Well, folks, the time has come. This is the story that I have been dreading writing about ever since I finally decided to bite the bullet and start this blog. 

As I’m sure you’ve realized by now, and like I have mentioned before, I typically use humor to mask my pain – and over the years I’ve gotten pretty good at it. But if you’ve come to love my blog for a laugh or two, some self-deprecation, and my amazing sense of humor, I’ll tell you right now that this chapter is not going to be like the rest. While I will try my best to sneak in a few jokes here and there, this story is still pretty recent, to me at least, and it still hurts a bit, so it might not have the same tone you’ve gotten used to. This is also one of those stories that no matter how hard I tried, I just couldn’t seem to condense into the usual length of these chapters without feeling like I wasn’t really telling the whole story the way it needs to be told in order to fully understand its impact.

But, what’s just as important to me as being funny and entertaining is being honest, and being real. In this chapter (okay, maybe it’s going to be a bit of a book), I will be 100% real. Sometimes, life sucks, a lot, but that’s just part of being human. To anyone else who’s experienced a particularly crappy heartbreak, you aren’t alone and I hope that this chapter helps you realize that.

So while I already have my big glass of wine to get me through writing this first part (which will most definitely take me at least a few days to finish), and I hope you do, too (I told you to get some ready last week!) – I’ve also taken the liberty of creating a playlist for you to enjoy while reading this chapter since I can already tell that it’s going to be a particularly long one. This playlist is meant to be listened to in the order I have it in to kind of parallel the story itself, but you can totally shuffle if that’s more your thing. If you don’t drink, grab some ice cream, if you don’t like ice cream, I don’t know what to tell you.

Also just a shameless plug for if you want to follow me on Spotify!

Alright, enough with the introduction. As always, all names have been changed to protect privacy. Let’s start the story of The Rollercoaster.


Earlier this year, I was back on Bumble, yet again, but so far had not been having a lot of luck. More than anything, I was just on there for entertainment and the occasional confidence boost, but really, I was kind of enjoying being single. I had finished grad school, I was about to start a cool new job where I’d get to travel, I felt healthy, and I was really happy with my life. 

I had recently read an article about astrology feng shui or something, talking about how your home can impact other areas of your life, so I was kind of taking that into account in my life as well. Not just for romantic reasons, but I felt like I was attracting a lot of positively at that time, and I wanted to keep that going. One of the things they said to do was to clear out clutter and make more space in your home, because more physical space meant you were also making more space for positive things to come into your life – and yes, that’s including love. 

red roller coaster
An actually fun rollercoaster.
Photo by Stas Knop on Pexels.com

Then one night in January, I was on Bumble and I ended up matching with Tony. His profile was literally perfect – no fish photos, no games of “guess who?,” good grammar – the works. He was insanely attractive, and seemed like a great guy. He’s a personal trainer and massage therapist, but also teaches kids with special needs, and his profile talked about how much he loves what he does (which is a major turn-on for me considering I’m very over the guys who don’t have any work ethic), and I was extremely excited when I got the alert that we had matched. 

I messaged him and asked him what his favorite food is – amazingly original, I know – but he responded with Italian, so I knew he was a keeper. It turned out that Tony is from the area, but now lives in Arizona, but was visiting Boston for the weekend. He asked me if I’d like to join him for drinks that night, and while for a moment or two I hesitated because I was kind of tired, I did end up saying yes.

However, I did almost end up late to meet because I got very invested in making myself some baked ziti and nearly thought about canceling, but something kept telling me that I couldn’t bail on this one. So, I ate my ziti very quickly, freshened up, and was on my way to the hotel he was staying at to meet him for some drinks.

I texted him that I was there, and he said he would come downstairs. The second I saw him, I froze. I have honestly never experienced anything like that before. I would say it’s kind of like the feeling I get when I unexpectedly see a picture of Liam Hemsworth and am reminded of how ridiculously sexy he is, but it was so much more. All my pre-date nerves immediately disappeared. I felt safe, I felt comfortable, I felt like this was it. This is what I’d been waiting for. I know that on the rare occasion when I fall for someone, I can fall hard but I swear I have never felt it so strongly or so quickly with anyone ever before. The way he smiled at me, I honestly felt like maybe he was feeling the same thing. It was the best feeling I’ve ever experienced. 

We sat down at the bar and ordered drinks, and immediately the conversation started flowing. I told him about having recently finished grad school, the job I was about to start, my family, and studying for the LSAT. He told me about his family – including his many sisters – and his job, what brought him to Arizona, and more. I will be the first to admit that I have NEVER been a big fan of Boston accents, but oh my goodness – his is perfect. I was hanging on his every word not just because I was already so into him but because I loved the way he said everything. We had a lot in common, he made me laugh, he laughed at my dumb jokes and sarcasm, and overall we were hitting it off. Really, I felt like I’d known him for years. He was genuinely interested in what I had to say, too, which was a breath of fresh air. 

He asked me if I wanted to come out with his friends after we finished our drinks, since they were in town and he wanted to see them, too, but he wanted to spend time with me since he was heading back to Arizona the next day. I agreed, so we went up to his room where I met one of his friends, we hung out there for a bit, and then headed over to Earl’s in the Prudential Center to meet the rest of his friends.

I liked them immediately. They all seemed so nice, and not at all put off by him bringing some random girl along – which I would have totally understood if they didn’t like. They welcomed me, made me feel comfortable and not like an outsider, and they seemed to really like Tony and think of him as a good guy. We all got along, so it was a good night and it made me feel even more comfortable with everything. I also thought it was absolutely adorable that he kept bragging about me to his friends and making them congratulate me on having just finished grad school.

As the night went on, and I had a couple of Moscow Mules (with gin instead of vodka – try it, I got Tony to and he liked it) in me, the liquid courage started coming out. Earlier, I had asked Tony if he wanted to see my apartment after drinks because I was talking about my rooftop views, and he said yes. Our chairs started to get a little closer, hands started getting touching under the table, and I was really excited. Not in a sexual sense, in a, “I really want to get to know him better” kind of way. Finally, he and his friends were talking about something they all had to do the next day and I leaned in and asked him if he was still coming to my place after. He said yes, after we were all done. Maybe it was the alcohol, or maybe it was just the connection I was already feeling, but I got a surge of boldness and whispered to him, “Oh, but I kind of want to go now.” With that, he told his friends we had to go and said good night. I told them goodbye and thanked them for letting me crash their evening, and we headed out.

On our way to the Uber, I said something about being an Empath, I don’t remember why, and he said he knew. I asked how he knew I was an Empath and he said that he’s one, too. I warned him that this does mean I’m prone to crying and feeling all the feels, and he said that was okay. He understood and said that he thought that was amazing. I think that was the first time I’ve told a guy what an emotional little thing I can be sometimes and he didn’t freak out over it or get weird about me admitting that I cry like at least once a day for no reason. While we were outside waiting, the “old me” that felt like I always needed to be sexual to keep a guy interested in me broke out for a second, and I asked him what his favorite position is. Tony replied, “This one” as he wrapped his arms around me from behind and gave me a kiss on the cheek. It was the cutest thing ever, I for sure swooned a little bit when he said that.

I remember the whole way back, I kept saying, “I never usually do this,” which I guess isn’t exactly true, but in a way, I felt like it was going to be the first something that I hadn’t done before. I kept asking if he’d think less of me, and made him swear not to think differently about me, that this was just because he was leaving the next day, and he assured me that he wouldn’t. I made him swear. He swore it was okay, he liked my confidence, he felt a connection, too, and he wouldn’t think any less of me for acting on what we both wanted.

Tony kissed me for the first time on my apartment building’s rooftop deck. I remember the exact spot. You know that “foot-popping” I’ve mentioned before? That was the first one I ever had. I mean, I didn’t literally pop my foot, but I felt it. It was very different from the way I’ve been kissed before. I remember at one point I was looking at the view, which is pretty amazing, and I looked back at him and I caught him looking at me smiling. You know that scene in “Tangled” when Rapunzel is looking at the floating lanterns, and Flynn is looking at her and you probably thought to yourself that you wanted a guy to look at you that way? That’s exactly what it was like.

We went back to my place and talked some more before things led to where I’m sure you can imagine they did. I asked him not to go right away because I didn’t want to feel like a prostitute or like I was being used, so he stayed a while longer. We had some laughs, I felt more comfortable than I ever have before, and really, it was just perfect. We cuddled a lot, and then he had to go but told me that I should come visit him in Arizona anytime, and said that we’d hang out next time he was in town. I believed him. He asked me to walk him downstairs and I did, and right before he left he gave me another big hug, a kiss, and said he couldn’t wait to see me again. 

I was over the moon happy. I fell asleep like a little kid going to Disney World the next day. I was already feeling the beginning of this being more than a crush or lust, but I really felt like it was okay. I was so convinced that this would be it. When he texted me first thing the next morning, not making me doubt for even a second that this was just going to be a one-night-stand he bragged about to his friends, I was even more sure.

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