There's Nothing Quite Like Meeting Amy Winehouse's Father To Inspire A Little YOLO On A Second Date

And, yes, by YOLO I mean sex.

Feb 6, 2013 at 9:00am | Leave a comment

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With Amy Winehouse's father Mitch and Tony Bennett at a benefit for the foundation in her name.

For our date on Monday, the Comedian texted me asking me if I liked playing pool. I said I did, but I also had an invite to a benefit for the Amy Winehouse Foundation thrown by Charlie Chaplin's granddaughter Kiera Chaplin. He texted, "That's so funny. I was asking because Buster Keaton's great granddaughter is having a pool tournament to benefit the Kurt Cobain Foundation. Small world."

This dude is funny. We met up at my place, and my dog Sam jumped up on him excitedly. Impressively, he then taught Sam how to sit before getting a reward of praise or opening the door to go outside. While I grabbed my purse, the Comedian led Sam out front, and I was charmed.

We had dinner at an Italian restaurant and then headed to the Electric Room. Before I had a chance to say, holy shit, that's 86-year-old Tony Bennett looking boss as hell, Amy's father started speaking to the crowd about his daughter's final song with Bennett "Body and Soul."

When he learned she was doing that particular song, Mitch Winehouse recalled telling Amy: "'That's my favorite.' And she said, 'I know that. That's why I chose it.' So I said, 'Do you know the words?' And she said, 'You've been singing it to me for 25 years, dad. Of course I know the words.' And, you know, if Amy had to have made a last recording, to make that last recording with the greatest male singer of all time, Mr. Tony Bennett. Then what could be greater than that?"

I got chills when he spoke, and he seemed so madly in love with his beautiful daughter, still.

After the tribute was over, the Comedian kissed me, asked if I was having fun, put his arm around me and I was struck again by his gentleness. "Let's get out of here," I said.

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Kiera Chaplin, world ambassador for the Amy Winehouse Foundation, actress, model and granddaughter of Charlie Chaplin.

We arrived back at my place and -- oh, my blessed not-yet-crate-trained-dog -- were immediately greeted by Sam's poop scattered near but not necessarily quite on the Wee-Wee Pad I left out for him. "Sorry," I said, and he held Sam back on the bed as I cleaned it up -- with the paper towels he brought me on our first date. "Hey," he said, as Sam looked quizzically up at his loving restraint. "I get to see my paper towels in action."

"Thanks for holding him," I said. "This would be a lot more interesting if I were wearing like a French maid outfit or something."

"All good," he said. "You know, we're just couple of dudes, bro-ing out."

After taking Sam around the block, we did the whole lead the dog to the bathroom thing, and then we kissed on my bed. Sam continued his low yowling as he had the other time, but this time it wasn't as bad as the first.

"Oh, man," the Comedian said, laughing. "What if this becomes a thing for me? Like, every time I hear a dog crying I get hard."

I laughed. I find myself very attracted to this guy. Physicality doesn't feel mechanical, but it feels soft and luxurious and delicate and exciting. Finding that right balance of two people both being into one another is so difficult -- there's often an imbalance, but when it's fairly even on both sides, there's a rare electric giddiness and a sweetness that is narcotic.

At one point, he said to me when I pulled away and stared at him, "What are you thinking?" I didn't say anything but just smiled. "I can't give everything away," I said. "Oh, yeah," he said. And then in a very funny actorly whisper he said, "You're so mysterious," and we both cracked up. "That's me," I said. "Super fucking mysterious."

"I mean, it's like," he continued, "I just don't know anything about you."

I couldn't stop laughing.

After a certain point, he decided to spend the night, and I really -- honestly -- didn't think I was going to have sex with him. I really didn't. We were just going to go to bed. We retrieved Sam out of the bathroom, and the Comedian tried to sell Sam on how awesome the bottom of the bed was. Sam wasn't buying it. He kept crawling between the two of us so that every time the Comedian tried to put his arms around me, he put his arms around Sam, too. I must say, Sam looked incredibly pleased with himself.

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Oh Sam.

We finally positioned it so that Sam was on his side, and then we started talking. We couldn't stop talking. I love people who I can't imagine boring me because the riffing potential is like crack cocaine itself. We were talking about one of my favorite topics: what makes videos go viral. I mentioned this great profile of Ricky Van Veen in New York magazine, where Ricky talked about the "formula" that College Humor uses. Then we pulled up videos and were watching them together, and after a while, I shut down the computer so we could truly fall asleep. It was 1 in the morning. He stroked my arm, we looked at each other and then we started kissing -- again.

At one point, early into this seduction, Sam started licking his arm. I knew this because the Comedian said, "Um. Your dog. He's licking my arm." Then he pulled the blanket over us, and we made a fort of blankets, but because I have a very intelligent dog, Sam started barking tentatively. Word to the wise. You really can't build a blanket fort without inviting this dog. It's just not done. The Comedian laughed and led Sam to the bathroom again. And by this point, the tingliness extended all over my body, and I was honestly feeling very YOLO about the whole damned thing and life is short and Amy Winehouse and, well, so I decided -- as the bathroom door clicked shut -- that I might sleep with him. I might.

There's something about going to any kind of memorial that very much puts you in the motherfucking moment. Earlier in the evening, we had also found ourselves talking about people we knew in comedy who had died too young: Richard Jeni, Greg Giraldo, Patrice O'Neal, Mitch Hedberg. He told me about seeing Chris Rock perform right after Jeni killed himself and Rock, who was very close to Jeni, did this brilliant bit on stage about how stupid it was that all these people were mourning the man who didn't even know him. Rock told the audience that he actually was a close friend of Jeni's -- and know what was he going to do? Go to a Lakers game, that's what. And he knew Jeni would be there looking down. "You know why?" Rock asked the audience.

Because life is for the living.

As we fooled around, and the YOLO was really kicking in, I also realized this guy wasn't the type to really give a shit about the whole make-them-wait-a-year-for-it game. I trusted my instincts and finally let him pull down my stockings.

For however much I might write about it, I haven't had sex in many months. Most people just aren't worth it. And he was. It was tender and intense and wonderful. Afterward I went to the restroom and let Sam out, and I took a while getting ready for bed again. When I finally came out, the Comedian was kind of cracking up to himself, holding the condom and saying, "I just spent the last 5 minutes convincing Sam that he actually doesn't want this. Oh, and speaking of which, where's your trash can?"

I laughed. Fucking Sam. Comic relief, always.

When we went to bed for real for real, it took some reconfiguring to get Sam to not wedge in between us again, and my dog finally settled on the Comedian's side again. We kept talking for a little bit, and at one point, the Comedian turned to me and said, "So, your dog is, like, kicking and twitching next to me."

"Oh, sure," I said proudly, "he does that in his sleep."

"Wow," he said, adjusting to the sensation. "It's like having a warm shaky backpack."

God, this guy makes me laugh.

In the morning, I asked if he liked coffee and, oh, he did, how funny, me too, so did he think he would go to Starbucks and get us some? "Oh, no, no, no," he said, "I'm not the errand boy this early in the relationship."

"Interesting," I said. "I guess I'm just the kind of person who likes to do nice things for other people."

"You know, you are very entertaining when you don't get your way," he said. "How about we go to get coffee together."

I got up and started to get dressed reluctantly. "Aw," he said. "It's our first fight."

I grinned, and we walked Sam over to Starbucks together. After he came outside with our two coffees, we then circled around the block once more, and he kissed me goodbye in front of my door. "So. Are you free Friday?" he asked.

I sipped my coffee and smiled. Sam sat obediently next to me.

"Yes," I said.