Dating a Trust Fund Baby:
He tried to use Trump Tower to bribe me for sex. As if.

Back in the day when I was seriously single and willing to date almost anyone, my friend set me up with a guy she knew. I was in my early twenties and he was almost forty but—and this is going to sound really shallow—he was semi-cute, rich, and I thought it could be fun. All I knew was that his parents had serious money, he had an outgoing personality, and my (so-called) friend described him as a “great guy.”

He was also known as a Trust Fund Baby.

His mirror selfies on social media showed a bathroom that was bigger than my entire studio apartment. I was intrigued. Can you blame me? I’d been used to dating boys who thought a romantic night was watching Seinfeld in their cave-like apartments that they shared with a constant stream of rotating roommates.

For the sake of this Trust Fund Baby’s identity, let’s just call him TFB. Also, let’s get one thing clear: This story is going to make me look pretty clueless too, but if I’m going to tell it, I’m going to tell it honestly. I mean, whatever. I know better now.

At first he seemed promising. He made actual dinner reservations at an expensive restaurant and sent an Uber Black to pick me up. I can’t remember exactly what I wore but I know that I was dressed well enough to be seen at such an upscale trattoria as the one we were going to; definitely heels and something leopard.

He texted me while I was in the car.

TFB: “Do you like basketball?”
Me: “Yeah, for sure.”
TFB: “Okay great. New plans. Will fill you in when you get here.”

This would come to be known as my first mistake. Although, I couldn’t have known it would be a mistake to admit—honestly—that I like basketball. But that was the moment our reservation at the swanky restaurant was cancelled. We ended up going to a nearby pub. Of course, there were flatscreens mounted above the bar so we could catch every second of the Raptor’s game.

At the risk of sounding extremely judgmental, I hated his outfit. He was wearing a turquoise cotton polo shirt with checkered cargo shorts and leather moccasin-style loafers. Secretly, I hoped that he had changed into something more casual when he decided to take me to the pub. His outfit looked straight out of an Abercrombie & Fitch catalogue while his body looked more like a soccer dad—minus the children, as far as I knew.

Conversation was flowing (although he did most of the talking) and so were the drinks. I had two glasses of cool, crisp white wine with the meal and then a lemon drop martini for dessert—along with a slice of whatever cheesecake they had available. He was knocking back beers like nobody’s business, so I didn’t feel awkward consuming yet another martini.

The alcohol started to hit me and we decided to wrap things up.

As we were putting on our coats and heading out the door, he got a text from one of his friends telling him to come out for drinks. He asked me if I wanted to come and I politely declined. Then, he started begging me: “Please? Come on! Just one more drink. I promise, just one and then I’ll get you a cab home. Okay?”

I caved. I guess I liked the idea of him wanting me around? Who knows.

However, after one glass of champagne, I started to seriously feel the alcohol and he started to seriously feel me up. His grubby (and a bit chubby) paws were all over me and I knew I had to get out of there. I told him I was leaving. Again, he tried to get me to stay but I told him I was actually leaving. He begrudgingly called me an Uber, but stayed behind, drank, and sulked. Or so I imagine.

I know you’re probably thinking that our first date doesn’t sound unbearably horrific. It’s just a run of the mill bad date. Everyone has those! Well, you’re absolutely wrong. Just wait.

The real drama went down on our second—and final—date. I could tell he wasn’t my type after our first encounter but he was extremely persistent in asking me out a second time. Everyone deserves a second chance. Right? Maybe not.

Again, he sent a car to pick me up and take me to the restaurant. This time he was dressed better; he wore a dark suit with a pink button-down dress shirt and leather loafers. He kissed me on the cheek when I got there—which was an improvement from him attempting to shove his tongue down my throat the last time I saw him.

We got a table for two and almost immediately after we sat down he asked me if I was going to go home with him afterwards. Excuse me?

TFB: “We’ve been out twice now. Are you spending the night with me?”
Me: “Probably not. We literally just started this date.”
TFB: “Why? Women want me.”

Then our waitress came over. She was pretty, petite, and blonde. TFB was extremely flirtatious as we ordered an appetizer and two French 75s. I was annoyed, but I thought I’d just try and enjoy the night since I had gotten dressed up and I wasn’t about to waste my YSL make-up on a date gone wrong. (Little did I know.)

We got to talking about other things but somehow it kept coming back to if I was going to sleep with him after dinner.

TFB: “Seriously. Why won’t you come over?”
Me: “Because I’m not doing that after the second date and I have to work tomorrow.”
TFB: “So it’s about work? I’ll pay you double. Just call in sick.”
Me: “No, thanks. I’m good.”
TFB: “I’ll pay your wages and I’ll book us the presidential suite at Trump Tower. You can spend all day tomorrow at the spa. We don’t even have to have sex, just spend the night with me. I promise.”

Yeah, right. First of all, the fact that he thought I’d be interested in Trump Tower is atrocious. But that’s besides the point. Second, I was not buying the “no sex, just sleep” act. What a joke.

I finished my drink and changed the subject.

Before I knew it, he excused himself to go order another round. I was relieved that he was leaving me alone at the table for a few minutes… until I turned around and saw him chatting up the server. Like, aggressively chatting her up. To be fair, they were too far away for me to tell what they were talking about. However, I soon found out.

He actually had the nerve to ask her for her phone number, just to prove to me that women find him attractive and want him. (Those were his exact words.) Even though I didn’t find him overly desirable, I still didn’t want him disrespecting me on a date by asking for another woman’s phone number. Hypocritical, maybe, but honest.

TFB: “She gave me her number. She’s all over me but I just want you.”
Me: “You’re an asshole.”
TFB: “I was just trying to prove a point.”
Me: “You know what? Thanks for nothing. I’m leaving.”

And with that, I grabbed my jacket, my purse, and I stormed away from the table. I had just barely made it to the exit when I felt him grab my arm and spin me around. It was like a movie: girl makes a dramatic exit, boy chases her, they kiss and make up. (Not.) I hate causing a scene.

TFB: “I’m really sorry. I know what I did was wrong. Look, she just brought us our drinks. Please just have this one last drink with me and then I’ll take you home.”

For some reason unbeknownst to me, I agreed. I let him lead me back to the table. I sat there with my coat on, rapidly gulping my champagne cocktail while he tried to apologize, again and again. It took all of ten minutes to finish our drinks and get the bill. (He paid.)

I was pissed off and just wanted to get home. He called a car and I was expecting to ride solo, but he jumped in at the last minute.

TFB: “You mind if I come along? I’m going that direction anyway.”
Me: “Sure.”

It kind of felt like that episode of Sex and the City when Charlotte won’t sleep with Capote Duncan (Toxic Bachelor) and so he calls her a cab and hops in to get to another bar—where he ends up hooking up with Samantha. Except the other “bar” that TFB was hoping to get into was my bedroom.

Once again, he started asking me if he could come over. I said no. He asked why. I said that I just didn’t want him to. Then he started completely freaking out—and I mean freaking out. Here was a grown-ass man, having a temper tantrum in the back of an Uber because I refused to have sex with him.

Trust Fund Baby: “Why do you keep saying no? Girls never say no to me! I can have any girl I want. Don’t you care that I want you?”

He then asked the driver to pull the car over. He told me to get out and find my own way home. I said I was more than happy to, unbuckled my seat belt, opened the door, and started to leave. He reached over and grabbed my arm once again, pulling me back in.

TFB: “What are you doing? Get back in the car. I don’t understand you! You should be begging me to stay in the car right now. Why aren’t you begging me???”

Honestly, I pitied him in that moment. He had been so spoiled his whole life and had zero concept of the word “no.” It was almost fascinating watching him. Here was a nearly middle-aged man, having a meltdown because he was refused sex. By someone who didn’t want him. It was sad.

My triumphant moment was wrenching myself out of his grip, getting out of the car, and never looking back.

Needless to say, I never saw him again—and I no longer speak to the “friend” who set me up with him either. Although our friendship didn’t end because of the horrible set up, but because of an avalanche of other issues and no one needs that kind of negative energy around.

Trust Fund Baby tried to text me a few times after our second date, but I deleted his number and blocked him on every form of social media. He wanted to go out a third time. Can you believe it?

—ᴍᴍᴍ