Matching in Many Ways

When I was forty-one, OkCupid was the first dating website that I used because Rachel recommended it. After using it for a while, I was curious about others, how they worked, how they determined when two people were a good match. I wondered if I could meet more people being on multiple websites and apps.

OkCupid had questions that I was encouraged to answer. Questions such as “Can you date someone messy?” or “Do you like to wear a costume for Halloween?” or “Would you rather cook your own food or order takeout?” or “Are you spiritual or religious?” or “What do you prefer to swim in?” or “How are you feeling about the 2020 election?” Basically, the website had all kinds of questions from serious to casual to silly. I answered some and skipped some. Some were easier to answer than others. I also kept some of the answers private to myself.

I also had to answer each question for “him.” What should my ideal guy’s answer be? I tried to think in the context of matching. For example, could I date someone messy? I considered myself fairly neat. How about him? Might he be clean or messy? And how important is this to me? Would I want to be unmatched from someone who answered he was messy because he did not put his dirty socks in the hamper? I thought if a man was kind and messy, I would still like to meet him. But if a man expected me to pick up his dirty socks every day, I wasn’t so sure. Who talks about dirty socks on the first date anyway? As I went on answering hundreds of questions for both of us, I gave “him” plenty of latitudes.

OkCupid took these answers plus the importance of the questions and calculated a matching percentage. Each man, or each profile, had a percentage of the match to me. There were thousands of questions and I didn’t answer that many. Initially, I liked the fun and simple questions but realized that hard questions were equally important. For fun, I liked the beach over the mountains. But important to me, I was not religious and didn’t want to date someone who required it.  At the end of the day, I didn’t go by these numbers all the time but used them as just one of the many indicators of a man’s compatibility to me. I believed that there was something between two human beings that might not be quantified into a neat mathematical equation and presented by a simple number.

The second website I tried was eHarmony. eHarmony had a very lengthy setup process. I sat in front of my computer and answered a three-hour assessment before I could be matched and see anyone.  They wanted to know my personality and preferences. The assessment included picking out words that I preferred and more than multiple-answer questions from OkCupid. After a day or two, I got my first few matches. For one of my matches, I decided to contact him. Then, I had to ask him questions which he could answer. When he answered my questions, he could also ask me questions. After that, we could decide to and were free to message freely. I didn’t like the heavy-handed process that guided the initial interaction between two people, which some people might find helpful. Perhaps because I started on OkCupid first and couldn’t let go of my limited dating habits from there. Soon, I stopped using this website.


The other two very popular new mobile apps were Tinder and Bumble. They didn’t have websites at all. I didn’t have any trouble signing up with both of these. It was easy and quick. Similar to OkCupid and eHarmony, I had to add my photos. But instead of writing up a full profile, I only needed to add captions to my photos or add a few short sentences about myself if I wanted to. The way these apps worked was based on how we meet people in real life, on first impressions of how one looked. On my phone, I saw pictures of a man, if I liked his photos or short burbs, I could show that I liked him by swiping right. When I didn’t like someone, I passed that person by swiping left.  Matches happened when both people liked each other or swipe right. Bumble worked similar to Tinder with one additional rule which was that women had 24 hours to message first after being matched. When I didn’t write first within 24 hours, that match disappeared. After I wrote the first messaged, he also had 24 hours to decide if he wanted to reciprocate my message.

After about 50 swipe lefts, I saw a man who went to UC Berkeley and Columbia Business School. Cute. Nice pictures. Cool. So I swiped right, so did he, and we matched.

“Nee how ma,” he texted first. 

“Hi. How are you?” I replied.  

“How do u say fine in Chinese?” I didn’t like how he assumed I was Chinese. To me, it was like assuming every white man is from England. But, hey, I didn’t want to read into it too much. 

“Han how. Lucky that I know Chinese to answer your question. It’s a beautiful day. Isn’t it? Just finished brunch with a girlfriend. Maybe heading to the MFA!” I was trying to change the subject, to see if I could see the goodness in him. 

“Very nice outside. How do you say, let’s get naked in Chinese?” 

“Maybe it’s a bit early to learn that!” I was totally offended now. I wanted to end the conversation as soon as possible.   

“<crying face emoji>” 

“Yes! Unfortunately! So you are interested in Chinese and getting naked.” I texted my final thought and unmatched him. 

Seriously, I had to laugh! 


Coffee Meets Bagel gave curated matches daily. I found the pace a bit slow. While Hinge found singles in my Facebook network. Happn showed singles near me in real-time as I moved around town. I didn’t get attached to any of these datings apps.

I was sure there were plenty of other online dating websites and apps, but after all the ones I tried, I thought I had a good idea of how different online dating websites and apps worked. However, contrary to what I thought, I didn’t meet more people with more websites and apps. I started seeing the same men on multiple dating sites. More was not better. 

I went back to using mostly OkCupid probably because that was what I was used to. Against my general rules, I paid for an additional premium A-List feature so I could see who liked me. Rachael and I had talked about this in detail. As a very general rule, men liked to make the first move. After scrolling through profiles after profiles liking people, I decided to look at only men who already liked me and didn’t have to like someone who hadn’t express interest in me.

Having the A-List felt like a short cut or cheating. Well, cheating or not, I call it curiosity. Why not? I’m sure you’ll find the guy to enjoy watching the clouds with you. If not, you’ll still enjoy a beautiful day,” Michael said.  “LOL! That doesn’t sound like cheating to me. Just data gathering!” Rachel said. 


By chance, I saw an acquaintance working at a matchmaking company. Curiously, I asked her what she did. She told me that set up the first dates for singles. The idea of having someone arrange my dates and doing searches for me was very appealing. Human brain vs. computer algorithm. Who would win? It also might mean that I get to meet a different pool of men from those I had been meeting through online websites. I made an appointment to officially speak to someone there. The woman answered all my questions. They would assign me a matchmaker based on what I was looking for. The matchmaker would screen potential candidates based on my criteria. The matchmaker would set up first dates for me, including a place to meet up. Those first dates would be blind dates. Unlike using dating websites, which was completely free, this would be an investment. I thought if I wanted to meet someone of quality, I might as try multiple ways. I decided to give a matchmaker a try. 

A few weeks later, I was assigned to Dorothy, my very own matchmaker. Dorothy set up a time to speak to me and get to know me better. She told me that this process would get better as we continued to work with each other. It took time to get to a person. After our one hour call, she sent me her list of questions to answer. She wanted to know everything about me. She also asked me about my availability for the next month or so. Then she was off to her searches. 

While I was in a meeting with my clients one morning, I got a text from Dorothy. @Dorothy: Hello Mindy, how are you? Are you still available this Thursday? I have an amazing guy for you! He’s smart, witty, a foodie and up for pretty much anything. Would love to send you both out Thursday at 7 pm to play some games and grab a beverage. Sound good?

@Mindy: Hey! Good to hear from you. Yes, I am still free Thursday night. That’s awesome! Games? I hope it’s not trivia. I am horrible at that! 

@Dorothy: Yeah! It’s the game cafe in Brookline. So much fun! and there are many options for games. grab a bunch and get to know Edward, your new friend. I’ll set it up. 

When she told me that I had a first date a few days before the meetup, I could not sit still. I asked Dorothy for information about that man. She did not tell me. She wanted me to get to know him the traditional way, meeting, and talking to each other in person. Without knowing anything about this man, not even a name, I was still giddy. I could not contain the excitement inside me.  

Dorothy told me the location of where we were meeting, a game cafe, which was not anywhere I would have picked. Even though the place was in my neighborhood, I had never noticed it. I was slightly concerned about the location. “Games?” I said to my friends. 

“My husband and I spent our whole first year of dating by playing trivial pursuit…and not talking. There’s hope for meeting over games. There are many more games than trivia! And have a drink to get the tongue loosened!” Rachel said. 

Games are fun! I went to a party last Fall where they had games. I found that I was quite competitive!”

“It sounds like it’s close to home so that’s good. Plus your there to get to know him, the game stuff is just a distraction.”

“I had a friend who’s name was Edward, he was a good guy. Wonder if this is the same Edward! He could be the one I know LOL…. No, this Edward I know lives in Europe. Have fun!”

“Haha! Maybe he is here for a visit?! No?” I responded. “When I first got the text of this blind date, I googled Edward who he might be. But other than the name, I didn’t have any details. So, I forgot about him and went back to work.” I also told my friends that it was probably going to be embarrassing because I was not good at games. We didn’t play games growing up. I would be out of my element. Drinks?! Will definitely have a couple! Did I make a mistake? I didn’t screen him? Games? I had not played a game in years! I might be able to beat him in card games?! Or distraction?! I wonder if I would focus on the game and forget about the guy!  It was starting to be fun to think about and this is-it-a-mistake gut feeling disappeared. Now it was a mystery to be solved!

 Okay, I could try this and see what happens.

At 5 pm on the day of the blind date, I got the following text:  

@Dorothy: Hey Mindy! Get ready for your upcoming date with Hans at 7:30 pm. What will you be wearing? 

@Mindy: Hey!! Just about wrapping up with work. Can finally relax and get in the mood for the blind date. Wearing a blue horizontal striped white summer dress. With white Vans! Should I wear my favorite jewelry too?! 

@Dorothy: Edward is wearing a blue polo shirt, jeans, and red shoes, will have a corded red strap attached to his camera. 

Red shoes? Okay. This is intriguing. Definitely unique. At first, I thought she was just being supportive and asking me what I was wearing. She asked so we could have something to recognize each other. 

At 5:30 pm, Dorothy mailed me: “Edward is a foodie!  He loves food.  Loves to try new restaurants, try new food out.  He’s for sure adventurous.  He is upbeat and loves to talk.  He would love to have the witty banter and conversations with a woman he is dating. He’s from Canada but his family is from Asia.  He is very close with his family and loves being able to spend time with each other.” 

Edward was there when I arrived at the game cafe. That impressed me: the quality of being on time. He had a big smile on his face when he saw me. He bought me a smoothie; there was no alcohol at this game cafe. He asked me what game I wanted to play. I picked Risk because I have heard of it. We at down near the front next to the window away from other people. He explained the rule. We set it up and went on talking for the rest of the hour. 

At the end of the date, as we walked out of the game cafe, Edward smiled and said, “How about we hug? I am a hug kind of guy!”

I summarized Edward to my friends:  Smart and articulate. Talkative. Studies health sciences. Worked in software consulting, but want to maybe start something new and stop doing strategy consulting. Thinks food in Boston sucks. Thinks Toronto has better food. Thinks having a zipcar membership is not the same as having his own car. Thinks Trump might get reelected because he is still speaking to his base. Need only 3 to 5 hours of sleep. Goes to bed at 1 pm. Thinks the game cafe is a weird place to meet. Gave me a hug when we said our goodbyes. 

I thought we had high-quality conversation and he had a great personality and was smart and passionate about his work! Unfortunately, I wasn’t attracted to him physically and did not feel any chemistry. 

I felt that Dorothy found the core of what I am looking for and was not off by much. I had a great time at my first blind date. I was happy that my first blind date was such a good experience.  I looked at the survey on my phone. I needed to reply. Do I want to see him again and give him my number? I didn’t want to waste our time if I was not interested. So I declined to see him again and gave my reasons. 

“I know the look is important but looks change. A little change in lifestyle, stop traveling, no more crazy work hours, and more time at the gym can totally change the way one looks. When I first met my husband, he was a stick, but after going to the gym, he’s more buff. A little love handle! All I’m saying is that keep an open mind. Sounds like you had fun regardless.” Rachel said. 

“I liked him up until the part where he thinks Boston food sucks.  Then he lost all of my support. Exciting!  Glad you had fun. And wow, she seems like she knows what she’s doing.  XO!”


After each date that didn’t work out, I didn’t look back and went on more dates. I kept meeting more single men, either matched by Dorothy or on dating websites or apps.

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