My sugar daddy gave me over £12,000 then completely broke my heart

I was sitting in his kitchen, crying, holding a brown paper bag with $16,008 (around £12,500) inside.

The man who had just given me this sweet stack of cash had also, coincidentally, just broken my heart.

In the summer of 2022, I decided to peruse the virtual aisles of a website that matched sugar babies in need with a sugar daddy counterpart.

I had tried it once, years before. I went on one date with a man who talked about jazz the entire evening and was very eager to get to bed with me. The whole thing didn’t sit right, so I pocketed the $50 he had given me and ghosted him. 

But now, I was feeling risky – and I was broke – so I tried again.

The biographies on this site are a lot more straightforward than your typical dating apps.

Some list kinks, some outline the terms of the desired ‘arrangement’: ‘Lonely tech guy with astigmatism seeking out girl to cuddle and speak in baby voice – come over tonight for $200’. 

Eventually, I stumbled upon a profile that seemed oddly sweet. ‘First time on here,’ it read. ‘You don’t have to be good-looking, just please be kind’.

I liked what I saw – so I sent him a message.

We talked about being native New Yorkers. He kept saying, ‘Don’t worry, I’m normal’, coupled with some sort of self-effacing comment, like ‘I’m normal, if you don’t mind an older guy with thin hair.’

I could tell he was funny, and I felt he was genuine. 

We chatted for two weeks on the site, which led to a two-hour phone call, and then to our first date at a café in Manhattan’s East Village. 

Salvatore*, or Sal, was a real Italian-American, born and raised on Staten Island. His parents had both come over from Sicily and he worked in the family construction business.

I arrived early, in a dress; Sal walked in, hair frizzy, wearing a worn green raincoat. He looked like a normal guy, no pretenses. Just looking at him, I felt at ease. I gave him a very nervous kiss on the cheek. 

Over the course of our date, I learned a few things: Sal was funny, he was weird, he had an insane work schedule, he was self-deprecating (especially about his looks, although he wasn’t a bad-looking guy), he was a full-time caretaker for his mother, and he was rich. You wouldn’t know it to look at him, however, because he dressed like he had lost his luggage on an international flight.

‘I used to have nothing, now I’m very comfortable,’ he said. ‘I like helping people out.’ The way he talked about money was relatable, not intimidating. I felt like this guy wanted to give me money, but, moreover, wanted to help me.

We got along very well. Sal asked a little about me –  then we got to talking about the arrangement. ‘What do you need?’ he asked me.

I replied that I was a comedian who wanted to focus full-time on her craft, and I needed enough money to cover my rent and utilities. ‘Like $1,800 a month?’

‘We can do that,’ he shrugged casually.

‘So what are you looking for?’ I asked him in return.

‘Ehh… I want someone who feels like my girlfriend without the responsibility of time or commitment. And I want to have sex. It’s been many years.’

We agreed we would see how things went. Then he handed me a small white envelope and said: ‘You seemed like a nice person, so I wanted to give you something, in case I never saw you again.’

When I left the café, I opened the envelope. $1000 fell out. Holy s**t, I thought. Even if this arrangement didn’t go anywhere, this was still pretty awesome.

Sal’s schedule was such that I didn’t see him again until two months later. And that’s how it was for the entirety of our relationship: one dinner date downtown, $2,016 (‘I got a weird thing with numbers,’ he said, ‘it’s my OCD’); three months later, a date on Staten Island and $1,878. 

The money and meetups were unpredictable, but the conversation was electric. I connected with him. We made each other laugh.

At the beginning of our relationship, the idea of sleeping with Sal was like, all right, I’ve f**ked worse for less. But by the six month mark, not only did I really like him, I actually wanted to f**k him. I liked his personality! What a novelty! 

Most of the relationships I’d had before were affairs with men who wanted me to be the revitalisation in the marriage that was dissolving before their eyes. Sal was a nice shy guy, a little self-effacing goofball.

But by the six month mark, we had only just had our first kiss. 

In July of 2023, 10 months into seeing each other, he finally asked me over to his place. This is it, I thought. 

‘Come here, come to the kitchen,’ he said, almost as soon as I walked in. He pulled out two stools and a wrinkled brown paper lunch bag.

‘I want you to have this,’ he said, as he handed it to me. ‘It’s $16,008.’

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‘I feel like… I feel like you’re pushing me away,’ I said. Which is a strange thing to say when someone hands you $16,008.

‘You’re not wrong,’ he sighed. ‘The truth is, I started talking to someone else. I met her in a bar. She’s younger than you. I started to fall for her. And then I thought about you and me. And I thought to myself: What am I doing? If I want a relationship, it’s gotta be organic. I want to feel like you want to see me, not like you’re obligated to see me.’

‘Sal. I like you,’ I pleaded with him. ‘I care about you. And, if we actually dated, I’d probably fall in love with you, and you wouldn’t believe me. You’d break my heart.’

‘That’s fair.’ He looked away from me and pursed his lips into a sad smile. 

He reassured me that he’d always be there if I really needed him. I asked to kiss him one last time, and told him I really cared for him.

I couldn’t do anything but respect his feelings and his desire for a real connection.

It was hard not to talk to him, not to look forward to our late-night chats, making each other laugh. I texted him a few times here and there, wishing him Happy Christmas. 

This all happened in 2023. Sal’s money was the reason I was able to pay my rent that year. The reason I was able to afford treatment for my cat’s cancer, the reason I was able to take myself and two friends to the Edinburgh Fringe Festival, the reason I could buy gifts for my family for Christmas.

Sal has given me more than just money, though. He is also the reason I’m going (back) to the Fringe this year – my strange story with him is at the centre of my new musical comedy show, The Day My Sugar Daddy Dumped Me.

Because, since seeing Sal, I’ve broken the habit of boning down old geezers. The show is the in-depth story of how Sal and I helped each other heal… with a lot of my past debauchery in between, including, but not limited to, a rap about the clitoris.

When Sal gave me the money two years ago, he told me: ‘You’re gonna forget about me, OK? You deserve to fly, and I’m only gonna hold you back.’

Now, I’m about to fly to Edinburgh for the second time.

I’m so happy that I never forced anything between Sal and me. It was an incredibly meaningful relationship to me, as strange as the circumstances were. It was the first time I’d developed feelings for someone – not through sex or the thrill of infidelity, not because a man looked at me and saw his youth – because of how I got to know him, how we got to know each other.

Every so often, I’ll come across a construction site with his last name on it. And, when I do, I get so tempted to call him, text him, see him.

But I don’t.

I let the thought sit and simmer, and I smile.

*Name has been changed

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