Chapter 47: The Gentleman

Well, everyone, the moment has finally come. I have a story for you that is all good. Ladies and gentlemen, allow me to introduce you to Evan, The Gentleman. 


I know, I said I deleted my dating apps – and I did! – but dating in COVID-era Boston was proving to be virtually impossible. I took myself out on dates and to restaurants and things, dressed cute to go to the store, and nothing. So I figured I only had a couple of more months; I might as well go back on and get a few final Boston stories. Which I did, like in my last edition of One Hit Blunders. But then, I matched with Evan on Hinge. 

Evan just had a good look to him, besides being attractive and having a nice smile. He had pictures in suits, not shirtless gym selfies. Also, he had a picture with who I guessed was his mom, not a fish. Finally, he actually answered some of the prompts and seemed to have a good sense of humor. So I swiped right. And he had swiped right on me because we immediately matched. 
We started to talk and hit it off right away. We were finding things in common left and right, and he just seemed super decent. He has a good job that he actually enjoys, loves his family, has hobbies and interests, and made me laugh. A lot.

Slight side note, around this time I was also realizing how superficial a lot of my friendships in Boston were. When we couldn’t go out to bars as freely, I realized that a lot of my ‘friends’ weren’t really people I felt like I could just hang out with. Or they were constantly hanging out with each other but not inviting me. And honestly, it hurt. But at the same time, it reinforced my decision to move. It made me feel even better about my decision to leave a lot of things behind – in my 20s, in 2021, and in Boston. I promise this is important in a minute, but anyway, back to the story. 

I also liked that Evan made plans to hang out with me pretty quickly. And those plans involved taking me to a steakhouse. He was even patient when I was with family in North Carolina for Thanksgiving and couldn’t go out quite as soon as he wanted. When I got back to Boston, he made plans for the next week on Tuesday. 

man wearing suit jacket dress shirt and dress pants standing near wall
Photo by W R on Pexels.com

On that day, I hadn’t heard from him. This was a bit weird because he was usually really talkative so I checked in on him. I knew he’d gotten a COVID vaccine the day before so I thought that might be why, and I was right. He was feeling extremely under the weather and had slept most of the day. Evan asked if there was any chance I was free the next night. I did have a movie night planned, but we were able to reschedule to Tuesday, so Wednesday, my birthday, was officially free. So I figured why not break the biggest first-date rule EVER and go out on my birthday? 

I told Evan, yes, I could go out on Wednesday instead of Tuesday. But, that he couldn’t stand me up because it was my birthday. I made him promise not to make a big deal out of it, though. At the time he agreed, but on our date, things went a bit differently. 

He invited me to Del Frisco’s by the Seaport, where I’d never been, so I was excited. I took my time getting ready because I wanted to look nice – I mean, this was a steakhouse date, my birthday, AND likely my last date in Boston given my pending move. I wanted to dress to impress. 

Clearly, Evan appreciated it. When I walked in and found him at the bar, he was literally stunned. I’ve never had someone look at me like that. All he said was, “Wow.” And not going to lie, his pictures did not do him justice either. His eyes are seriously so blue, I couldn’t stop staring. 

We made our way to our table and he had me pick our bottle of wine. We had already decided on an Oregon red from 2017. First, I tried to pick the least expensive one but he quickly realized what I was doing and told me to pick the one I really wanted. I did. We also got some delicious steaks and lobster mac & cheese. Plus, he didn’t judge me at all for my love of rolls. 

He asked me tons of questions and I answered all of them. Our dinner lasted almost four hours. He had told me before we even sat down that he was just going to ask me anything and everything, and I don’t think there’s a single topic we didn’t discuss. He actually listened to my answers, even. I know this for a fact because several conversations before (over message) I’d mentioned how much I love cheesecake. When he went to the bathroom, he told the waitress (who he was EXTREMELY polite to – major bonus points) that it was my birthday and asked if I could get me cheesecake for dessert. And they did! I got some amazing, free cheesecake and it was an amazing end to our delicious dinner. 

After dinner, we walked out towards the water and I could tell Evan was close to ruining the moment by asking me the forbidden question. Quickly, I just told him – no, don’t ask. And he didn’t. 

We ended up going back to his place (get your mind out of the gutter) because, during dinner, he’d mentioned that he had been decorating his Christmas tree but needed help finishing it. I happen to be an expert Christmas tree decorator, so I offered my services. I helped him decorate his tree and then he paid for my Lyft home – truly, a gentleman. 

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