That Time I Dated the Trust Fund Charmer

Let me tell you about my experience dating the Trust Fund Charmer.

I had lived in Miami for 2 weeks when a guy sent me a message on OKCupid who seemed really cool. I messaged him back and told him he could only take me on a date if he promised to take me to see alligators. Yes, I like weird dates. Judge me.

So on a Friday he said he could pick me up but when I saw a giant black jeep with tinted windows in front of my building I refused to get in for a while because he could kill me in that thing without anyone noticing.

He laughed when I told him this.

“I’m serious” I said.

He swore he wouldn’t kill me (and I already left a note on my counter with his name and phone number in case I went missing and the police searched my apartment) so I got in. But first I made him tell me his entire name and searched for him on the Sex Offender Registry in front of him. For real.  

He took me to the Everglades to find alligators and when I saw some in the water I started throwing mini Oreos at them to lure them to me since my good looks obviously weren’t doing the trick. I got a little hungry too, so I started doing the “one for me, one for you” deal with the alligators. They didn’t seem to mind sharing. As they kept getting closer I was super excited, then suddenly I was super scared when I realized I’m cripple and can’t outrun these giant reptiles if they decide that the Oreos are not as satisfying as my flesh.  I immediately pushed the Trust Fund Charmer in front of me and hauled ass back to his giant deathmobile. Then he tells me it’s illegal to feed alligators in Florida. Umm, thanks for the heads up.

This guy especially loved Oreos!

During our outing he told me that he was a phlebotomist. After I gave him a confused look he explained what a phlebotomist is (they’re people that take blood). Then he took me to dinner in Miami and asked me what else I wanted to do. I told him I wanted to see Miami, so he drove me all around Miami showing me the different neighborhoods. Then he stopped at Walgreens to grab a drink and he came back with coconut cookies and a giant bag of gummy bears for me and I probably would have married him right then and there for that, so we kept dating.

The next Friday morning I told him in passing that I wanted to see a dolphin. He told me that in Marco Island his family had a beach house and you could see dolphins in the water every day.

“I NEED TO GO!” I squealed like an overly excited prepubescent girl.

“Let’s go tonight after work” he told me.

Go to an island with a guy I’ve known for a week?  Obviously I agreed because, well, dolphins.

When we got to Marco we were driving through a neighborhood and all I saw were giant mansions.

“This is a vacation place? No one lives in these houses full time?” I asked.

“No, these are mostly just vacation houses. Very few people actually live in Marco” he told me.

So then I start ranting:

“No way! These houses are huge! This is so wasteful! At least ten families could live in these houses but they’re just sitting there empty?!”

As I continue my rant he suddenly pulls up to a mansion that is so much bigger than every other house I was ranting about.

“Stop it,” I told him. “You’re not funny, get out of this driveway before someone sees you. Let’s just go to your beach house.”

But then he got out of the car, went to the door, and unlocked it. I felt like a massive douche.

I refused to go in for a solid 20 minutes because I still felt like he was joking somehow. He wasn’t.

When I went in this house I was silent. I’ve never seen ANYTHING so big. You could take every house and apartment I’ve ever lived in in my entire life and put them in this house and still have room for more. Then he pressed some buttons and the walls rolled up like some futuristic star trek shit and there was a view of an incredible pool that overlooked the ocean.

SHUT THE FUCK UP. THIS IS NOT REAL.

It was.

Evidence that this was real.

At that point I said, “I think you’re lying. You’re not a fucking phlebotomist.”

That’s when he fessed up and told me that he did take blood, sometimes, since he worked at blood bank... THAT HIS MOM OWNED. I’d say that’s slightly different than being a phlebotomist. Just saying. 

Anyway, I kept dating him, but we had some differences that we just couldn’t understand about each other.

He couldn’t understand why I would give my leftover steak to homeless people we passed on the street and I couldn’t understand why he didn’t give to people or good causes at all. He couldn’t understand why I would work so hard to defend the rights of people with disabilities and I couldn’t understand how he could take weeks off of work at a time to go on motorcycle trips and other vacations with his friends. He couldn’t understand why I would flip a shit on him every time he said “retard” and I couldn’t understand why he didn’t learn the first 50 times I explained to him why that was offensive.  

Despite all of this I continued to date him because I just moved here, I had literally ZERO friends except him, and he was the only thing that made me feel less alone in Miami.

Then one night I hit my breaking point. His friends were over and wanted to “eat a sandwich” (HIMYM fans can enjoy that reference!).  I told him I wasn’t going to judge him for it but it wasn’t my thing, so I would just go home for the night if that’s what he wanted to do. He said he was just going to go outside to tell his friends that he wouldn’t be joining them. Then he just went ahead and ate a sandwich anyway! Literally right outside where he KNEW I could hear him!

Ted & Marshall Enjoy a Big Sandwich.

I thought that was more than a little rude, so I packed up my shit and left. This clearly should have been the end, but obviously it wasn’t because, hi, have you met me? Nothing ends how it should in my world.

We eventually make up and do the apology thing, but then he stops responding to my texts and answering my calls, so I told him that if he was still upset that was fine, but I wasn’t going to play games, so I wanted to get all my stuff and be done. Then he tells me I’m being ridiculous and he can’t handle how much of a “roller coaster” I am and just blatantly ignores me.

IGNORES ME!

You want my attention? Just make it clear that you’re ignoring me. Logical, I know.

After he ignores me for a week I decide that I clearly need to make a grand gesture because, I mean, it works for guys in the movies. Why can’t girls be cute and make grand gestures too?

But of course I can’t do anything normally, so rather than doing something typical like, you know, standing outside of his mansion with a boombox blasting over my head, I decide that I should buy a bunch of fruit, draw sad faces on all of the fruit, and put them on his car while he was at work.

Because what says “Sorry, you’re clearly in the wrong but I’m pathetic and have no friends so let’s talk again” like a frowning pineapple on the hood of your car?  

NOTHING. THAT’S WHAT.

Guess what. It turns out guys don’t actually like grand gestures. In fact, his exact words were “you’re freaking me out.”

You don’t like my sad limes all over your deathmobile? Then I don’t like you.

And that is how my month long “relationship” with the Trust Fund Charmer ended. An unappreciated grand gesture that made him think I’m a serial killer.

And that’s also why I will NEVER do a grand gesture for ANY man EVER again.

Abridged Version:

Met a guy. He took me to find alligators. Thought he was a regular guy. Then he took me to his mansion beach house.  Turned out to be a Trust Fund baby who barely worked because he was too busy going on vacations. Got in a fight. He started ignoring me which pissed me off so I went to the extremes to get his attention (because I was super lonely and had no friends in Miami) so I tried to make a grand gesture by drawing frowny faces on a bunch of fruit and put them on his car. He thought I was a serial killer after that. I thought he was an unappreciative jerk.

Lessons Learned:

1. Always make friends in a new city before dating anyone.

2. Phlebotomists are people who take blood.

3. Sad fruit is hilarious and adorable, but clearly some people are terrible humans and don’t appreciate sad fruit on their cars.