When I was 19 and had just left college, I tried all sorts of things to make myself feel better. My amazing parents humored me in every one of them. When I decided that a big bouquet of fresh flowers in my room would make me happy, they let me go to Whole Foods and buy all the gorgeous organic flowers I wanted. And when I decided that I needed to make my childhood bedroom more “me,” they let me thrift all the pretty vintage furniture I wanted.

On one of my thrifting trips, I met a man. He followed me into the store and pretended to look around until I had made my purchases and then offered to carry my furniture to my car for me. Then he asked me for my number.

We went on a date the next night. He was actually really cool, and we had a lot of fun. But he lived in Wilmington, Delaware. We dated casually for several months. He would come down to visit me in DC on weekends. It was nice.

Then I started dating someone else, and our relationship slowed down. Eventually we lost touch.

Two years later, I got an email from him. He said that he was sorry he hasn’t been in touch, but he had been thinking about me. We decided to get coffee. And we had a lovely time. I tried to remember why we had ever stopped dating. I couldn’t.

Over coffee, he told me that he hadn’t been in touch for the last two years because he had been in prison. Ok, I thought, people go to prison for lots of different reasons. That wasn’t a dealbreaker.

I asked him why he had gone. He told me a story about how he had gone home with a woman, and then when her fiancé came home unexpectedly, she had said he was a burglar. I knew that was a bullshit story. But I figured he was sensitive about his imprisonment, and he was really repentant and eager to start over in a good way, so I just let it go.

We dated for three or four months. He lived in Philly, but I’d go up there (he couldn’t come to me because of the terms of his parole). He mentioned a few more bullshit things about his crime – like that it was a misdemeanor (right, you end up in prison for two years for a misdemeanor? My mom’s a judge, and I’m not stupid) – but I let it go. After all, he had pleaded guilty and done his time.

Then we were on the phone one night and he told me that he was falling in love with me. I really liked him and had some feelings for him, too, so that felt really good. But I decided it was time that I knew the whole story.

“Ok, D_____,” I said, “what did you actually go to prison for?”

He hesitated, and then told me that he had broken into a woman’s house and touched her in her sleep. He was a convicted sex offender.

That was what he pleaded guilty to. And I’m not a judge’s daughter if I don’t know how plea bargains work – prosecutors offer a reduced charge and a reduced sentence if the criminal pleads guilty. He pleaded guilty. To sexual assault. That means that, most likely, what he actually did was worse.

“Why, why wouldn’t you tell me that upfront?” I asked.

“I thought you would leave me,” he said.

I tried. I thought about it. After all, he had done his time and he was repentant. But ultimately, what he had done just wasn’t something I could live with. So I ended things.

I still get mail from him sometimes, always telling me that he doesn’t expect a response, but that he misses me and thinks about me. It’s kind of sweet and sad, until I remember that he raped a woman.