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. 

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. 

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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. 

Chapter 8: The Bartender

Shortly before I eventually ended up leaving Orlando, I was going through a bit of a dry spell and decided to get my booty back on Tinder. I was looking for a reason to stay, or another reason to go, and figured that if nothing else, maybe Tinder would give me a good story to leave with. It did.

I matched with this guy, who I’ll call Diego because I honestly couldn’t even remember his name when I started writing this chapter (I did remember it later, though), who was a bartender at a place in Downtown Orlando. And let’s just say that he was VERY aggressive. Not in a gross way, just very upfront with his attraction to me and what he was looking for. And, I liked the attention. We matched not too long after I had officially cut off and blocked Christian and returned the sweatshirt I’d had for years to a mutual friend that ended up being collateral damage in the break-up, had my roommate sit with me while I shredded all the birthday cards and letters, and defriended anyone who was his friend. So, I was ready for something new to take my mind off of things. 

By the way, if you’re wondering what sparked my FINALLY ending that relationship, I said “no” to him coming over one night and then after he ignored me for three days, he finally told me that I wasn’t worth his time or his friendship if I wasn’t going to sleep with him anymore. Lovely, right?

Anyway, enough about him. Diego and I started talking, and he started asking me to come over to his place very quickly. But being the Law and Order: SVU lover that I am, I knew there was no way I was going over to some stranger’s home without meeting in person. So after talking for awhile and getting to know each other more, and starting to feel more comfortable with meeting in person, I kept feeling myself be more and more tempted to take him up on his offer, but ultimately the part of me that does not want to end up as the inspiration for an SVU episode kept winning out.

So finally, one day while I was at the mall and he was teasing me about not coming over yet, I  asked him what he was up to. He was at Best Buy. Perfect, I was at the mall not far from Best Buy. So I told him to stay there and I’d meet him in the parking lot. And that’s exactly what we did. 

He was a bit shorter than I expected, but cute. Very buff, and he had very nice eyes. He was very confident but didn’t seem to take himself too seriously, so it kind of balanced out. We talked for a bit, and I felt more comfortable around him having seen him face to face and getting a better feel for him. I told him that I would like to get tacos or something before hanging out alone, so we decided that at some point, that would eventually happen. But, I wasn’t planning on staying in Orlando for too long since I’d put in my two weeks, so I told him it would have to be sooner rather than later.

The night of my last day of working at Disney, one of my best friends invited me out with her boyfriend and some friends to a bar downtown where during certain hours, you paid $20 for all you could eat and all you could drink wine, beer, or their signature drink. Coincidentally, this was the same bar that Diego worked at, so I told him I’d be there that night. If you know anything about Orlando traffic, you won’t be surprised to learn that it took us about 45 minutes longer than expected to get there. So by the time we arrived, all the food was gone. Which meant that if I was still paying $20 to get in (which I think is ridiculous), I would be getting my money’s worth in drinks.

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This was a bad idea for many reasons. First of all, I’m a lightweight. I have one glass of wine and feel tipsy (despite my stories on here, I really don’t drink often so when I do, it hits me). Secondly, I hadn’t eaten dinner because I was expecting to eat there. And thirdly, because I knew the bartender – and he was desperately trying to get in my pants – the small cup given to me at the door when I handed over my $20 was quickly replaced by the larger cup he gave me and was most likely spiking with more alcoholic beverages than the Pinot Grigio and sangria I requested. So I went quite a bit harder than I anticipated.

My friends and I left and went to another place, where Diego began incessantly texting me telling me he was off work and could take me home if I wanted. Unfortunately for him, no matter how much I’ve had to drink I always know how to take care of myself and keep my head about me, so I knew going home with someone I’d only met once when I was in that state was not a good idea. I was also too busy throwing up straight liquid at this bar (once on my friend, I’m still so sorry about that) to respond to him right away so he eventually got tired of waiting for me and left on his own.

The next morning, I texted him to apologize for not responding and told him I hadn’t been feeling well so my friend’s boyfriend (our Designated Driver) had driven me home with them and dropped me off late, where I went right to bed. I was finishing up moving out that day before my family came up for a quick visit, so I pretty much knew it was never going to happen. Considering he got pissy when I told him that no, going home with someone I don’t know well when extremely drunk does NOT sound like my idea of fun, that was more than okay with me. We followed each other on Instagram for a bit before I did my next purge, and that was the last I ever saw or heard from The Bartender. 

Chapter 6: The Vegan

When I first moved back to Orlando permanently a year after I graduated college, I got a job working Front Desk at a brand-new resort opening up at Universal Studios. It was really exciting getting to be part of the opening team for such a cool place, and I was lucky enough to work with a lot of amazing people. 

The majority of the other Front Desk representatives were like me – mostly female, early to mid 20s – but there were a few guys. While they were great, but without giving away too many details of people I really liked, let’s just say for some reason or another, it wasn’t going to work with any of them. Not that I took this job expecting to meet a guy, nor was I necessarily looking for one at that point in my life, but it would have been nice to have someone to look cute for besides the creepy guys coming in for conferences and taking off their wedding rings so they could hit on you and your friends as they checked in, you know? 

But apparently there was someone in the resort. His name was Dylan, and he was just a little bit older than me. He was tall, had dark hair, a nice smile, and worked in IT. He was friends with one of my supervisors, and would come by to say hi to her, especially later at night when things were quiet, which is how we eventually met. We started talking, and quickly learned we had a similar sense of humor and he just seemed like a genuinely nice guy. So of course, I developed a crush. 

The one and only flaw was that he was a vegan – I have nothing against vegans, and I myself have tried out veganism a few times  – but for some reason all I could think about was, “What if we’re out doing something and I get hangry (very likely scenario) and we can’t find anywhere he can eat, and I just want a cheeseburger?” I know this sounds silly, but to be fair I have self-destructive tendencies that were running rampant at this time due to the situation I was in with he-who-shall-not-be-named (he was giving me a three and a half month long silent treatment because I dared to call him out on being a hypocrite about something), so having a nice guy who actually had his shit together was sending warning bells to me that this guy could REALLY hurt me if he wanted to, leading me to go, “SELF DESTRUCT, SELF DESTRUCT” and finding the one bad thing I could to keep him at an arm’s distance. I also just really like cheeseburgers, okay? 

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If I’m remembering correctly, one night, he came over to say hi to his friend, my supervisor, and was talking about something cool he’d seen on the other side of the hotel as he walked over. It sounded like something I’d be interested in, so she said I could walk over with him so he could show me. When we got over there, he admitted that there wasn’t actually anything over there, he just wanted to get me alone so he could ask me out and ask for my number, which was pretty cute. Now that I think about it, to this day I think he’s the only guy who asked me out in person and not via text. 

We made plans to go to Halloween Horror Nights later that week, and I was feeling pretty flattered, honestly. Like I said earlier, there were not a lot of eligible bachelors for us young-20s single ladies, so once Dylan made an appearance in our office I knew that a few other girls had a bit of a crush on him. So, it was pretty nice to know that I was the one he wanted to ask out when I knew of at least a few other girls that had their eye on him. It was just a nice little confidence boost.

We went to Halloween Horror Nights, and oh my gosh, even now I still feel bad for what I put him through. I love being scared, but I am THE biggest scaredy-cat. The first time I went to it was with my family, and I screamed so much in the first house we went in that immediately afterwards my parents walked me over to one of the bar carts and bought me a drink to get me to chill out. The first house he and I went in was called Tomb of the Ancients and I started getting scared while we were still in line. He went in first, and I basically squeezed the life out of his hand and screamed into his neck the entire time. This went on throughout every house we went in. But, we had a great time. We said good night, and made tentative plans to hang out again. The fact that he was still interested in me after I screamed bloody murder for three hours is impressive, honestly.

We talked for a few more days, and then he asked if I wanted to go to lunch with him soon and I said yes. I figured we would go somewhere in the general vicinity of where we worked, not realizing where he lived was further away, so when I Googled the place he suggested and realized how far out of my way it was I FREAKED. To this day, I have no idea why I reacted the way I did but if I had to guess, it would be because I’m too fucked up for anyone to love. Just kidding, that’s what Adam would have said, but that’s not true.

Honestly, I think a part of it was me starting to realize that I had been very badly controlled by The Narcissist and so much of our relationship was me going out of my way for him and never being met in the middle, so when this guy that I really liked made an innocent suggestion to go to a place he liked, not realizing it was further from me than I felt comfortable traveling, I thought he was trying to control me and have me make all the effort, too, and I didn’t want to end up in that situation again. I also didn’t know how to have a disagreement without it leading to a fight, so I was immediately on the defense. That and, you know, those lovely self-destructive tendencies (side note, shout out to my therapists for helping me work through that and to not be so self-destructive anymore). So I panicked, and I lashed out. 

After that totally random argument, we never spoke again. At this point, I had perfectly timed putting in my two weeks notice for right before my best friend from high school, Amanda, came to visit me because I already had the week approved off, then I had a few more morning shifts and was done. I still feel bad for how I acted towards him, and sometimes I think about apologizing (I still have his number because iCloud never lets me delete numbers) but I feel like it’s been at that awkward amount of time where while I finally realize why I reacted the way I did, it’s also been almost four years – so is it really even worth it to say I’m sorry for acting like a bitch out of nowhere, or is that just weird? I think it’s weird, right?

Who knows what would have happened if I hadn’t freaked out at the restaurant suggestion. But I like to think that things happen for a reason, and if it was meant to be it would have worked out some way. I do think people come into your life for a reason, and even though this was the one situation where I can (and do) 100% take responsibility for it ending, I’m glad it happened. I think that because of him, I learned that it’s not just assholes who will like me – nice guys like me, too. That I was allowed to date other guys when you-know-who was doing who-knows-what with other girls, and that I should not, under any circumstance, feel guilty for it. Because he really was (and I’m sure still is) a great guy – even if he is a vegan. 

Chapter 5: The Dolphin Trainer

You know how in movies people always come up with a code word before a first date, so that if it completely sucks their friend can call with “an emergency” to help get them out of it? Well, that happened to me. 

Ash and I met through a mutual friend. A friend I made shortly after moving to Orlando, I’ll call him Cornelius, introduced me to his friend group, and we frequently hung out together within this group – dinners, escape rooms, movies, house parties, Halloween Horror Nights… you get it. He was a really nice guy, not what I thought of as my usual “type,” but I liked talking to him. He was funny, smart, seemed like a good friend to everyone in the group, and worked as a dolphin trainer at a certain well-known ocean focused theme park in Orlando. 

I don’t really remember how or when this happened, but eventually, Ash asked me out. The funny thing is that later on I found out through another friend in our little group that one guy was trying to find the right time to ask me out, but then someone else told him he thought I had a boyfriend (I didn’t) so he never did. So then Ash swooped in. Whoops. I wasn’t sure that I was really looking for anything at the time, but I figured, I’m trying to break my walls down, I need to meet more guys, he’s nice, and I’ve only ever hung out with him in group settings – I’ll give him a chance, what do I have to lose?

We met for dinner in Downtown Celebration (which is super cute, by the way). We got Chinese food, he paid, which was very polite and gentlemanly of him. We had a really good talk, it was nice to get to know him one-on-one versus the group interactions we’d had so far. I remember at one point he told me that he felt like I see the world very differently from most people, and that it’s interesting to hear me talk the way I do. In my head this makes me think like I sound like some sort of wise Buddha, but I could be wrong. Either way, I’ll never forget that. It’s still one of my favorite compliments I’ve ever received. 

After dinner, we walked around downtown for awhile before deciding to get some ice cream. He has a really severe allergy, so I don’t even remember if he was able to even get any but I was hardcore craving Kilwin’s, and he obliged. Then, we sat on a bench by the water to talk some more.

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We’d been talking for awhile, but it still didn’t feel like “that moment” where you know the date is about to end so you need to start wrapping things up and making plans for next time and all that. Which is why I’m still not sure why he decided to take that moment to say that he was having a good time, and did I want to go out with him again?

I panicked. I HATE turning people down. I’m that person who texts people I don’t click with after a first date to tell them, “I just didn’t feel that spark I’m looking for, but best of luck – you’re a great guy!” I refuse to ghost people, and I hate having to reject people. I knew Ash was nice, but “I just didn’t feel that spark I was looking for,” so I knew I had to tell him that. So, I told him no. “But not a hard no, a soft no,” is actually what I said. Which then I had to clarify as not meaning to ask me out again at a later date, but that we could still hang out in a group, just not one-on-one. Then I swiftly changed the subject.

Not even five minutes later, Ash got a call. I could hear panic in his voice, something was wrong. It sounded like someone, or something, was sick. He hung up and told me that there’s a dolphin at work that’s been sick lately and she just took a turn for the worse, and he has to go now because this might be his only chance to say goodbye. In my head I was thinking, this is a bit fishy (get it?), but being the nice person I am, I go with it. I like to believe the best about everyone and everything. I told him to run and that I hoped the dolphin was okay, so he said goodbye and ran off to his car. I left a little bit later.

Later that night, I got a call from him apologizing for running off. I ask how the dolphin is – she’s doing okay, they’re optimistic – we had some friendly chit chat for a bit, then we hung up. I never told anyone in our friend group about this, I didn’t think they had any reason to know we went out once, so we just acted normally next time we saw each other. It was a little awkward at first, but we got through it. I’m pretty sure he went out with someone else in our friend group shortly after, which was great for me because it meant less pressure and guilt.

Months later, I was talking to Cornelius about funny dating stories and I finally told him about my date with Ash, and he said, “Oh, yeah, I knew about that.” So I asked him if he knew that it ended when Ash had to go check on a sick dolphin, and he burst out laughing, asking me if I really believed that was a real phone call. That’s when I found out that the call about the “sick and possibly dying dolphin” was actually from Cornelius, thanks to an SOS text message he’d been sent by Ash to get him out of the awkwardness of me refusing a second date. My naiveté knows no limits sometimes.

So, that’s The Dolphin Trainer. Honestly, I think it’s pretty hilarious that I actually believed that, and I still think Ash is a good guy (if you’re reading this, no hard feelings!), but the fact that I actually had someone use an SOS text/emergency call on me is pretty classic. Especially since I’m pretty sure I’m the only person in the world whose emergency call involved a fake dolphin story. There’s a first time for everything, right? I just hope that was the only time someone has had to use that call on me.