Chapter 12: The Lost Boyfriend

One of the other first few guys that I met and went out with after everything with Al came crashing down was a guy that I matched with on Hinge who was looking for someone to take to a wedding in November… in Italy. I figured he was joking, so I went with it, plus, I love Italy, so that was an instant conversation starter. 

Roy seemed nice, he was very funny and he loved Disney – which is a major plus in my book. We talked on the app for a few days, where our mutual love of Disney helped us quickly bond. That’s when he told me that if I loved Disney, then I’d probably heard of him when he had a moment of being infamous in the Disney world. This obviously intrigued me, so when he said that he’d tell me about it on our first date, I was very excited.

For our first date, we went to Rocco’s Tacos in the Seaport, which was really good and I recommend it if you haven’t been! We got drinks first, and that’s when he told me that he was known throughout one of the Disney groups that I belonged to for something embarrassing/funny that had happened with him and his ex-girlfriend one of the last times he went. I remembered the story (got to love those 15 minutes of fame), and thought it was pretty hilarious that this was him. I told my friends, and they agreed that only I would end up meeting and going out on a date with someone like him.

Then we got our tacos, and when it came time to pay, I offered to split it (like I always do) and he agreed. I do give him a bit of a break because I knew that he’d recently left his job to do something he was more passionate about, but at the same time, I’m kind of old-fashioned, and I really think that if a guy asks you out, he should pay on the first date. It makes you feel courted and special and like you’re worth a few $2.75 tacos and a drink, you know? Plus, if I’m being totally honest, I’m kind of spoiled when it comes to that as 99% of my guy friends refuse to let me pay for myself if I’m out with them, and pretty much any guy I’ve been on a date with has insisted on paying for me. So, I was a bit put off but didn’t want to use it as an excuse to completely write him off. And, he seemed nice and very into me, so I wanted to give him another chance. 

After our tacos, we walked around for a while, and then he offered to drive me home. While we were driving, we probably broke so many rules about not talking about or exes or unloading our baggage on the first date, but it seemed to sort of make sense. He’s a Leo, so it seemed a lot more like we were just comfortable with each other (since we’re both Fire signs) than anything too crazy. 

We hung out another day not too long after, we realized we were both doing some shopping in the same area so we shopped, got smoothies, walked around the waterfront, and then ended up getting dinner in the North End. That time he did pay, which I appreciated. That was the first day he kissed me. It was not the foot popping kiss I was looking for, but it wasn’t bad. I think that was the night that I took him to my apartment’s rooftop lounge (which is kind of my ‘thing’) and some guys were CLEARLY talking about me in another language and staring at me, and maybe doing some sort of mating dance? I don’t know, it was odd. We had a good laugh over it either way. 

Photo by Hana Brannigan on

He was super nice, and since during this time I was in training for Encore, he was very thoughtful and offered to pick me up and drive me home a couple of the nights that I got out late. One of those nights, I kissed him good night to try to see if I felt anything more than a platonic feeling towards him. I didn’t.

So at that point, I felt bad because I could tell that he had fallen hard but I knew that I was not nearly on his level. One night, while I was at Vivianne’s goodbye party before she moved, he drunkenly professed his love for me so I knew I was going to have to do something about it before it got too far. He must have a Cancer Moon or Cancer Rising, because there’s something about these guys falling for me so quickly. 

The thing is, I knew he really didn’t love me, he loved the idea of me – especially considering his previous relationship. I also just knew that we were going to be way better off as friends, we got along so much better that way. We have very different views on some things, and I could tell that ultimately, we were not going to be very compatible in some really important areas. I tried to tell him this one time, but I don’t know if I really said it the best way possible. I’m just REALLY bad at rejecting people because I feel so bad for hurting their feelings, I over explain and go on tangents and it just gets complicated to the point that I think I completely miss the point of what I was trying to say. But, I try! 

One of the last times we hung out, my friend from work Celia had asked me to go out with her and this guy that she’d been going out with, but didn’t want to send the wrong message to or anything, so she essentially needed a buffer. This was kind of perfect, because Roy had been asking me to hang out but I was afraid that if we were to hang out one on one he’d get the wrong idea, so I asked him if he wanted to come out with us, and he said yes.

The four of us had a really fun time, all things considered! Unfortunately, when he tried to kiss me goodbye I turned my head and made it super awkward. That’s when he realized that I’d kind of done the same thing to him that Celia had done to her date, which I did feel bad for, but sort of like with PJ, I just didn’t know how to make it any more obvious that I wasn’t interested in pursuing anything romantic, and I really just don’t get why guys have to see a girl wanting to be friends as an open invitation to keep trying. It makes me uncomfortable, so I needed to see how he was in a group setting before agreeing to another one on one thing. 

After that, we kind of drifted apart. We do still pop up in each other’s DMs every so often, and I did text to jokingly call him out when a few weeks later, he ended up matching with Celia on Hinge and used the EXACT same line that he’d used on me. I thought it was pretty funny, honestly. 

And that is the story of Lost Boyfriend. If you notice the nickname and follow any Disney groups, you should be able to figure out what exactly his claim to infamy is in the Disney Passholder group, and how I picked his name. My Disney friends thought it was pretty funny that I ended up going out with him in Boston, of all places, and that he kind of sort of fell in love with me for a time. It really is such a small world after all.