Never Have I Ever: Had a Hot Valentine's Day Hookup

Here’s What It’s Really Like to Have a Hot V-Day Hookup in a Hotel Room With Your F-Buddy

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

As Valentine’s Day approaches, the pressure rises. Frankly, it’s a shame, as a celebration of love should be fun, not daunting.

However, as anyone in a relationship, especially a new relationship, knows, the holiday can come with a lot of pressure. Should you send flowers and risk freaking someone out, or ignore it and risk pissing someone off? It can be hard to win. And, if you’re single, even though it is just a silly holiday, it’s easy for the rush of pink and red and hearts and cupid to leave you feeling lonely and down in the dumps.

For Mike, a 34-year-old creative in Los Angeles, the perfect solution to Valentine’s Day came in the form of a long-term fuck buddy. Keep reading to learn why a friends-with-benefits situation can be perfect for romance, the danger of fucking on rose petals on white sheets, and how to find your own fuck buddy situation that allows for rose-stained romance without any of the pressure.

AskMen: So you mentioned that a few years ago, you had an incredibly intimate, yet casual, Valentine’s Day, while single. How did you manage that?

Mike: Well, it starts with a unicorn of a fuck buddy. One of my best friends from college (I’m 34 now, so technically, we’ve been sleeping with one another for over a decade, perhaps making this my longest relationship ever), Annie, is also a fuck buddy.

The unicorn, not like in a threesome (although I’d be down) but that one-in-a-million situation that just works out. We were neighbors in college; she’s two years older than me, which seemed like a lot when I was 19, and she was 21, but now it means nothing.

Anyways. In most of my experience, friends-with-benefits situations go up in flames because someone catches feelings. You start out with friends and fucking and end up blocked on IG.

But Annie and I would hook up whenever we were both single in college, and we’ve continued the tradition. I live in LA, and she lives in New York, and both our work brings us to the other at times. If we’re both available, we stay with one another and fuck (and also have fun as good friends).

And before Covid, in 2019, you ended up having a romantic Valentine’s Day, to say the least.

Yes. This is February 2019, when no one knew what was ahead. Annie was in town for work for a shoot; she works in TV and asked if she could stay with me. We’d both gotten out of serious relationships recently, and some hot yet trusted love sounded like just the ticket, you know?

At first, leading up to her visit, we made some jokes about Valentine’s Day. I said I’d get her roses. Then I landed a pretty well-paying gig. I work in media, too; we were both Communications students when we met. I had some money to burn and, to be honest with you, was feeling down in the dumps.

I don’t anymore, but at the time, I thought my breakup was the end of the world. Annie was more settled and happy than I was, but what girl doesn’t want to be treated on Valentine’s Day? I’m rambling. I suggested that we get a hotel room, order room service, and champagne, and fuck each other’s brains out. And we did.

So what was it like? Having such a romantic, dare I say even cliche, Valentine’s Day with someone that you’re not actually dating?

Honestly, the girl I’m dating now better not read this and figure out that it’s me (kidding, she’s cool), but it was probably the best Valentine’s Day of my life (except for this year, sweetie, if you’re reading).

I bought a bunch of roses and covered the bed with them. As I said, we decided to go all out. That was probably the biggest mistake, actually, because, as it turns out, red roses really stain white bedsheets. TMI, but the bed kind of looked like a horror show because Annie was on her period, not that we let it stop us, but from the period blood to the rose stains; I’m surprised the hotel didn’t send the cops after me.

But we talked about our careers, about love, and we had sex a total of five times (the night of and the morning after). Annie brought this couples vibrator that we used together. We ended up filming some of it with my phone. I guess when you get two people in the media together they want to make content, haha. I used to watch that clip all the time, especially in the dark days of Covid. It was a kinky night, the most on-the-nose Valentine’s Day I’ve ever had, but damn, it was hot. Sweet, too.

So, no shade to the girl that you’re currently seeing, but have you and Annie ever considered actually dating after all this time? You sound like you go well together.

We do go well together but as fuck buddies. Honestly, it’s never really come up. I’m kinky, but I feel boring these days. I’m a straight dude who is monogamous and actually wants to have kids and get married eventually.

Annie is on another level. I love and respect her for it, but in college she said she couldn’t settle down with anyone because she was too young, and now she has a whole polyamorous queer life in New York City that I just can’t keep up with. She doesn’t think about things like getting married or having kids.

And long-distance is not something that would work for me, because I am monogamous. I am romantically satisfied with my current situation. I’m telling you about this night for your column because you asked, and because Annie is dope, but no, we aren’t meant to be romantic partners. Like I said, it’s a unicorn situation.

Have you ever thought about making her a threesome unicorn with your current partner?

Yes, I’ve thought about it, but while Annie is bi, the woman I’m seeing is straight, and I just don’t see it happening. That’s OK.

Makes sense. Back to Valentine’s Day 2019. Why do you think you ended up having the best time with someone who you’re not really romantically involved with?

It took all the pressure off. Everything is easy with Annie. We went big and cheesy for the hell of it. There were no worries about, like, what gift to give her, or what it means like there usually is the first time the holiday comes around when you’re just starting to date someone. That’s pressure. With Annie, it was just an adventure.

What advice do you have for others reading this, hoping to find a similar friends-with-benefits situation?

Listen to women. Or whoever you’re dating. If someone says they want a relationship, don’t expect them to change their mind and be down with a casual setup. Annie and I have always been honest about who we are and what we want, and never tried to change that.

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Source: AskMen