this going to get."

– –

But I couldn't. I told myself that by saying no to this girl, I was saying yes to what I actually do want. That by ending it sooner rather than later, even though it hurt to my core, I was shortening the time that it would take to find the girl who is a good fit for me.

But I wonder…do I even know what that is?

They say "you should know," right?

"You should know what you're looking for, so you know when you've found it."

And I thought I did know.

1. Exceptionally witty.

2. Deeply thoughtful.

3. Delightfully feminine.

But does any of that stuff really fucking matter?

Shouldn't you just want to be accepted for who you are? Isn't that enough? And what right do I have to ask for more?

– –

I don't know the answer to these questions, and that has caused me to question a lot more in my life. What do I want in my life? Why do I want those things? Why did I start this blog? Am I just trying to fill some void? To make up for some insecurity? Why am I so judgmental? Am I really just not okay with who I am?

And why am I so hell bent on finding a partner? Maybe I should just learn to be okay on my own? Maybe I'm trying so hard to be seen as "normal." Maybe I'm so angry with the world, because I feel so different, and all I want to do is just FINALLY fit in. Maybe that's why I have become this judgmental, picky, arrogant person that I am. Maybe these are the reasons why I work so hard, and I'm not able to tolerate deficiencies in other people. Because I'm just not happy with myself.

But I can't say that this life, or this path that I have chosen, hasn't served me well. I've accomplished a lot, I've secured myself financially, and I've even built great relationships with my friends and family. But maybe there's some more growing I need to do.

– –

As the feelings of loneliness have skyrocketed in the past two months (because I haven't dated) I still keep wondering, if maybe I should've just gone and enjoyed the time with her. Why didn't I just go, and at least have some fun, crazy sex with her?

But I'm glad I listened to my heart (and to a close friend, thank you Irene) which told me that I'm looking for more than just the crazy sex stories. Those stories are just…not enough. A lot of dating coaches tout them, as if they are the ultimate goal. And even I thought they were, for a while.

But even though this girl was into all the same, twisted, kinky things I'm into, the sex was just…not that great. And I think it's because we didn't have that deep, intellectual connection. I didn't feel like she had that same sense of drive that I do – that drive that causes me to wake up most days ready to attack the world.

I have had, that special connection, once before, with a woman who was equally driven, and the sex was earth shattering. Like seriously – hands down BEST sex I've ever had. And, it was just plain old vanilla sex.

This woman, was, twice my age…and I was honestly inspired just to be around her. I loved talking to her, because – she didn't just accept what I said. She challenged me, she spoke her mind, and she even pushed me to learn things which she believed were important for me to know. I have her to thank, for teaching me to invest in my retirement from a young age.

And I wish more women were like her – especially in being super sassy, in making guys work for it! I ALWAYS had to work for it with this older woman – when I would text her something kind of raunchy, instead of witty, she would flat out tell me, that I could do better, and I LOVED it! I would spend all my spare moments thinking about clever comebacks to her quips. It was like a never ending game of verbal sparring, with me as the pursuer, and her as the chooser. She was exceptionally confident in her worth, in what she brought to the table – and when she chose me, I felt like a king.

And she did not compromise on her values – oh no. I once texted her that I was outside her place, to pick her up, and she teased back, with something about how a gentleman would come to the door. She didn't care that it was raining, or that I am in a wheelchair. She knew her standards, and she let me know of them. And it wasn't in a fussy, "you-must-do-this" kind of way – it was still my decision, but I wanted to rise to the occasion. From then on, I always met her at her door (even though it had steps, so sometimes I would be out in the rain for a minute until she came out) and I felt like more of a man because of it.

But with the girl from Toronto, there was very little of that. There was a lot more of her just laughing at my jokes, and sending sweet, gentle, caring text messages back. And those are nice, if they happen occasionally, but they just get boring if they happen all the time. There was no challenge.

And so I just didn't feel that this girl was capable of taking on the world with me. In my gut, I didn't see her as a strong addition to my team. And that's ultimately what I'm looking for – someone who wants to crush it, together. Someone who wants to conquer the world together.

I think we all have a certain desire within us, to step up to the plate, to feel that our partner is a catch, because we have to be our best selves to keep up with them. I know I certainly do.

And because I wasn't feeling that, I knew I had to end it.

– –

Even though, for some time, I did truly believe that this girl was the one. I thought I had finally found her.

But I didn't want her. I wanted the woman who she had the potential to become. Because I would tell her to tease me more, to not be so nice, and to say no once in a while. I was trying to mold her, into who I thought she had the potential to be.

But you can't date potential, because then you are waking up every day, hoping that your partner is someone else. And that's just not fair to either of you.

– –

And maybe I will never be happy, because I'm looking for perfection, which doesn't exist.

But every person who I have talked to, who is in a successful relationship, has told me that they didn't feel that they found perfection, but they also certainly didn't feel that they were settling. And I don't want to settle! I want to be with someone who keeps up that witty banter, who has goals that she is aggressively pursuing, and who wants to conquer the world together.

– –

So…what's the lesson here?

The lesson is – don't try to change people. It doesn't matter if you wish you could accept someone, or if you think you might someday accept them – those thoughts are delusional. If you cannot accept someone today, you won't be able to accept them tomorrow.

I have now been on both ends of this – my ex-girlfriend couldn't accept me, and I couldn't accept this girl. Believe me, it is SO much better for the both of you, to end it sooner and let the healing happen.

And that sucks, because that tenderness, that closeness, that person to tell about your day is SO intoxicating. Hell, when I broke up with this girl in Toronto, I cried on her shoulder, and it was the BEST feeling in the world, because we were SO close, and she is SO loving, and she is the only one who could truly understand me in that moment.

And I wanted so bad, to do that for her, when I finally ended it, for good, but unfortunately, that's not my wound to heal. I knew that the sooner I ended our communication, the sooner she would be able to heal. So I didn't reply, when she said that she didn't even want to be friends. because that decision is her right, and there was nothing I could say that would make it any better. Given the way I handled things, I don't blame her for not wanting any contact with me. I should've known myself better, and because I didn't, I don't get to keep this great person in my life. 

I also thought – the sooner she hates me, the sooner she can recover.

But something tells me she doesn't hold hate for me in her heart. Because again, she's just not that kind of person.

And so I wonder, if I'm making, or have already made, the biggest mistake of my life. Because it's not every day that you encounter someone like that.

So I had to step away from my blog – because I wondered, who the hell am I, to tell to find love, when I don't even know myself, and I ended up hurting someone in my pathetic attempt.

– –

The reality is that I don't know. I don't know how to find and sustain a loving partnership. I don't even know if I know how to do it in friendship.

I do know that I'm quite afraid of failure. I do know that I've had a life of privilege, and that I've become a very judgmental person probably because of it. I do know that I have this weird idea that once I get the girl, my life will be magically better, and that I will be "done," so to speak.

But I'm tired of that. I'm tired of hoping that someday a girl will accept me. I'm tired of worrying that a girl will see something I created, and then be turned off by it. So I'm just going to create what I want to create, and share myself with you. I'm going to try a bunch of stuff – and honestly, some of it won't even fall under "dating advice", and I might fall on my face, but I will learn from it. And I will be more open and honest with you, as I have been in this post, when it feels right to me.

So stay tuned, because it might not all be pretty, but I certainly hope you'll join me for the ride :)

Amin Lakhani
The Dating Coach on Wheels

Amin Lakhani