When I was a senior in high school, I asked Helene Horan to prom. She said yes. Looking back, I really wish she’d said no. In fairness to her she got there eventually.
I didn’t know Helene that well, really. We’d been in school together for years. I think we first met in a middle school gym class. That fall we’d run on the cross country together. She was pretty, and athletic and seemed cool.
Those weren’t in of themselves the criteria I used to decide to ask her. More than anything, I thought that having her as a prom date would confer me some status. In a thought process not unfamiliar to many high school boys, I figured that having a pretty, athletic, cool prom date would mean people would view me more favorably.
Helene said yes, I and I checked off the mental box of having to worry about who my prom date was. A week out I got some pretty devastating news. Rumor was that Helene was taking someone else (Eric?) to the prom.
I don’t remember how she confirmed this to me, but I remember being one week out from my senior prom and dateless. I regrouped and asked my friend Amelia, who had dutifully attended every formal dance I’d ever needed a date for. She was also pretty, insanely athletic and extremely cool. As a bonus she was actually somebody that I knew, liked and talked to frequently.
The thing was, I realized that Helene probably wanted to say no in the first place. I mean, I guess it’s possible that she was also relieved to not have to “worry” about securing a date. It’s more likely that she felt bad about being asked and saying no.
That is precisely why I wish she would have. Not really for selfless reasons, although there’s undoubtedly a valuable conversation to be had here about boys, girls and consent. I wish she had said no for purely selfish reasons: because I’ve realized that making people comfortable saying no to me is vital to my success.
I can’t pinpoint the moment in my life where I first heard that it was good to “not take no for an answer”. I can tell you that in my current day to day as an entrepreneur (and a man) it’s something I see repetitively.
This kind of winner take all, adversarial and ultimately darwinist philosophy has a ton of appeal. We’re applying the transitive property of being right and success. If being right means you succeed, then it must mean that if you are successful that you are right. Therefore, whatever you to do get to the “right” outcome is also right.
In my last post, I talked about the value of waiting, which also runs contrary to this darwinist approach. Before you decided that I’m some kind of performative feminist trying to one-up my fellow men by eschewing all “traditional masculinity”, let me qualify it. I think aggression, confidence and determination are all worthy, positive traits.
When I look out at the landscape of messaging around this, I think those traits are being twisted into complete nonsense. They’re contorted into a rigid set of boundaries. They’re crushing creativity about the multitude of other paths forward you have when you face rejection. Perhaps nothing skewers this better than this SNL sketch from 2015 featuring Amy Schumer:
I like how I promised that I wouldn’t get into the sexual politics of this and then immediately turned sharply in that direction.
Let’s get to the point..
I met* my wife for the first time in 2005. For the purposes of this post I won’t explain that asterisk whatsoever. When we met we had a general sense of who the other person was, but had never had a meaningful conversation.
We were at a bar, the Friday after Thanksgiving, where people from our high school gathered when they were home from college. We spent thirty minutes or so talking that night, by my recollection. Then I tried to get her to leave with me.
She rejected me with an aplomb I’ve rarely seen in this world. It was like she couldn’t even believe I had the audacity to ask her.
This was the dawn of Facebook, and within six months we had dutifully made profiles on the exciting new world. At some point before the next Thanksgiving, she reached out and after a few messages suggested we meet up at the bar again the next year. I made plans and dutifully presented myself by the door so I couldn’t be missed.
She stood me up.
At both rejection points, I leaned into something that I had learned but not yet fully understood. It was good that she was comfortable saying no. It. meant that later, when she said yes: to being in a relationship with me, to getting married, to getting a joint cellular plan, that it was what she actually wanted. “No”, whether it’s painful or not, is an opportunity.
The opportunity is to transcend the ego of the moment. I think in both cases, I managed a joke, something I don’t advise most people do since there are many bad jokes you can make when facing rejection. If you must, I suggest something that isn’t at the expense of either party involved.
So, for example, let’s say you ask someone to go get Thai food with you, and they say no. You could always say “Yeah, I guess not everyone likes Thai”.
If you can actually honor and transcend the nervous stakes of the moment at which you propose a path forward with someone, you actually make yourself more likely to succeed. You see, when people are comfortable saying no, especially when they barely know you, they actually trust you.
Trust is not a half-bad starting point.