Top 5 Most Horrifying Post-Divorce Dates

I stuck with online for two long years before I found the delicious new man in my life. Along the way, I had good dates, bad dates, interesting dates and depressing dates. I also had some memorably strange first dates.
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Detail view of two business people's legs under a coffee table while in a meeting outdoors, using a cell phone.
Detail view of two business people's legs under a coffee table while in a meeting outdoors, using a cell phone.

After my marriage ended, I was alone for a long time. Eventually, I plucked up the courage to date again. Friends urged me to go online. Like many people, I was curious but apprehensive. Once I started reading online profiles, I was hooked. There were so many people, so many choices. And each week, new ones magically appeared, kind of like the cake factory scene in that old I Love Lucy episode where an endless stream of confections keeps coming down the line.

I stuck with it for two long years before I found the delicious new man in my life. Along the way, I had good dates, bad dates, interesting dates and depressing dates. I also had some memorably strange first dates.

What follows are my top five most horrifying first dates from this time period. I share them here not only for readers who are amused by odd human encounters, but to hopefully inspire those trudging the online trenches. You are not alone. Horrible dates happen to all of us. Keep your sense of humor and keep going -- it will get better!

1. The Pet Date. After a brief phone conversation, I met a man at the Santa Monica Pier on a Sunday afternoon. He had a dog with him, a nervous looking mutt with very long ears and very short legs. "It's my ex-wife's," he explained. "I look after it when she goes out of town." He glanced at me like he thought I'd think he was a nice guy for doing that. I tried to stay neutral, though by now, the dog was jumping on my pants in a really irritating way. We started down the boardwalk, the dog skittering back and forth like it was trying to trip me. My date seemed oblivious. His phone rang. "It's my ex-wife," he said, like it was Joe Biden calling. A heated argument ensued as the ex harangued him for not taking the dog to the dog park as instructed. He got off the phone and launched into a rant about what a bitch she was and how she'd told him he was bad in bed. "Why on earth do you babysit this woman's dog?" I asked. "If I don't, she'll make me take it to a pet motel," he said. "And I'm sick of paying for it!" I didn't go online for at least three days.

2. The Sad Widower. I'd noticed there were a lot of widowers online. They seemed nice and non-threatening and I'd emailed with several. I'd even sent a couple of condolences. Finally, I decided to meet one, a man who had sent a heartfelt email in which he confided he badly needed to live again. We had a nice conversation and the date seemed to be going well. Two drinks later, he leaned closer and said that if we became an item, we'd always have to go to my house. "Oh? Why's that?" I said, wondering how we got to this topic so fast. He grinned boyishly and revealed that he and his wife still lived in the same house but led separate lives. I was, as they say in the U.K., gobsmacked. "Why did you say you were a widower?!" "If I said I was still married, no one would want to go out with me," he replied. "Women like widowers."

3. The Blind Date. A friend knew we were both online dating and thought we might be a match. His profile revealed that he was a good-looking media spokesperson for a high-end dog food company. He was going to be in our city and my friend had arranged for me to pick him up so he could take me to dinner. I arrived at his motel and called from the car. "I'm not ready yet," he said. "Will you come up?" My friend knew this man fairly well, so I went up to his room and knocked on the door. The door opened to reveal Mr. Kibble standing there stark naked and very relaxed about it. I was proud of myself in that moment. Even though I felt primitive heart-pounding fear, I stayed calm as the part of me that revels in strange moments clapped her hands with a gleeful, "I don't believe this!" "I see you're not dressed yet," I said demurely. "I'll be in the car." I walked to the parking lot, quelling my urge to run like the wind, then drove home.

4. Going Dutch. I met him in a noisy little sports bar. I ordered a chardonnay. He ordered coffee. We had little in common. It was all pretty benign except for one startling moment when he dropped into the conversation that his mother made him put his hand in her vagina starting at age four. After the requisite 45 minutes I said I had to go home. He paid the check and we left. An hour later, I received a very long, angry email. He wrote that he felt very annoyed with himself and with me. He was sick of feeling taken advantage of by people and not speaking up. He was referring to my letting him pay the check. Jeez, I only had a $5 glass of house wine! He railed me for not paying for my drink and ended by firmly stating that on all our future dates we would be going dutch thank you very much!

5. Hidden Agendas. He suggested we meet for at a wonderful little Japanese restaurant. There was no attraction but we chatted and the food was excellent. "Do you always have a wonderful dinner on a first date?" I asked. "No," he said. He'd read on my profile that I was a therapist and thought I could help him. He was obsessively in love with a woman in Minneapolis. He hadn't seen her in seven months and it was killing him. I popped a spring roll in my mouth and gently explained I couldn't conduct therapy under these conditions. But I said he could just talk if he wanted and I'd just keep eating -- which I did, and then went home.

If you've had a horrifying first date, please share below. No names but lots of juicy details please!

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