A year after my divorce, I wanted to dip my toe back into dating. Just my toe. No diving. No swimming. Just a dip.
I wanted to see “Close Encounters of the Third Kind” at the ArcLight in Santa Monica, share an espresso martini at Paloma on Abbot Kinney Boulevard, take my dog hiking up the Mandeville Canyon Fire Road and dance under the stars to Earth, Wind & Fire at the Hollywood Bowl.
Guess what? I did just that.
Then, at a little film school gathering at my friend’s house somewhere in Boyle Heights, I saw a friend from graduate school from across the room. I had not seen him in over 20 years. We had moved separately to L.A. to work in the movie business. The last time we saw each other, he took me to a Clippers game, and while I thought the date was splendid, he disappeared on me after he found out I was casually dating a big Hollywood film director. I was in my 20s, and practicing consciously dating rather than hopping from one serious relationship to the next.
Seeing him now, he was just as funny, flirtatious and tall as I had remembered, but maybe a few pounds heavier. Someone asked him if he was dating anyone, and he said, “No, but do you know any girls with low self-esteem you can set me up with?”
I laughed. Admittedly, it was a little too loud. I always loved his self-deprecating humor.
He noticed me. I asked him how he had been all these years. He said he had been a tortured screenwriter and reality TV producer for many years, but he had left the business to start distributing alcohol and was excited to be an entrepreneur even at 51 years old.
I asked if I could test all his beverages, which he had brought to the reunion like a good salesman, and I gave him an A plus on his tequila and a B plus on the branding.
After that night, we began spending time together, but just as friends. He’s a foodie and introduced me to a bunch of new restaurants. We shared Blueberry Cloud French Toast at Sweet Maple in Santa Monica and spanakopita from Loukà in Beverly Hills. We hiked the Mandeville Canyon Fire Road and did Sweat Pilates in Santa Monica.
He got me out and about in a way I hadn’t experienced since my divorce (or the COVID pandemic). I had been in hibernation mode for way too long.
I felt alive again.
I began to see myself as Erica (played by Diane Keaton) in the 2003 film “Something’s Gotta Give.” I was the independent woman in my early 50s who had all but given up on love since my divorce when I met Harry (Jack Nicholson), a fun chief executive in his 50s or 60s who had never married or had kids and had only dated women under 30.
Like Erica, I was not even thinking about dating. Like Harry, my guy had never married or been in a long-term commitment or had children of his own. He was the perpetual bachelor.
Some of my girlfriends thought that might be a red flag. One said, “A man does not grow up until he has kids of his own.” I noted their opinions but tucked them away in my head for a rainy day. I was busy learning to do magic tricks with cards with him, making tasty cocktails with his product, riding e-scooters on Olympic Boulevard and watching the Lakers play the Minnesota Timberwolves.
We even took our first Waymo together to see a movie at the Laemmle Santa Monica. We turned the tunes on full blast, and neither of us had laughed that hard in years.
One night, he asked me to go to Bar Chloe in Santa Monica for wine and pizza. I was excited to go, probably too excited in retrospect — like someone who had never been out before — but that’s OK.
I bring enthusiasm, I thought. I couldn’t help but think that this might turn into something more. That night, he gently placed his hand on mine and told me he wanted to see where this went. I felt butterflies.
Having zero experience in dating in over 20 years, I just blurted out, “I know we are both older, but are you 100% sure you want to be with me? You have never even had kids. Even at 51, you still can. You are a guy. There are tons of old dads in L.A. It’s normal here.”
I stopped talking. I realized I was nervous and not filtering my words very well.
He just said, “I’m good. I want this. Let’s see where things go.” And just like that, we were a couple.
Cut to eight months later — on our last date. He had been a little more distant than usual. We saw “The Naked Gun” at the Culver City theater. We both love slapstick comedies, but he seemed antsy when I tried to hold his hand.
I thought he might be stressed about something at work. A few days later, I asked him if something was on his mind, and in a somber tone, he said, “I really like you, and you check all the boxes of what I am looking for.”
When I heard “boxes,” I froze. Is that how he sees me, as boxes to check off? He was still talking. “You are beautiful and funny. I don’t think I have ever laughed with anyone as much as you. You are smart …”
Wait, I thought. These words don’t feel like compliments. They feel like I am being rejected on a bad reality show like “Love Island.” I can’t believe people really talk like this in real life!
My mind flashed to the moment in “Something’s Gotta Give” when Harry says, “Erica, you are a woman to love.”
It is an odd moment in the film because he doesn’t say, “I love you,” but instead insinuates that she is a woman someone else should love. It’s at once removed and so hurtful. Oh no, I thought, my Harry is breaking up with me.
Then I heard him say, “I want kids more than anything in the world. I think we should just be friends.”
And like that, it was over.
What could I say? I could not fault him for wanting kids. I had argued for it before we even began dating. We are at different stages in our lives. I am thinking about where my daughter might go to college, not preschool. He is thinking about coaching Little League, not the next act of his life. Who am I to stand in the way of his dreams? I quickly realized I was not going to get my Hollywood ending.
But I don’t want to end on a sad note because I still feel good about having opened myself up to someone again after a 15-year marriage, and now I can brag that I am an NBA, Waymo, e-scooter, cocktail-making expert extraordinaire on my dating app profile, and perhaps I can still find another version of Harry (with kids already) to vacation with in Paris.
The author is a former film producer who’s finishing her master of arts in clinical psychology. She writes about movies and psychology on Substack and Instagram @reeltherapywithkendall.
L.A. Affairs chronicles the search for romantic love in all its glorious expressions in the L.A. area, and we want to hear your true story. We pay $400 for a published essay. Email [email protected]. You can find submission guidelines here. You can find past columns here.
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