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In 2015, a little more than a year before being stood up by Adam, when I was forty-one, single, had never been married, had no kids nor pets, I decided to start dating and dating online, something I had never really done before, with nudges from my friends.
On a sunny weekend morning in the summer, I called Rachel to meet up for brunch. We decided to meet up at Sonsie on Newbury Street. We sat at one of the oval table facing the open window looking out to the street, pedestrians, and cars. The sunshine and fresh air were wonderful. I ordered French toasts, one of my go-to’s and she ordered salmon benedict. The food didn’t take very long to come. Of course, we both ordered our coffees.
“How are you?” she asked affectionately.
“I’m very good. Glad to be back in Boston after having an amazing time in Taiwan!”
“Did you make friends there?” Rachel had experience living outside of Boston and the US as well.
“My friend from high school was there too. That was cool! I got in touch with a few classmates from elementary school. I hung out with a couple of them quite a lot. I also met people through my cousin Chao. I felt I had friends!”
“Did you try to meet guys there?”
“Not really. Most people I met were a lot younger. Interestingly enough, I met many single women my age.”
“What about trying online dating?” Rachel had met her husband online. She’d gotten me signed up with OkCupid a few years before, but nothing came out of it. I was not into it at the time.
“Maybe! I tried last time,” I said frankly and half-heartedly. Dating was never on my to-do list.
“Well, you didn’t really…” she said with a small smile around the corner of her mouth.
“Okay. You are right. I didn’t.” Rachel knew me well. I was intrigued this time. I thought about my couple friends and the husbands in my circle. I wouldn’t mind meeting someone like Michael, someone who was like us. The time felt right. Why not! I decided that I would now try to meet single men.
Michael also spoke of online dating favorably. “You’re such a catch! Men would love to meet you!” I told him he was too kind to say so. He always wanted me to find someone and didn’t like seeing me alone.
I didn’t know how to date and definitely had no experience dating online. In my twenties and thirties, the single men I met who might be interested in me all came and went. Having a relationship was just not something on my mind in the past. Now I didn’t know any eligible single male friends who I could meet and weren’t already friends.
Now, after Rachel and Michael had repeatedly brought up online dating again, I was curious and in the right mindset to consider it again after having almost two years of mindful days in Taipei. I could try it; there was no harm in trying and seeing what might happen. Mentally, I finally felt ready to meet single men.
So unlike the first time, I made myself think about and put more effort into my online profile. I opened OkCupid on my computer and followed the steps to recreate an account. I uploaded more recent photos, wrote a short paragraph about myself, and answered questions about me and “him.” I didn’t have any technical problems signing up with an online dating website. But I found myself wondering. How does this work? I was embarrassed to look at profiles of men and being asked to judge someone I did not know with a quick yes or no. I don’t want to judge anyone! So I waited.
Nothing happened for a few weeks.
“So how is online dating going?” Rachel checked on me.
“Nothing. I don’t think anyone is interested,” I said ready to accept it as a fact.
“Can I see it? Let me take a look at your profile.”
I handed over my phone to Rachel.
“You need better photos!” she said honestly.
“Really? I don’t have other pictures. What kind of pictures do I need?!”
“I can take pictures of you! Let’s go out one weekend!” I felt silly and excited at the same time.
That weekend, Rachel and I spent a few hours along the Charles River. I sat on a swing, in front of an old tree trunk, and on a park bench while Rachel made me laugh in front of the camera, the only way a good friend could. I liked quite a few of the photos she took. Okay. Better photos, checked.
“What about your profile?” Rachel asked a few days later. “You should write more about yourself. And answer more questions. That will help with matching,” she instructed.
“Okay.” I felt comforted that I was being guided by a good friend who had the best intentions.
I uploaded the new photos and rewrote my description as if I was speaking to Rachel about myself. It reminded me of something I read once about obituaries: Live your life according to how you want your obituary to read. I wrote more openly about myself such as reading books, watching movies, and listening to music. The top six things I could not do without were family and friends, books, my passport, sundresses, oceans, and sushi.
A few days later, I started getting messages.