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Tales of a 30-Something Divorcé Navigating Costa Rica Dating

For a brief couple of years back in the 90s, I was a single man living in Costa Rica. Recently divorced, still in my 30s, in excellent physical condition, I was ready to live the dream as an eligible bachelor in Costa Rica! Daily, I rode my bicycle the few miles into town from the house I rented.

I spent a lot of time at an open air restaurant across from the town park. It was the best spot in town for people-watching. Sitting in my sweaty cycling clothes, sipping an ice tea if it was morning, a beer if it was afternoon, I smiled at any young woman who caught my eye and initiated a conversation when possible with those who smiled back.

The irony here was my cluelessness– I was the opposite of what the average Tica was looking for. I was recently divorced with two young children who stayed with me most weekends, had no car, and baked bread and cookies to sell at the beach and the local farmer’s market in order to pay my bills.

My bank account was in five figures– unfortunately, it was in colons, not dollars. The main piece of furniture in my house was a massive red work table of wood and metal that took up most of the living room. My bed was a mattress atop a piece of plywood atop a couple dozen arranged concrete blocks.

Not exactly Mr. Right. Still– I had an active dating life. There was the young woman who cut my hair. After my first visit, I decided I really liked my hair short. I went back for a trim every couple weeks until she agreed to go out with me. On our date night I borrowed a car from a friend. On the way home from our date, the car ran out of gas. She called her brother for a ride home. I let my hair grow out for months after. A waitress in my favorite beer and boca restaurant went out with me twice.

She loved my kids. In fact, she insisted I bring them along on our second date. She must have really wanted one of her own because the next time I saw her some months later she was pregnant. The father was a Dutch agricultural engineer who I knew because he always bought bread from me at the farmer’s market. He also drove a nice SUV and had a great job that no doubt paid well. She eventually married him and relocated to the Netherlands.

The young teller at the bank where I went occasionally to withdraw a few thousand colons (this was pre-debit card) was always sweet, friendly, and wanted to practice her English with me the brief time I was making the transaction. I offered to give her English lessons.

She accepted and we made the date for a Saturday afternoon. She showed up – with her husband. We had one impromptu 30-minute class. When they left all, I could do was laugh. I met a woman at the farmer’s market. She was friendly, but odd-looking and somewhat overweight. At this point I was not particular. We went on a date.

My friends who met her all had the same reaction: “She has a great personality!” I took her home later. We were met at the door by her mother and a brother, both of whom wanted to know where she had been. A few minutes of unhappy conversation revealed a Cinderella-like scenario, with my date being the oppressed one of the household, expected to do the drudge work.

Except there was no fairy godmother, no pumpkin turned into a carriage, no glass slipper, and I sure as hell wasn’t Prince Charming. I excused myself and disappeared into the night. All of the above were within a period of six months or so. Some months later I was in my favorite seat at the open-air restaurant, sipping a beer after a strenuous bike ride, when a young woman came to my table and asked if I could help her with an English assignment for a class.

We chatted and went on a date later that week. She later admitted that she and her friends sometimes joked about the sweaty grungy gringo they often saw wheeling his bicycle into the restaurant. On our first date I proved to her that I could ‘’clean up good’’. The next year we got married and are still together today.

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