Chapter 46: One Hit Blunders, VIII


Jay was another person I met on Hinge as part of my “Farewell to Boston” tour, and he ended up being my last terrible date in Boston. I mean, I had to have one more, right? 

Jay seemed normal enough over Hinge, so I agreed to meet him for a drink when he asked me out. The first red flag was that he picked a place only a few minutes away from him but quite the trek from me, but I figured I was trying to go to new places, might as well try it out. The second was that he wanted to meet at what’s pretty much my bedtime, but on the day of, I asked if we could meet earlier, and we agreed. 

Despite us agreeing on a new time hours before and him living only five minutes away, I was there more than fifteen minutes before him. What is it with guys showing up so late? Honestly, I almost left, but he showed up right as I was about to. It turned out that he’s a regular at the bar he chose, and pretty much everyone there knew him, and that just kind of rubbed me the wrong way. It’s OK to have a favorite spot, but it made me wonder how much he drinks to be so known there.

I won’t even bore you with all the details of the date, but let’s just say it sucked. When I told Jay about my recent trip to Greece, he basically called me stupid for traveling alone and said, “as a woman,” I should never do stuff like that. When I explained where I was moving and why he proceeded to judge me for my life decisions and criticize everything I’d just said. We talked about travel destinations we want to go to, and I said how much I love elephants but would never go to one of those places you can ride them, as cool as it would be because I disagree with treating animals like that. And he laughed at me for caring about animals. Yeah, lack of compassion for animals is not a good look and a huge deal-breaker. 

tasty refreshing drink with ice on light background
Photo by Geraud pfeiffer on

After drinks, we started walking around the block, and he started leading me down a street that was a bit darker and less crowded, and I had this overwhelming feeling that I needed to get myself out of there. Why I don’t know, but I just had a bad feeling, and I wanted to go home. 

However, around that same point, Jay broke my cardinal rule and asked to kiss me. Obviously, given the lack of chemistry and enjoyment throughout the night, and my hatred of being asked, I said no. He did not take it well, which proved my feeling correct. He kept trying to ask after I’d said no, and I finally just said I wanted to go home. 

Because I said no, he gave me grief the short walk back to the main road and then refused to walk me to the T stop. I did try to give him a sort of “thank you” hug, but he just stood there. Super awkward. 

 By the time I got home, I had a nasty text from him about not knowing that asking for a kiss was “such a vibe killer.” I didn’t really think there was a vibe to kill, and I was annoyed with his attitude throughout the night, so I gave a sassy response in return. I mean, would you expect anything less from me? After my reply, he did the typical “try to guilt her because I’m single and don’t know why ” spiel, but I just shut it down and thanked him for the drink and went to bed. Sorry, Jay, you might be a regular at that bar, but not in my heart. 

So that brings me ALMOST to the end of my Boston dating life. While I talked to a couple of other guys on Hinge before I left, I only went out with one other guy. And, he gets his own chapter because not only did he take me out on my birthday, he made up for every awful date I’ve been on in Boston. A definite high-note. 

Until that chapter, I wish everyone a happy, healthy, and safe new year! Here’s to 2022 bringing us everything we want – love, abundance, adventure, etc. – and more!

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