February, 2017
That’s when my last relationship ended. It didn’t officially end until the spring, but I was going through some things that made it tough for me to be in the right head-space for a relationship. In January, I was fired from a career I had put my everything into. A month later, I went snowboarding for the first time that season and ended up breaking my arm badly. At that point, I wasn’t a boyfriend in any meaningful way.. I had too much that I needed to figure out. Bless her heart, she was awesome and supportive the whole way through. Probably the most amicable breakup I’ve ever had.
May, 2017
One of the relationships I kept reflecting on last year was with Max. We had dated a couple years prior. There was so much chemistry between us and so much that we had in common. It seemed to work on every level. Except she was bugging to go explore the world and I was committed to my career. I was also too dominant in that relationship, more controlling than I would’ve liked to be. There were times where her free-spirited nature was at odds with my career goals and I would try to convince her that my career goals were a higher priority than her being herself at all times. I wish I hadn’t.
In understanding why I had been fired, I realized that it was a matter of fit. In trying to understand where I would fit best, I realized that I needed to do a better job of understanding myself. That journey mirrored so much of what Max had learned leaving a big 4 accounting firm and working for a start-up. I wish I had done a better job of understanding that story. She helped inspire a lot of growth on my part, and I thought she might appreciate knowing that.
December 2017
I wrote a blog post about her. Flushed out every thought and emotion I had on the subject and realized a lot of things I still hadn’t considered. It was a good experience. At the end, I figured I would tell her about the ground that I had covered and thank her for her part in all of this. I made a YouTube video and send it to her on Christmas. I was clear that I wasn’t looking to get back together, but I’d be lying if I said a part of me wasn’t trying to plant a seed for the future.
January 2018
After about month of radio silence, she emailed. She said some nice things and asked if I was up for a video call. I said sure – and then proceeded to hear nothing from her for another month. I knew she probably had a full plate so I eventually just emailed, “whats on your mind?” Her reply was more direct this time. Said she was busy, was happy for me, then questioned much of what I had said, and seemed to have forgotten about that video call. I replied, tried to explain, but then said it would probably be easier over the phone. No reply.
March 2018
Another month of radio silence. All I wanted to do was let her know what I had gone through, and hoped that she would be happy for me. Maybe I should send her a link to the blog post about her? At least it would be the full story. So I messaged her on WhatsApp but before the opportunity presented itself, it became a conversation. She began to question who I had ‘become’, suggesting that I was still the same person. It was tough trying to explain how and why over text. But I tried. At one point, she even ceded that it seemed like I was a whole new person. Maybe she was just saying that hoping I would stop trying to argue my point. Regardless, it was clear she lacked the motivation to invest the time into understanding that person.. and everything that I had felt towards her had shifted. One of the things I appreciated about her most was that understanding me seemed effortless. Now, not only was there effort involved, but she had no interest in putting the effort in. A bummer at first, but it felt good to have clarity.
Right around that time, I was trying to go on a date with a girl named Mia. Someone I dated for a bit a few years ago, and someone who I had a bunch of fun, nerdy stuff in common with. She’s all kinds of cool, but she’s also working through some things. When things get difficult or confusing, she hides. She tried that with me before and I just walked away.. it’s why we stopped dating the last time. This time, I was more interested in helping her rise above that. So we tried to go on a date, but then she got busy. We rescheduled, but then she got busy again. I told her I knew this pattern, and I was happy to walk away if she wanted me to, but she didn’t – she was struggling with old habits.
April 2018
So we tried again, but work. And again, but work. I was on my way out this time, but did so with a link to a post I had written about her, so she would at least know what my honest feelings towards her were. She was surprised. She opened up to me more than she ever had, and seemed that much more motivated to see me. Seemed like progress. So we rescheduled.. and she ghosted again. This time, it was because she had read the rest of my blog and found out about Max. She was afraid that I was using her to fill a Max-shaped void. I couldn’t hold it against her, it was a legitimate question that I also had to ask myself. We talked it through, and agreed that we would make attempt number 6.
Had I been stood up 6 times with no difference in the context, I’d be worried about my mental health.. but that wasn’t the case. With each time, progress was being made. And I could tell that these were big steps for someone who didn’t have a lot of opportunities to take these steps. Unfortunately, it was also creating an imbalance in the relationship which I knew was unhealthy. She pleaded that work was being unfair, and that she wasn’t leading me on, and how interested she was… but she couldn’t get her actions to match her texts. The outcome was disappointing, but I’m happy that I treated the situation with compassion and understanding instead of walking away at the first sign of getting hurt.
April 25th, 2018
The very next day, Max texts me. Said she’s in-town, and would ‘love’ to get together. Well then. We book a late dinner for Sunday. She also wants to smoke a joint together, so we plan to get together later in the week too. Easy way to get my mind off Mia, I guess.
April 27th, 2018
Arrive to a 3-day self-help seminar on Friday. Pretty skeptical about what I’m walking into, but doing it with an open mind and the best of intentions. A girl catches my eye. Was partnered up with her at the end of the day for an exercise where we’re asked to sit directly across from each other and tell a victim story while looking into each others eyes. We spend most of that time looking at each other and cracking up, because neither one of us is any good at pretending to be a victim. A fun introduction. We shall call her.. Lulu.
On the way home, I text my buddy who invited me to the seminar, letting him know how it went. He asks if I met anyone interesting. I say everyone’s interesting if you ask the right questions (holding back from saying I met this really cute girl). He tells me that he has another friend who’s there doing the seminar and he hopes that we have a chance to meet.. and that her name is Lulu. As he puts it, we’re two of his closest friends and the ones he goes to for good conversation. Wow.. that’s kinda cool. I ask if he’s interested in her, or if she’s in a relationship. Says he dated her for a bit way back, and he thinks she’s in a relationship with someone. Well, never mind then…
April 28th, 2018
Saturday’s part of the seminar put me and Lelu back in close proximity. I do my best to avoid creating interactions, but don’t avoid them either. Our chemistry continues to build. I text my buddy again that night, asking if he’s sure that she’s in a relationship. He says yes. I tell him that while my instincts around these things are a bit rusty, pretty sure this girl is into me. He tells me a bit more about her and shows some enthusiasm around us connecting beyond this seminar.
April 29th, 2018
Lulu was definitely the best part of my Sunday seminar. We sat beside each other a few times and ended up doing a couple of the 1 on 1 sessions together too. I eventually asked if she knew we had both been invited by the same friend – she didn’t. She was excited, especially because it meant that there was a good chance we’d see each other again. As the day went by, everything suggested more chemistry and more interest. At the end of Sunday’s seminar, we were supposed to thank people who we had connected with and tell them what we appreciated about them. She approached me and opened with “Thanks for being the best looking guy here, it gave me something to look at”, and followed with a few very thoughtful compliments. I replied, telling her that she was the highlight of my weekend and that I hope to see her again.
Now to go directly from that self-help seminar to dinner with Max. Along the way, I text my buddy and ask if he’s sure that Lelu is in a relationship because everything that happened that day would suggest otherwise. He ended up taking her out for dinner and dug in. Said she’s only been dating this guy a short while, but she doesn’t see it going anywhere. Tells me not to worry, and he’ll connect the two of us before long. I have no interest in being the guy that breaks up a healthy relationship, but if she’s already on her way out.. I can’t help but want to see her again.
So I arrive at dinner with Max – fancy sushi. She gives me a big smile and a big, but not too big of a hug. We get seated and start talking. Eventually, she asks me about my aspirations. I think I say something like creating the most significant positive impact I’m capable of. She says that’s a bit vague and asks what the most significant positive impact I think I’m capable of. I may have told her President of Mars. She called bullshit. That probably needed a little more explaining.
I guess for starters, I really do think that the upper-limit of the human mind is often well beyond the limits we place on ourselves. Mars though? I told her that the bigger the problem, the more motivated I am to solve it and I can’t help but want to find solutions to the big problems we as a species are facing today. Ok, but why Mars? Well, I’ve seen well-intentioned people come and go, only for their ideas to fall on the deaf ears of a system which is designed to protect itself from change. I often think that what the world desperately needs today, is a blank canvas where a new government could be established with modern policies. If we only had the opportunity to lead by example, how quick would the world be to adopt those good ideas? Unless I’m missing something, Mars will most likely be our first opportunity to build something from scratch.
I think she made an attempt here to bring me back to reality and asked me to connect that to a real goal. I told her that while I have these ideas, and they seem logical in my mind, I still need to prove that they can exist outside my head. I need to take my personal philosophies, my ideas, and my ability to execute, and make something special. If I could make something special, that something that people can understand as an expression of my mind and my vision, people would notice. If people noticed, they might appreciate, and if people appreciated, they might just be willing to hear what I have to say. While that something special can take on different shapes and forms, no form comes more naturally to me than building a business. So I told her I was working on building a billion dollar company.
She said back up the “B”. What? Back up the “B” in billion. What do you mean? She asked if I knew how hard it was to build a billion dollar company or how rare they were. She didn’t take kindly to what she thought were grandiose exaggerations of what I was really up to. She knew that I was working for a cannabis retail start-up, but I don’t think she understood the potential behind it. I told her about the awards, and the industry growth, how visible our founders were, and how ahead of the curve we were. She didn’t seem to care. I said that if you had to pick an early winner in cannabis retail, it would probably be us, and to say that wasn’t an opportunity to build a billion dollar company was untrue. She still didn’t believe me. Or maybe she didn’t believe that I would do it.
I did my best to ask her about what she was up to throughout the evening. She sounded like she was dealing with a lot, but persisted that she was happy. She certainly valued all that she had gone through in the last year. I asked her what her goals were and she said to land a job this fall. It looked like she was lined up for a fancy title at a mid-sized private equity firm doing some level of analytics. I asked if she had any big goals. She seemed less sure about this… maybe something to the effect of using big data in driving HR policy, limiting inequality in the work place. Sounds neat.
Despite all my efforts to guide things in a positive direction, we kept finding our way back to my aspirations, and her lack of confidence in my ability to accomplish them. I wish I had been able to tell the story of how I got from being fired to wanting to set up camp on Mars.. pretty sure things would’ve made more sense that way.
The night largely seemed like an exercise in her trying to cut me down. I was used to her being an optimist, a big thinker, open-minded, and supportive. Now I wonder if it’s her that’s changed or if it was just my memory of her. I was all but convinced that who I had become was a better fit for who she was. But as soon as I realized that, I also knew that who I had become, might not be a fit to who she is today. I think that’s what I was facing. Somewhere between her big corporate gig in silicon valley and her MBA, her mindset seems to have changed. Where she was once about possibilities, she was now about limitations. There’s probably also an element of trying to stick it to your ex-boyfriend… and I probably deserved it.
At one point, I said, “This is unexpected, you’re usually more..” I cut myself off, and apologized, saying that it wasn’t my place to say something like that. It threw her off, she knew what I was getting at.
It was getting late, we asked for the bill. We hugged again outside and she apologized for being less supportive than she used to be be. We said goodbye.
April 30th, 2018
Knowing that we had made pseudo plans to hang out later in the week, I sent her a text. I basically thanked her for dinner (she insisted on paying), then thanked her for challenging my goals. I said that I’m steadfast in dreaming big, working relentlessly towards those goals, and being at peace with where that takes me (I’m all about shooting for the stars and landing on the moon). I said I’m rarely challenged on these things and if nothing else, it was good exercise. I also said that based on our conversation, I had the impression that there were probably other people in town she’d rather spend time with and that if I was right, it was all good with me. No response.
The day before she left, I sent a text saying I hope I didn’t upset her with what I had said. I told her I was happy for her, and wished her the best of luck. She responded back saying she had been busy and yes, lots of people to see.
May 1st, 2018
Speaking of radio silence, Mia messages me the next day. Apologizes for the incoming wall of text, and the proceeds to say some very nice things. She talks about how strongly she feels about the potential between her and I. Then talks about her struggles and the progress she’s made. Then she talks about her feelings. Then she says something to the effect of, ‘and I won’t hold it against you if you never want to talk to me again’.
I agreed with a lot of the things she said about the potential between her and I, and I appreciated that she recognized and appreciated the progress she had made. So we get into a text conversation where I thank her for opening up to me and we get into the possibility of trying one more time. I ask her what the difference this time would be, and she says a strong effort. I ask if that means that the last 6 times weren’t strong efforts. She says that this time, she’s just going to go for it – be less cerebral about it. I told her it didn’t sound all that convincing. She reminded me that she wasn’t very good at explaining this stuff over text. The conversation kinda fizzled after that.
Went to bed, had a dream that she had made an effort the following day to make something happen between us and I was happy about it. Woke up to no such effort. Decided that I was being unfair. Told her that if she wanted to explain things to me in person, I would make the time for that. My ask was that it was on the weekend and at my office (so if she pulled a no-show, that I could just keep working). She was receptive. She planned to come by on Saturday but on Friday she asked if she could move it to Sunday. This looked familiar. She didn’t come by on Saturday or even get back to me about Sunday. And that was the last I heard from her.
May, 2018
A friend of mine cracked a joke a couple months ago saying that I should jump on Tinder with a bio that says something to the effect of, ‘Dating is confusing, anyone wanna blaze and hang out?’ Dude is sounding like a genius right about now.
Ironically, back in April, I was talking with a couple female friends about the challenges of dating and I suggested this was why dating apps had become so popular. One friend was in her 50s and had been married for 27 years so she had zero interest Tinder. She said that people need to get outside and engage each other in real life. I asked where that might be appropriate these days given all the tension between men and women. Every answer she gave was immediately turned down by my 20-something friend. At the gym? Nope, don’t be gross, I’m just here to work out. At a book store? Just because I’m here buying books doesn’t mean I wanna be hit on. In-line at a cafe? Nope. I told them I found it all very confusing and hoped they would find some empathy for the other men out there feeling the same way.
Only a few weeks ago, my sister and sister-in-law were in town. I asked them about the dating scene and the tension between men and women. I get that some men are shitty people. I’ve even lost friendships over that kinda stuff. But this general negativity towards men seemed unhealthy. They responded with an analogy which they were quite eager to share: Think about men like a bowl full of skittles. One of them is poison, but you don’t know which one. Why would you risk it? It wasn’t the right time to tell them that they’re using the same logic as those who avoid Muslims in fear of Muslim extremists.
My mind is searching for a connection between all these interactions. Considering the rise of neo-feminism and the #metoo movement. Considering the impact of social media. Considering the heightened levels of anxiety, stress, and drug use. I’m trying to see through it and to the other side… and I can’t. I’m not saying we won’t get through it. I would bet that we do. I just don’t yet see how. I think this gets worse before it gets better and that concerns me.
Some men have learned the advantages of identifying themselves as an ‘ally’. Some have learned that you can improve your odds by dating multiple women at the same time. Some have learned that it’s easier to get turned down if you turn into a giant asshole afterwards. There’s even a sub-culture of men who are downright confused and losing hope of ever figuring it out. Everyone’s dealing with it in their own way… but none of these are about how we make it better.
This is a big problem, and I have a swell of motivation to find a solution for everyone out there that’s struggling to find meaningful connections. I think much of the solution is based in honesty and real communication. Not just honesty with others, but honesty with ourselves as well. We’ve also romanced the concept of love since we could first tell stories, and it’s warped our expectations of what it is, where to find it, and how long it lasts. If we would only make the effort to understand ourselves and then to understand one another, I can’t help but think that things would get better. To get there, perhaps we need to be reminded of why we should be courageous when facing those we fear. Or why we should be compassionate towards those who have hurt us.
… or sex robots for everyone?
My Mental Model 