Serena Williams

American 1422, PBI to LAX, 10:18 a.m.

I was trying to stuff my bag in the overhead compartment. They designed those things to minimize the amount of stuff you can bring on board with you. Why? They want you to check that bag, because if you check that bag, you pay and they win. I ain’t havin’ that shit. I. Stuff. That. Bag. Every time.

Just as I was getting the bag with all my shit into the compartment that didn’t want it I heard, “Excuse me,” very politely said.

I turned, saw the woman standing outside the row I was in, and I immediately said, “You’re the greatest.”

I said that because I was looking at Serena Williams aka the greatest. I don’t think I’d ever been as starstruck.

As we took off I couldn’t help myself. I made small talk. “I can’t believe I’m sitting next to you.”

“Well, you are.” She was fun and clearly not taking herself too seriously. I asked if she lived in LA, and she told me she was only visiting because Florida was her primary home. Once we were at cruising altitude she opened her laptop and began taking notes. Lots of notes in a pad. After a while I asked what she was doing.

“School.”

“School? You’re in school?”

“Yeahhh. I’m taking classes.”

It never occurred to me that a superstar athlete might want to further their education, but at that moment I thought, Oh yeah, you can keep learning even when you’re successful. Cool.

We ended up talking a good while before she asked what I did. This is, of course, the norm on flights. People always ask what you do, and it doesn’t take long for comedians to realize that it’s not a good idea to tell strangers you’re a comedian. If you don’t know why, imagine how you would react if the person sitting next to you said that they were a comedian. You’re probably not done asking questions, right? When you’re first starting out it’s kind of cool to tell people. I mean you’re new to it too. It’s affirmation that you’re actually doing it, for real. It doesn’t take long for you to put together that if you tell people you work in comedy, they’re going to talk to you for the rest of the flight. And they’re going to have a lot to say. I’ve heard every type of question and comment from all types.

Comedy? I love comedy! You know, people say I’m pretty funny.

What kind of comedy do you do? Tell me a joke. Do you curse?

Are you on Saturday Night Live? I love SNL. Kristen Wiig was my favorite. Do you watch it?

Who are your favorite comics? What’s your style like? Have you seen this thing in the news with Syria? How would you joke about that?

Oops, I spilled on myself. I guess that’s going in your act, huh?

Yeah, I can’t wait to get to the stage tonight to tell them how you spilled coffee on your pants.

Most working comedians develop a reflex for dismissing any notion they’re a comedian on flights. I either say I work in “production” and like “creating schedules” or I say I work as a consultant in construction. Most people don’t have a lot of follow-ups on that. One time I thought I was clever and said I worked with “pens” as in the manufacturing of pens, and the guy had so many goddamn questions about pens, so I dropped that one.

But when Serena Williams asks what you do, you tell her the truth. Not just because it’s the right thing to do, but in this case, her asking me questions was welcomed. I was cool, but not too cool with it.

“I’m a comedian.”

Her reply?

“Anywhere I can watch you?”

I mean, that is the perfect response.

And I had the perfect reply. It was about a year after my first one-hour special had come out.

“I have a special on Netflix called Completely Normal.” She smiled and, get this, she wrote it down on her notepad. Then I spelled my name out and watched her write that down too.

It was a pretty cool moment. When we landed I asked her for a pic, which she was very sweet about. “I mean I don’t have on makeup and we just flew, but… okay.”

I was extremely pleased with myself as I walked through the airport toward ground transportation. I imagined Serena Williams would be watching my special Completely Normal that night.

Fuck!

At that moment it hit me. In that special I actually talk about Serena Williams! And what I say is exactly this:

“Oh, my God. I do think about death. I just want it to be justified, you know? Like, if I die violently, you know, maybe I have, like, Serena Williams sitting on my face, and… I don’t know, Venus is polishing me off, and they’re trying to fit a racket in my ass or something like that. Then my wife comes in, boom, and I’m, like, fucking done.”

Keep in mind I wasn’t saying this in an interview. It was during a stand-up performance. During stand-up we exaggerate, often in extreme ways, which is why a lot of people laugh. It’s not what you ever say in regular conversation. That’s the magic of a stand-up performance. In the act I was talking about only wanting to die if it were justified, worth it. Still, I was appalled, not that I’d said it, but that it could be interpreted by her as a not so hidden message from me.

“Hey, watch my special. I think you’ll like it.” Wink-wink!

It was absolutely not my intention to do that. I think both of the Williams sisters are lovely, inspiring, super-talented athletes, and what I say on the stage is not meant to translate into the real world. I really had forgotten about that bit, and now I had to process that I’d suggested to this woman I admire that she watch me talk about a threesome with her and her sister and an enormous apparatus shoved up my ass right before I die.

At that moment I wanted to die.

Of course, I never heard from Serena, but earlier this year I did run into her. I realize how casual I made that sound.

Ran into Serena at the store. Nice gal!

Not what I mean. I cannot believe that I ran into her after a show. She and her husband, who, I’m sure, didn’t tell her he wanted to die the same way I did, were a few feet ahead of me at a party. I was drunk and high when I spotted them—the perfect combination when you want to relive an embarrassing story with someone. I approached the two of them fifteen feet from the bar and held them captive as I retold the entire story above. My intention was to make them laugh. And it worked with Alexis, her husband, who was ear-to-ear smiling. Serena was politely listening, not as entertained as I’d hoped. Was it because she did watch and was remembering the bit? I felt a sweat start to build. It’s one that I’ve felt before.

Am I bombing?

At one point I could feel the shame working its way from my face down my body and I said to them, in a not-so-quiet voice, “I think I’m humiliating myself right now… I’ve been drinking.”

To which Serena replied, “We’re trying to get on your level. Where can we get a drink?”

I pointed to the bar.

I’m making you a promise. If I ever run into Serena Williams again I am not bringing any of this up.

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