From Messages To First Dates (#3)

Previous post: Getting Online (#2)

The first person messaged me was a 48-year-old Jewish Ben living in Jamaica Plain working in finance.

“Nice profile,” Ben said first.

“Beautiful picture! Where is it?” I said.

“Arcadia, Maine. I just moved from Brookline. Where do you live?”

“I am in Brookline. Near Star. Where were you in Brookline?”  I asked.

“St. Paul Street.”

“Why did you move?” I was curious.

“I wanted a bigger place. I looked in Brookline and JP. I like the place in JP.”

“What’s your top three favorite or memorable places in the world? From all your travels. I don’t have enough time to go to all the places that are interesting to me in the world. Is JP working out?” I said.

He didn’t respond back. That was the first and last conversation. I realized that I did switch the topic on him.

Shortly after I started online dating, I wrote regularly to a group of close friends telling them about all my dating stories. I was excited about meeting new people and to share my adventures with my friends who all cared and hoped for the best for me. When I questioned myself, “Was I too serious too quickly with Ben?” Rachael and Michael both jumped in, “You weren’t. Your question wasn’t strange or serious. You were just trying to get to know him! Just move on because he wasn’t the one!”

Carter messaged me and I read his profile. This was what he said in his profile. First, my profile picture is me with my two adorable nieces, not two women I am courting with. Geez, I am not that dumb! Secondly, I am not 45, I am 55. “How dare you!” you might say! Well, women in my age range usually don’t want to go out with me. They say I look too young. I want to show up in the right searches.” I messaged back since I messaged everyone back at the beginning. The conversation didn’t go very far. I found him a bit weird, plus he purposely listed a younger age. I didn’t feel good about that. Was the age a sign that I should have noticed early on? Rachael and Michael both told me that I didn’t have to respond to every single message I received. They are right. This is not a work email!

Then I had a few more conversations like this one that didn’t go anywhere. Either the man or I stopped writing based on whatever subtle feelings we were getting through messages. I told Rachel and she said, “you can’t decide about someone after 5 minutes of an IM conversation!” Rachel also told me, “Mindy, you gotta go out with someone and not just messaging! Nothing is ever going to happen if you don’t meet up!”

Donny, 44 and living in Boston, wrote Dear Mindy. Sorry to hear about the loss of your cat. Where did you grow up and what do you like doing in your free time?” His headline in his profile was “I am an active, intelligent, kind guy who is looking for someone for a great connection and, hopefully, a long-term relationship.” He had graduated from medical school and was current in real estate. I liked his first message. He read my profile and picked up on what I cared about.

“Hi. That’s okay. It’s a while ago, and Daisy has a good home now. I grew up in Asia and New England. I have a feeling my free time is not packed with as many sporty things as you do. Med school to real estate??” I messaged back.

“Yes, it’s true. I was an internist for 12 years and then transitioned into real estate a couple of years ago. The reasons for the transition are long and complicated for an email. The short version is that I got hit by the perfect storm of changes in the healthcare system that impacted internist disproportionately.”

“Glad you made the transition that you wanted! Not easy, I am sure. I work at a digital consultancy for healthcare technology. Pretty happy about that! Having success in meeting people here?”

“I am not having success finding people who I want to meet let alone meeting people here. I suppose that is part of internet dating. Shall we try to meet up and get to know one another face to face sometime next week over drinks?” Donny said. That was quick! I don’t have any concerns.

“Yes, I would like that.” And we went on to decide on a date, time, and place.

I was excited about progressing along the online dating journey and actually interacting with a real person. Finally!

Rachael said to me before I left home, “Good luck Mindy! I hope you have a good time. If it’s not going well…home is close by.”

I arrived at Barcelona early like I usually did. I picked a corner seat at the bar which was U shaped. My heart was pounding. How do I know who he is? I checked his photo on my phone one more time. A few minutes after our agreed time, I hadn’t seen anyone walking in looking for someone. I texted him. He said, “I am here. At the bar.” I looked up and so did he from across from the other side of the bar. Our eyes met. We both smiled and waved at each other. My immediate reaction was he looked better in his pictures. Within seconds, I knew I wasn’t attracted to him. Next time, make sure there is a full-body photo!

He walked over still smiling, he has a great smile, and sat next to me. I realized then that he was shorter than me. We ordered a couple of tapas dishes and drinks. He told me about his passion for art and music. He also built his own wine cellar at home. I told him about books and my travels. After an hour of great conversation, Donny offered to pick up the check, we sort of hugged, which I wasn’t prepared for, and said our goodbyes.

Alright. Unlike the men I’d met organically before in all my life, the intention here was crystal clear. Donny and I met on an online dating website. He was looking for a woman and I was looking for a man for a relationship. That was why we were online. I asked myself,  Do I like him?  This was all new to me. I didn’t have a checklist or a lot of concrete things in mind. I had no experience in this. My only criteria for meeting anyone had always been to look for kindness. I’d never had to be thoughtful about whom I met because I’d met people through schools and work that didn’t involve emotions right away. I hadn’t approach anyone with a romantic intent in more than a decade.

After I got home, I turned to my friends for help! I emailed them all about my date with Donny. I told them how I felt honestly.

“Hi All, I am safely at home now and did not get kidnapped by a serial killer. Donny was interesting. He has been dancing Latin for the last ten years. Very knowledgable about wine. Gave me lots of tips. Had lots to say about the issue with our health care system – well, how doctors are not being paid. He seems like a really nice person. Got me to try a glass of wine that I like. Paid for our drinks tonight. Perfect gentleman. Grows his own tomato, basil, etc in his patio. But … I am not attracted to him. Sigh!”

Michael had hope, “Attraction can grow.” Rachel said, “If you are not attracted to him, you are not.” I sided with Rachael. She is right.“Yes, I am moving on!”  Even though I feel bad! I had trouble being honest with my feelings and thoughts with myself.

My friends were my safety net both emotionally and physically. Before I headed out to meet Donny, I let them know where I was going and whom I was meeting. I told them details of Donny, his name, his phone number, and his photos. I thought I would never know when I might get kidnapped! Interestingly I found out later, my single guy friends never thought this way.

Since my first message with Donny to our first date, I emailed a “Dating Episode” to my close friends. Responding to what I wrote, my friends emailed back with their comments either encouraging me to continue on or agreeing with me that this guy was not worth my time. Michael said at one point, “These men don’t have a chance. They don’t know you have an army behind you!” Even though I was single, I was not dating alone. I felt safe, supported, and had fun and lots of good laughs. 

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