If you had asked me to go on a date with someone who had just gotten out of prison, my answer would be an immediate no. I'm not someone with Bonnie and Clyde syndrome and have never initiated anything with a known ex-con. My dad used to make fun of me for being a rule-follower, almost to a fault. I hated it when I double parked or ignored posted signs.
Then I met Mr. Hollywood on a dating app.
As I get older, using dating apps puts me in a smaller and smaller mating group. Most men my age or younger are dating younger people or are married and looking for something on the side. I am a meditator who eats healthy foods and is quite artistic. I haven't made a fortune yet and I want to find a partner, not a lover.
I'm not everyone's style. Men no longer look at me as a woman to mold. They just see that I don't drink, I don't smoke and that I'm no longer a pin-up.
I was intrigued by Mr. Hollywood. It was nice. He had a nice profile that represented a clean and slightly geeky guy. He was more of a computer technician than a Miami drug dealer. His profile showed that he enjoyed the outdoors, was a fit runner, enjoyed movies, and had homes in two states. His children liked him and he seemed kind.
When he sent me a rose, I thought: why not meet him? We texted and then talked so I was pretty sure he wasn't cheating on me, that's very common now on dating apps. He immediately invited me to dinner. That was different. Almost no one did that. Coffee, of course. A walk, perhaps. Committing to an early night out felt good. It's been a long time since anyone asked. I said yes.
Then he sent me something to read.
“Let's see if you still want to meet me after reading this,” he said. I was a little reluctant to click on a link. Potential scammers on LinkedIn have sent me private messages with job URLs that may or may not have been real. (I usually delete them rather than find out.) So why would I trust a link from some random guy that I interacted with only on my phone?
Instead, I searched for his name and the title of the article and easily found what I was looking for. He had been in prison for selling drugs. He had been in prison for selling drugs. The article definitely sided with Mr. Hollywood and his business partner. It said, in a nutshell, that they had been wrongly accused of being “kingpins” and did not deserve their 20-year sentences. Well, I thought, this won't be a boring dinner. I would like to hear your story.
He set the date for the first night he would be back in Los Angeles and I gave him some restaurant ideas. He picked one near me in Santa Monica. That was nice. I could walk there.
I learned that he discovered he was autistic in middle age, but always thought he was neurodivergent, even if that term wasn't yet in the zeitgeist. I found it charming. He pulled out my chair and showed the right degree of interest. He was the perfect gentleman, plus he had a great Hollywood producer. Producing films was his passion; Selling drugs supposedly made him a lot of money to dedicate himself to it.
He loved his dinner. The conversation flowed. He slyly said “I'm not a good person” so innocuously that my old self would have missed it. Current me heard it as a Rebound ringtone.
Before dinner, he would have thought that sentence was his wounded self, needing love and attention to heal. I was raised by a sweet, overbearing father who would have said something derogatory about himself to get me to help him with his computer or read fine print. I used to run in and take on the helping role because it offered warmth and a modicum of love. That pattern never worked in relationships and it was exactly what I wasn't looking for.
But the sentence passed quickly and he seemed genuinely interested in maybe working together. He even said during dinner something like, “I feel like we have a collaborative vibe at work more than a romantic one.”
I agreed. But then he said he was very attracted to me. It was nice to hear it. The flattery was quickly silenced. He revealed that he could soon return to prison. Another court date was approaching.
When the date ended, he made sure that I would be okay returning home on my own and asked me to send him a specific script I had written, which also served as the text “Yes, I made it home safely.” I later looked up more information to see what I had missed about him. Aside from a couple of giant red flags, our dinner was a fun date, something I haven't had in a long time. Instead of feeling disappointed, I felt more hopeful about dating in general.
I sent him the script and he replied that he would read it soon. I followed up a couple weeks later and he said he was woefully behind. Unlike the men I'd dated, the ones who cajoled me knowing we weren't couple material, he simply never contacted me again.
I didn't feel rejected. I felt like I had gently slipped away after a nice dinner. His approach was not criminal. It was closer to heroic. I hope you find a Bonnie for your Clyde and live a long and happy life.
The author has written live action and animated scripts. She lives in Los Angeles.
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