crazy dating Archives • Madeline Olsen

Chapter 18: The Love Square

After starting to work at Encore Boston Harbor, I realized that the pickings were VERY slim if I wanted to meet a guy there. Not that I was only working there to get a boyfriend, but I like to always have “convenience crushes” – someone that might not really catch my eye if I met them at a bar, but they at least motivate me to put a bit more effort into my appearance each day. I quickly realized that simply hoping that some young, attractive, rich Christian Grey type was going to need an in-room check in (and then fall in love with me) was going to have to be my “convenience crush” (despite feeling like an old lady in my awful-fitting skirt and blazer, I managed to look mostly good most days). However, it seems that there were quite a few guys working there who did not have the same problem I did in terms of finding a fellow employee to crush on, and that is how my Love Square fiasco happened.

There are three characters in this, besides me. The security guard, Tomas, Valet #1, Ricco, and Valet #2, Leo.

Tomas started it all. I met him at lunch one day when going on break with one of my friends, Carol, as the two of them were friends already. I didn’t think much of it other than that he was a friend of a friend, so we talked throughout lunch and overall, he seemed nice. Not my type, but again, I wasn’t thinking of him like that – I had already resorted to holding out for Christian Grey (minus the narcissism and emotional abuse) – so I just kept it friendly.

We ended up having lunch together a few more times, with Carol and/or other friends, and while he was nice, we just really did not have much in common. So, when a little bit later Carol told me that she knew someone who liked me, and was asking her about me, I didn’t expect it to be him. But, it was. He was asking if she knew if I had a boyfriend, and if she’d tell me that he liked me.

Now I don’t know about you, but I am NOT attracted to people who are too afraid to tell someone their feelings themselves. This isn’t middle school recess. But I figured he must be insecure, and I didn’t want to be mean. At the same time, though, having done the whole “work people knowing my personal life” thing, I was not too keen on him getting Carol involved. I didn’t want her to get further involved, so I told her I’d handle it.

I don’t remember how we had each other’s numbers, but we did, so I texted him and let’s just say that throughout our few brief texting conversations, I realized that there was really nothing for us to talk about. When he finally got up the nerve to ask me out, I told him I didn’t want to mix my professional life and my personal life (kind of true), so thanks, but no thanks. I thought that would be it. But it was not.

A little bit after that, I ended up at a volunteering event with Tomas and it was super awkward at first even though I tried to keep things friendly and chill. He was clearly still upset (again, not attractive) and it was becoming pretty obvious, to the point where I just tried to avoid him for the most part. I ended up meeting someone there who had just moved up from Florida who was really nice and offered me a ride home, and I could literally feel the death glare on the back of my head as I got in his car. When I told my new friend about it, he said it was pretty clear to him the whole time we were there that Tomas was jealous that I was talking to other guys. Not cool.

Around this same time, I began talking to Valets 1 and 2, Ricco and Leo, whenever I was outside waiting to do a meet and greet – or, more likely, just avoiding doing work that didn’t need to be done yet in the back office and taking one of my multiple laps of the day.

Leo was funny, I don’t really know how to describe him, but he’s just very much a harmless flirt I guess. Comes off a little bit cockier than he deserves to be, but overall not the worst person in the world. Plus, he always talked about how much he loves his family so I thought it was sweet.

Ricco, on the other hand, began to get on my nerves pretty quickly. You know those people who have to give you a lecture for every single thing you say? That’s Ricco. I could go outside and run into him and say something about needing to stop at the store to get milk on the way home, and he’d end up giving me a history lesson on the dairy industry. It was exhausting, and honestly, I usually ended up tuning him out shortly into our mostly one-sided conversations because I could barely get in one word and it would make me so angry that he didn’t realize how much he talks over people. He’s also younger than me, and it shows.

So, those are the players in this story. Now, onto the good stuff.

One day, I was sitting at my desk in the back office when one of my coworkers, Judy, came in and told me that there had been a guy out front asking about me. At first I thought maybe it was a guest (Christian Grey, is that you??), but then she told me that he works here. She said it was someone I’ve talked to before, because he said we had, and that he was asking her what she knew about me, and if I was seeing anyone, and that he had left me a note but she didn’t have it on her at the moment.

My mind immediately went to Tomas. At this point, it had been a little while since I had turned him down the first time, so I thought he was trying again but from a different angle. And let’s just say that I was PISSED.

I went on my lunch shortly after and vented about it to another of my friends, Amanda. While on lunch, I decided that I needed to say something to him. So I pulled out my phone and texted Tomas that I’d already told him no, and to stop asking about me, and that I don’t like him involving my coworkers because I’m a private person (lol), and basically, to leave me alone. It was pretty heated. He didn’t respond.

But then I got back from lunch, and I found something on my desk. It was a note, saying the writer thought I was beautiful and cool and wanted to know if I’d get coffee with him sometime? It was signed by Ric.

Immediately, I panicked. I realized I’d had the wrong person and I’d just gone off on Tomas for asking about me when it wasn’t even the right person going all middle school on me and my coworkers. I started to get up and find Judy when she walked back in and asked if I saw the note, and I said yes, and asked her if it really came from him. She replied, “Yes! It’s from Ricco, the valet! Everyone calls him Ric but his name is Ricco.” Now I REALLY knew I’d messed up, and the look on my face must have expressed that because she asked me what was wrong. I told her I’d texted the wrong person to yell at him and I needed to apologize.

First, I apologized to Tomas for yelling at him, but I don’t think he appreciated that I had to say, “It was someone else who likes me and was asking about me” and unintentionally rubbing it in that he wasn’t the only person who had a crush on me, and then I had to go outside and talk to Ricco. I gave him more or less the same spiel I’d given Tomas earlier, that I don’t mix personal and professional and I wasn’t interested.

Of course, when I was getting on the T that day to go home, who joined me? Ricco. And, he just made me even more sure that I’d done the right thing by continuing with the unwanted and unnecessary lectures about everything I said and continuing to hint that we should go out sometimes, despite me clearly saying, “no.”

This is where Leo comes in. After all of this, he was the lesser of the evils so if I went outside to the valet area, I’d try to talk to him to avoid Ricco. I also ran into him in the back hallways quite a bit. So, we’d developed a friendly rapport.

One day, we were talking and somehow he started doing some rapid-fire questioning, asking me things about myself, and at one point, he asked me out. Because of the quick-questioning, I impulsively said, “Yes.” I immediately regretted it because I knew it was going to start stuff, but at the same time, Leo didn’t drive me quite so crazy so I wasn’t completely opposed to getting a drink or something.

I really hoped that nobody else would find out, but he must have said something because for the next day or two, Ricco gave me some serious side eye and death glares whenever he saw me. Then, he got fired so I didn’t have to worry about it anymore. Tomas did come by my department every once in a while and still made it so obvious that he was mad at me for turning him down, so he’d ignore me which didn’t really bother me, but it was definitely weird considering we’re all adults.

I never did go out with Leo, we just never really followed up on making plans, and then I quit and we didn’t have any way to keep in touch. The funny thing is, I worked with some (actually, all) insanely gorgeous girls at Encore, so I have no idea why these three guys all were so focused on me. Other than my theory that kind of weird guys are attracted to me because they know I’m nice and think I’ll be too nice to turn them down, but then again I think Tomas and Ricco learned that is NOT the case with me.

So, that’s the story of my weird little work love square. I guess, technically, to really be a love “square” at least one of those guys had to be in love with another guy, but it sounded better that way. And, it’s my blog, I can call it what I want, right?

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.