(How do you like that aggressively counterintuitive title???)

Every time I reach a major milestone, I realize what I was doing wrong all those years of trying to get there. 

Take college graduation. I’ll never forget sitting down to a breakfast bagel my last week of senior year, looking around my dorm’s dining room, and realizing, I forgot to meet all these people! I’ll bet most of them are cool. 

I’d made some good friends freshman year and prided myself on “not being superficial” … but oh duh. I ignored the fact that small talk is the gateway to a real friendship.

When I was leaving Los Angeles, I realized I’d forgotten to go to the beach and ride my bike on the Strand every weekend like I’d envisioned. Actually, why didn’t I live in Hermosa Beach? 

I’d thought I had to spend all my time near the Hollywood improv theaters, because I was “serious about comedy.” (That’s a whole other blog post.) And a commute from the South Bay would have been too exhausting, I said. But living by the beach might have made me more balanced? 

And so it goes with dating. Now that I’m turning that metaphorical page, I realize I could have had so much more fun with the process.  

I learned this by accident in New Orleans. A friend of mine really wanted to meet a guy, and I was like, “Go up and talk to him!” And she said, “You do it!” 

And the rest of the story is this blog post. 

I am not a natural flirt. The best way to prove this is the fact that I once talked a policeman into giving me a more expensive ticket, all because I tried to explain to him, with really good logic, why he was wrong. 

When I was single, my strategy was typically to ignore anyone until he talked to me. (Good luck with that if you live in Los Angeles!) In New York, this plan works OK because you wind up smashed next to someone and inevitably start talking to each other, even if it’s just to say, “Is there a hook by your knee for my purse?” (Thanks, population density!) 

Anyway, back to New Orleans. Because I had nothing to lose, and my only goal was to have fun with my friend, and because Eric was right there, I actually did start talking to people.

And I discovered a new side of myself: the side that can pick something positive about a strange dude, and say whatever pops into my head. We tried this every night we went out. 

These are things I actually said: 

* You look like you play football. Do you?
* Why aren’t you dancing???
* I love your shirt! 

Do you see the thruline?

These lines are all sweet but STUPID. 

More importantly, they worked every night. I’d start a conversation with the guy, then I’d say, “Oh, you have to meet my friends!” And disappear. 

Amazing!

When I was single, I had no idea it was that simple to start a conversation with someone I wanted to meet, because I’d always overthink it, or be afraid of sounding cheezy, or of not adhering to something I’d read in a self-help book, or whatever. 

Obviously, my own story worked out anyway.

But when I broaden out this lens, and look at these lessons, there is a pattern of taking it all too seriously and not enjoying the process enough.

I remember once doing a two-peson comedy show with my good friend Daisy and I think I drove her crazy because I was so intense and stressy. She’s never said that explicitly; but looking at myself it’s hard to imagine how I could have created any other outcome. 

“You just have to enjoy the process, Kerry,” she’d say. At the time, I interpreted that as, “Let’s not work so hard.”

We were talking about this recently and I reminded her of how she said that and was right.

“The process is all I’ve got,” she said. “If I don’t enjoy that, then I’ve got nothing.”

And that my friends, is the real lesson I need to keep relearning, in every chapter of my life.