“Oh my god, I’m so flattered,” she said.
“But I have a boyfriend.”
My brain broke, then.
It was one of those paradigm-shifting moments when I’d finally realized that asking somebody out wasn’t a death sentence.
Or, even better: when I asked the cute barista out at a local coffee shop that I frequent, she said the same thing but instead, “I have a girlfriend!”
I thought that was charming in its own way.
You find out so much about people when you ask them out!
What my nervous system had been convincing me up until that point was that if I asked anyone out that they would murder me.
Like, in the case of my Lyft driver, she would literally whip out a butterfly knife, climb into the back seat of the car and carve my face off and wear it as her own.
That’s how our brain, historically, has protected us from predators.
I quickly realized that this deathly terrifying fear of asking women out in uncomfortable situations won’t ever kill me.
For decades, I’ve had so much anxiety wrapped up in the fact that I’ve always wanted people to feel okay to comfortable and not like I’m trying to have sex with them around me that I’ve completely avoided all forms of contact with women (and otherwise).
And then, suddenly, something broke.
I never felt the same again.
Your only job in life is to prove yourself right.
The most, fuck yes, fuck everyone else, I’ve ever felt was when I’d convinced about seven colleagues who I’d known for maybe a few months at most (and a few weeks in the least) to part ways with about $300 of their hard-earned money for a mastermind program that I was going to be running for entrepreneurs.
Asking them for that much money felt like the scariest thing in the world at the time.
I’d invited them to a loud bar to make my pitch and offered to pay for their first drink to hear me out.
It felt like a bribe in some ways but sometimes you need to bribe people to convince them to talk to you and I think that’s okay, too.
I was so nervous that my ass started to cling to the seat from all of the sweat that was dribbling down my crack.
At the end of my “pitch” — which, I label it a pitch because anytime you’re asking for money, it’s a “pitch” but really it was just a conversation with a proposition at the end — all of them agreed to be part of the program.
It felt like one of those earth-shattering, mind-altering moments in life that you don’t get to experience frequently enough.
Like all of the “that won’t work” comments, I dealt with and people telling me what I was working on was derivative dog-shit and total nonsense just dissipated.
Like all of my friends who believed that striking it out on my own was ill-advised and that I should just get a normal job were finally wrong.
I had been trying to prove myself to the wrong people, though.
I felt like I was on drugs and having an out-of-body experience.
Maybe the alcohol was kicking in quicker than I’d realized.
I was dressed to the nines in my fanciest (and only) dress shoes, loud European chino pants, and a fancy suit jacket splayed out in the middle of the way too fancy resort’s lounge area just beside the main bar.
I was drinking a drink that matched my attire but certainly not my income level or anything particularly celebratory.
And I was just watching the people walk by, sipping my drink and getting closer and closer towards intoxication.
I reminded myself that I could, in theory, live like this every day if I wanted to.
Large, you know?
That if I wanted to live that sorta life, the only thing ever preventing me from doing so was just myself and all of the short-sighted things I’d been telling myself like the fact that I can’t afford that.
Like, that, “I can’t walk up to a beautiful girl in the corner of the bar and ask her out.”
Because she’ll say no.
Or, because I’m not good enough.
Or, because she’s married.
So what?! I began to realize.
I felt my reality slowly start to slip away.
I don’t know if you’ve ever had one of those moments when you realize that some of the thoughts that you regularly have on a day-to-day basis are stupid, but I certainly did.
If I wanted to, I could slave away at a trading desk for 22 hours a day and hate my work-life but then have enough money to squirrel away on absurd table-service, the most expensive restaurants in the world and exotic vacations as often as I’d like.
That I could, in theory, develop healthy relationships with multiple women at the same time and create some sorta revolving door of sex that just swirls in and out of my luxury highrise apartment.
Like in entrepreneurship, especially, the only thing that’s stopping me just short of building the things I want to build is some arbitrary bullshit.
And then the world split in two.
I started to feel like, in some other alternative reality that there was another me who was already doing all of these things.
And that if I could just find a way to better connect with that individual that I would get everything I’d ever wanted.
But then the enjoyment that’s so often derived from that chase would dissipate.
And everything that I’ve ever found luxurious or new or particularly noteworthy wouldn’t be anymore.
And I’ve never wanted that.
Maybe I’d been right all along.