friends Archives • Madeline Olsen

Chapter 24: The Rollercoaster

Not as much fun as it sounds.

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.

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.

Pages: 12345678910

Chapter 17: One Hit Blunders, Part II – The Italian Stallion and The Smoker

Welcome back to One Hit Blunders. Part II brings us to two gentlemen, The Italian Stallion and The Smoker.

For our first story, let’s take it back to when I was still living in Orlando, around the beginning of 2018 – so, not too long before I left, but at a time when I was still kind of hoping for something, or someone, to give me a reason to stay. Which is when I met Mario, or as my friend Charlotte dubbed him, The Italian Stallion.

Mario and I matched on Tinder, and if you couldn’t tell by the name, he’s Italian. If you didn’t guess by now, I very rarely date/go after Caucasian American men for some reason. In high school, I very much went for the blonde, Abercrombie model ‘lax bro’ types, and then suddenly in college I realized that actually, I didn’t really like those kinds of guys. That’s what my friends liked, and I went along with it because it was the style back in the day. But, really, I was into dark hair, accents, and dad bods. But I digress.

So, Mario was Italian, and his pictures made him look decently tall, he had a nice smile, and overall, seemed nice. He also worked at Disney, so we had that in common, and his broken English was kind of adorable. We made plans to go out, with him inviting me to go get pizza at MidiCi because he loved it. I thought it was kind of stereotypical to go get pizza with an Italian guy, but I love pizza, and I’m not picky, so I went with it.

We met up after talking for a few days, and honestly I was pretty excited to meet! But guess what? I had yet another height liar. Whoever Mario had to take his photos did a great job with angles because he looked about 6” taller than he actually is. He also managed to hide the fact that he was severely balding despite only being barely 30 years old. Again, not deal breakers but just be honest!

I’m in a serious relationship with pizza.
Photo by Vincent Rivaud on Pexels.com

The meal itself was okay, but he spent most of it talking about how he called his family still in Italy multiple times a day. Kind of cute, but also kind of not, in my opinion. Mario just seemed like way more of a mama’s boy than I was prepared to take on. The pizza was good, though. After we ate, we walked around the shopping center for a bit and ended up getting Starbucks tea (after he told me he doesn’t like their coffee) and then it was time for me to head home. On the way back to my car, though, I saw his car… well, van. He had some sort of large white van that he bought so that he could fit his whole family in it if/when they came to visit. I’m not really into materialistic things, but a large white van is not exactly a chick magnet.

After that date not really emitting the spark I was looking for, I figured we’d just slowly drift apart, but he, apparently, did not. He kept trying to see me, and I was trying so hard to be nice about it. One day, I decided to go to Epcot with two of my coworkers, Charlotte and Bianca, after work and I was telling them that Mario worked there. I made the mistake of telling Mario that I’d be in the park, and he literally sat and waited 20 minutes after getting out of work for me to get to where he was, just to say hi. Meanwhile, Charlotte and Bianca were on my phone scrolling and swiping through Tinder to live vicariously through me. It was when they eventually met him that afternoon that Charlotte dubbed him The Italian Stallion (it was an ironic nickname, obviously).

What makes all of this even MORE hilarious is that eventually, Mario and I drifted apart and he didn’t text me so much anymore, and then, I found out that Charlotte’s little sister, who worked in Epcot, was telling her that one of the guys she worked with was basically in love with her, asking her to move to Italy with him, or saying he’d stay here for her, and Charlotte figured out that it was Mario. So, sorry for her sister that she became the new object of his affection for a while, but it worked out for me.

The second part of this chapter, The Smoker, is a pretty short story, to be honest. Dev was another guy that I matched with on Hinge and overall, he seemed really cool so we set up plans for a date. He brought me flowers, which was pretty adorable, and then we went to Kings to play pool and have something to eat.

But he kept commenting on how bad I was at pool even after I had disclosed this information several times. He also drank a bit more than I would drink on a first date, personally. Then, we went to the dining portion of it and he made another comment on the fact that I ordered a burger, and because of that, he made the executive decision after I placed my order that we’d just share my fries. Um, I did not agree to that? It felt weird and like it was his way of showing his disapproval of my weight or body type, or the fact that I, you know, eat? He also clearly doesn’t know that this girl right here does NOT share her fries with just anyone. That’s something for my inner circle only.

The conversation was lacking, but for whatever reason I agreed to go ahead and take a bit of a walk with him afterwards. On the walk, he asked me if it was okay if he smoked, I answered honestly, no. That didn’t sit well with him apparently because he was pretty cold towards me the rest of the night. Dev also took this time to start talking about how great it was when he sometimes couldn’t sleep and would go for walks late at night, and then chastised me when I said I didn’t before going on a tangent about how great it is and how I should do it, before I finally reminded him that, you know, I’m a girl so me walking around the city by myself in the middle of the night just sounds like the start of an SVU episode.

Finally, I decided to call it a night and ordered an Uber to pick me up a couple of blocks away. He waited with me, and lit up a cigarette literally the second I got in the car. He did text me later to ask me out again, and I said thanks but no thanks, and he was very gracious about it, but ultimately smoking is a huge deal breaker for me, as are comments about what I eat.

So, that brings us to the conclusion of Part II of One Hit Blunders. Stay tuned to see what comes up next!

Chapter 11: The Host

When I was on my second College Program in 2015, I ended up meeting a guy about my age who worked in a different department, but was helping out in Innoventions (where I worked) during one of the festivals. He seemed nice, so we started talking, and I told him that I really wanted to work in his department someday. He offered to tell me more about it and give me some advice on getting into it, which I thought was really nice, so we exchanged numbers after lunch one day and started to make plans to hang out some night.

Of course, this was a big “no-no” as far as Christian was concerned. He was “talking to” another girl that had caused him to extend his target demographic by another year, so I figured that meant I could do whatever I wanted, too. I told him excitedly that I’d met this guy who was going to give me advice, and seemed really cool, et cetera, and he asked what his name was. I told him his name was Chad and he simply said, “Nope.” I asked him why, and allegedly, Chad had a somewhat shady history with a girl who worked at Innoventions a year or two before me, and so everyone who worked there had a weird vendetta against him because of it. Christian even had one of my friends/coworkers who was off that day text me telling me all the reasons why I couldn’t go out with Chad, and said that everyone at Innoventions would hate me if I did (ironically, most of them already did hate me and secretly wanted to ruin my life, just behind my back and not to my face. If only I’d have found that out months earlier).

But, unfortunately, I was still in my phase of listening to everything Christian said. So, I ghosted Chad. Just stopped answering his texts, blocked his number, and avoided him if he walked through Innoventions. I felt bad, but as far as I knew, he was bad news, and Lord knows I didn’t need any more of that in my life.

A couple of years later, in 2017, my dream came true. I got a Professional Internship position working in Guest Relations at Disney World. And, of course, because I’m a one-park-pony, it was back at Epcot. I was extremely excited to be back at Disney after cheating with Universal for a bit, happy to be back in my home and favorite park, and looking forward to meeting new people and learning new things.

I never thought about if I would know anyone that was still in Guest Relations, but of course, I did. My first day of training I met the girl I’d be training with, Lucia, who’s still one of my best friends (and my soulmate), then my trainer, and then Lucia’s trainer walked in. And who was it? Chad, of course.

I couldn’t tell if he recognized me, but to be fair, my hair had gone through about three or four different color changes since I last saw him. We trained in our little pairs for the remainder of the week, and everything went well. Over the course of that internship, I learned that really, Chad wasn’t so bad. He was very sarcastic and had a similar sense of humor to me, helpful when I had questions, and overall just seemed like a decent guy. I tried to tell Christian this and that he was wrong about him, but of course he just told me more lies and made up more stuff. But at least this time, I didn’t listen, and I continued to have some sort of friendly working relationship with Chad. I ran into him a few times after my internship when I was in my last position at Disney, and it was always nice, so I thought that it was cool that after all that time, we could at least be friendly.

For a long time, that was the extent of our friendship. We occasionally liked each other’s photos on Instagram, maybe a message or two here and there, but nothing crazy. Then one day, I was bored and decided to ask him if he had remembered me from Innoventions when I walked in to Guest Relations. He claims he doesn’t remember, which is fair, but I guess that just sort of opened up some sort of door with us because after that, we started talking a bit more.

Eventually, he started to get flirtier, and I often did, too, but I didn’t always bite until after The Cheater left me in a moment of need. Then, my grandma – who was one of my best friends – passed away just a couple of days later. I stayed in Florida for a few more days and then flew back to Boston to get back to my life. The day I got back to work, my managers pulled me in for a meeting and said that they had to let me go because my position was being eliminated due to budget issues. Way to kick a girl when she’s down, right?

So after all that, I was really sad. I felt lonely, lost, and I was desperate for a distraction. So, I started to entertain the idea of Chad a bit more. To his credit, when I told him what was going on and that I was sad about losing my grandma, and then also having to deal with losing a job on top of that, he was extremely nice and talked to me about it more than a lot of my close friends. Some might say it wasn’t genuine, that he had ulterior motives, but honestly, I really didn’t feel like he had an agenda for being nice to me when I was clearly going through a difficult time and just needed someone to talk to. It was such a huge juxtaposition between how he was being versus how the guy I had been dating for eight months had acted, and it was a very welcome feeling.

I already had plans to see some friends in Orlando while I was home with my family, which I mentioned to Chad, so he kindly offered to let me stay with him. I was excited, because I really needed to see my friends after everything that had happened recently, and I really thought that seeing them plus staying with him was exactly the kind of distraction I needed to feel better. He said he had a guest room, so I could totally stay with him, no problem, and he’d buy me a drink when I got there to make up for everything that had been going on lately. I remembered that one of my other friends from my internship who was friends with him had recently stayed with him when she went down and she didn’t have anything bad to say afterwards, so I figured if I could save some money and stay with someone I knew, and have some fun with it, why not?

My home park.
Photo by Benjamin Suter on Pexels.com

Except one thing. He didn’t have a guest room. I got to Orlando, saw a friend that day, had my drink with Chad, where we talked and caught up on everything that had been going on in our lives, talked about work, all that fun stuff, and then went back to his place. He had kissed me in the parking lot, so on the way, I was wondering how exactly this was going to work out if he’d planned for me to stay in a guest room. But, apparently, this was not something I had to worry about as I arrived at his place to find out that the “guest room” was really his couch. So, it was the couch or his bed. I could have stayed on the couch, where it turns out my friend had slept when she stayed with him, but considering the way we’d been talking recently, I’ll let you guess which one I chose.

Overall, we had a fun time. It definitely wasn’t anything serious, but I was still a little pissed when less than 48 hours later one of my friends from Orlando, Lizzie, texted me asking if I knew a guy from Disney named Chad and I said yes, why? They had just matched on Bumble and he’d asked her if she wanted to get a drink that night, and she saw we followed each other on Instagram so she wanted my advice. I told her about staying with him just that weekend and asked that she not go at least this time because it was not exactly going to lift my confidence for him to go on a date so soon after me being there. And, considering the hit she knew my ego had recently suffered because of The Cheater, and because girl code is REAL, she quickly obliged.

We still talked here and there and kept things friendly, and then the next time I was planning on going to Disney for a 10K, he invited me to stay with him. I wasn’t very tempted because I’d be going with my family and did not want to deal with the questions of where I was going from my brother, but I did think about it. I had already booked my tickets, but he kept trying to convince me to change my flights, but I am not about that change-fee life so I never did. Good thing, because he ended up having something going on the night I would have changed to arrive on, and he would have had to bail on me last minute. So that would have been $200 down the drain.

Then, when I got back to Boston, I saw on Instagram that there were some ~fishy~ things with him and another girl. Which is totally fine – he could do what he wants, I was doing my thing, too – but, I don’t think you should be trying to convince a girl to spend $200 to change her flight with whatever was going on with them happening. So, given that I was, frankly, VERY tired of dealing with bullshit from men, I told him off. I told him I didn’t appreciate being jerked around like that, and that it wasn’t cool to do whatever he’d been doing and that he needed to be honest from now on. He apologized, and things went back to being friendly. We ended up having a mini falling out a few months later over something that wasn’t really that serious, but I had a no-tolerance policy by that point so I was done. I blocked him everywhere.

However, after seeing his multiple attempts to contact me on my computer (side note, why won’t my computer block the same numbers that are blocked on my phone? Does anyone know how to fix this?) I finally decided to answer. We talked it out, he apologized again, and I told him that fuckboy is NOT a good look on him so to cut it out, and he agreed.

So, Chad, The Host, is one of the few guys on here that I still have contact with in some capacity, which also means that I allowed him to read this before it was posted and veto anything in here that he didn’t want disclosed and give me feedback on things he’d appreciate being changed. Honestly, this should be a lesson to men that if you own up to your mistakes and don’t turn into a major jerk, you’ll end up getting at least a slightly better edit on here than the rest of them. And my parting lesson to women? When a guy offers to let you stay with him for the weekend, make sure that he ACTUALLY has a guest room.