I never expected my one-night stand to pursue me after our casual fling – Bundlezy

I never expected my one-night stand to pursue me after our casual fling

Jamie Valentino - I went on a first date with someone - except we slept together two months before
Our paths had first crossed as two anonymous torsos among many (Picture: Jamie Valentino)

On our first date, John* hit every possible green flag like my attraction was a video game he’d already mastered. 

For starters, he picked me up before dinner, was easy to talk to or sit in silence with, and focused on every word that came out of my mouth in a way that made me want to kiss him. 

The thing is, I’d already done the latter with him – and then some. Five months earlier, to be exact.

Our paths had first crossed as two anonymous torsos among many on Grindr in December 2024.

On a fateful Christmas evening, John and I made plans to hook up. The online conversation was brief because our nudes did most of the talking.

He was lucky because my family and I had stopped celebrating the holidays so I was home alone, while he was going to sneak away from visiting his mother. 

Jamie Valentino looking over his shoulder and smiling, with mountains and trees in the background
Although John and I had a nice connection, I didn’t expect our chemistry to snowball into anything (Picture: Jamie Valentino)

After the deed was done, he stayed for a couple of hours before he went back home. Although John and I had a nice connection, I didn’t expect our chemistry to snowball into anything significant after he left my flat, especially because he was just visiting town from Los Angeles

Unexpectedly, John followed me on Instagram the next day.

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For a moment, I considered leaving him as just another ghost of hookups past. He’d be one of the lucky men who’d had my body and now lived silently among the viewers of my Stories. 

But for whatever reason — call it love at first lust — I followed him back.  

John spent the next few months proving to me that silence wasn’t his MO – he praised the articles I shared and replied with horny emojis to my gym selfies. He wasn’t jaded at all, just a man who knew what he wanted and wasn’t afraid to show his fondness, even when I played it cool. 

Jamie Valentino - Having threesomes helped me get over my crippling jealousy
I considered leaving him as just another ghost of hookups past (Picture: Jamie Valentino)

While Instagram might encourage us to live as absent spectators in our friends’ lives, it allowed John and I to learn enough about each other to form a deep connection that might not have been possible otherwise. 

Deep enough, at least, that John messaged five months after first meeting to say he was returning to take me on a formal date

By this point, I had merely been responding to all his messages while he took more initiative to sustain communication.

I was intrigued by the invitation. 

John took me to which was his favourite restaurant, and the waitress immediately perked up when she saw him. A good sign. 

We sat side by side in a booth, and things took a turn when I started to tap into feelings for him I didn’t even know I had.

Even though we couldn’t be more different on paper (he has a kid, is older than I am, and works in Hollywood, while I’m tied to my family’s business in construction), none of it felt like a problem except living in different cities.

TTI - Jamie Valentino - I'm not being ignorant listening to music while talking to you - it helps my anxiety
I didn’t expect to fall for him until we went out together on our first date (Picture: Jamie Valentino)

Our effortless banter made me think about all the effort we’d need to put in to make a long-distance relationship work. My feelings caught me off guard, which raised the stakes exponentially since our first rendezvous.

In fact, I didn’t want to ‘like, like’ someone who didn’t ‘like, like’ me back. He had let slip that he was actually visiting town for a funeral, and I worried I was just an easy lay in his itinerary. It was at that moment that I decided not to sleep with him. 

Ghost me after a one-night stand? I wouldn’t notice. But ghost me after I’ve imagined a beautiful future together in my head? Shame on you. 

It was during dinner that he said: ‘You treated me like you just wanted a quickie. I was actually trying to get to know you.’ I countered that most people aren’t exactly thinking about learning someone’s life story on a hookup app.

He asked if I wanted to take a walk by the lake after dinner, which is when we had a passionate makeout on the pier, then he drove me home. It made me laugh because we kissed with such giddiness as if we hadn’t already seen each other naked.

So, How Did It Go?

So, How Did It Go? is a weekly Metro.co.uk series that will make you cringe with second-hand embarrassment or ooze with jealousy as people share their worst and best date stories.

Want to spill the beans about your own awkward encounter or love story? Contact jess.austin@metro.co.uk

Jamie Valentino - Having threesomes helped me get over my crippling jealousy
I’ve always lived life by my own rules (Picture: Jamie Valentino)

At my front door, I tried my best to explain why he couldn’t come up: ‘If you really want to try dating, we can sleep together when we next go out.’

I said this knowing full well he’d have to jump on another plane. This time, just for me. John couldn’t have been more agreeable and understanding, even if he was just faking it. 

He’s since told me he worried I didn’t sleep with him because I had lost my attraction and was trying to be polite. I explained the irony was that it was because I liked him too much. 

At the end of the day, a one-night stand is often dismissed – if not outright denied – as a path towards finding love. So I want to buck that assertion.

I’ve always lived life by my own rules, which means I can be slutty one evening and a prude the next. And just because I sleep with someone on the same night as first meeting them, it doesn’t mean we can’t grow from there.

Jamie Valentino - Having threesomes helped me get over my crippling jealousy
We’re currently more than anonymous lovers, less than boyfriends (Picture: Jamie Valentino)

I will always do what I say and say how I feel. That’s why I only needed two encounters to ask John to go somewhat steady, dating with open borders.

So we’re currently more than anonymous lovers, less than boyfriends. We both acknowledge that we haven’t spent enough time with each other to solidify a formal relationship or ask each other to stop seeing other people. But we’re both keen on the idea. 

Hopefully, as he has plans to visit again this month, and I’m flying to LA for a party he’s hosting in August, we’ll decide if what we have is worth the distance. 

And to people who’d turn their noses up at the idea that you can find love through a one-night stand, I’d say they underestimate the power of sexual chemistry and where there’s a will, there’s always a way.

At least if you figure out that person’s social handle. 

*Name has been changed

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