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Boston: Exploring Online Dating

By on December 14, 2015 in Men with 2 Comments

Temple Street, Boston“Dating is about finding out who you are and who others are. If you show up in a masquerade outfit, neither is going to happen.” – Henry Cloud

I grew up on the North Shore of Massachusetts, but I have spent over a decade living in warmer climates. A few months ago, I moved back. I have been settling in, as well as reconnecting with family and friends.

As some of the bigger pieces of my life have fallen into place, I have started to explore the social aspects. I decided to check out online dating and joined Match, OK Cupid, Plenty of Fish, and Tinder.

Going online can be overwhelming. As soon as men see I am active, I get bombarded with emails, chat pop-ups, and whatever else the site offers. I am keeping an open mind, but I am also trying to do a better job at filtering out non-interests and organizing possibilities. I have chatted with a handful of guys and gone on a few dates. I am focusing on quality as opposed to quantity.

What am I looking for? A guy I am comfortable with, where conversation comes easily and pauses are natural. Where flirting is instinctive, and I ask questions because I am curious and not just trying to make conversation. There has to be a click and attraction that cannot be defined, but is just there. The guy also has to have a kind heart, have similar values, be intelligent/clever, and be interesting/intriguing. These things give me butterflies.

Online Dating PicturesWhat is online dating like? It is all over the place. There are the nice guys, but the conversations are stiff and unnatural. There are the 20-year-old guys who tell me I could be a “cougar” (how insulting). There are the guys who make inappropriate, sexual comments. To avoid negative attention, I picked pictures showing different aspects of my personality and looks, but nothing I would consider sexy. I experienced one scam, where the guy who looked great on paper was stuck in Africa and locked out of his bank account. I reported the incident to OK Cupid right away. There was the guy who friend requested me on Facebook (after Googling me) because he wanted to get to “know me better,” but did not want to actually talk to me. To me, this is voyeurism, and I refuse to accept friend requests of people I have not met. There was the one guy who flipped out on me when he asked when I would be available, and I told him after Memorial Day weekend since I would be away. Obviously, we did not meet up. For the most part, the guys I have met in person have been really nice… except for one.

Of course, the mean man was sweet at first. We exchanged a few emails, texts and phone calls. He asked what I was doing, and I told him I was meeting a friend for lunch at 1:00 p.m. He asked if I could stop by Whole Foods and say, “hi” on my way to Newbury Street “a little after 12:00 p.m.” Although the timing was tight, I agreed knowing the following week would be busy. He had a nice voice, and the conversation flowed.

After getting lost, I arrived at 12:15 p.m. He texted me, and I informed him I had overshot the place and would be there soon. We did not meet, and I received some pretty nasty texts. At first, I felt guilty for “being late,” so I bought into his accusations. The little voice inside of me said, “red flag,” but I ignored it. I walked to Newbury Street pretty stressed out. We worked things out, but I knew the exchange was not a good sign.

Later on, we texted some more and decided to meet up. Why did I proceed? Curiosity. When he called, I kept trying to end the call ‘so I could charge my phone.’ I had already lost interest, but I had not yet admitted this to myself. I wanted to see if I was the one who should have been more cognizant of time or if he was the one in the wrong.

I was going to find a coffee shop and let him know when I arrived. When I was close, he asked me to meet him on his street. I did. He wanted me to hang out at his house with him until his laundry was finished, and then we could grab a drink. I told him I was not comfortable with this plan since I did not know him. I had already told him this several times throughout the day. We could not come to an agreement, so I went home.

A little after 9:30 p.m., he invited me to watch a movie at his place. By this point, I had lost any interest and realized I had done nothing wrong. I told him we were two different people and explained why. He got mean. The insults came flying, and I went from being “beautiful” to him explaining he wanted to hang out at his house because he “was embarrassed to be seen with me.” He flip flopped between insulting my physical appearance, swearing, and calling me names to begging me to go to his place. I was tempted to send him the definition of dissociative identity disorder (multiple personality disorder), but I did not want to stoop to his level and start name calling. I was finally able to end the exchange when I outsmarted him. I guess I just needed to stand up for myself and not succumb to his taunts.

Hanover Street Park in Boston, MA  Hanover Street Park, Boston

I am still looking. There is one guy I recently met on Match who I have a lot in common with, and I hope to see him again. There is also a guy on Tinder who captured my attention with his intriguing conversation and love of international travel. We shall see…

Note: Since I originally wrote this blog, I have removed myself from Tinder. As for the guy from Match… Nothing happened. To be continued…

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  1. Deb says:

    Ugh. I’m sorry! Great stories though!!!

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