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How to Make the Most of a Vacation Fling, According to the Experts

by Georgina Guthrie Apr 13, 2022

Ahh, vacation. Piña coladas, balmy evenings and long, carefree days by the pool. From the food to the views – everything’s better on holiday, and if you play your cards right, a romantic fling can be pretty good too. OK, vacation flings are usually doomed in the long-term department, but if you think about it, that’s exactly what makes them so exciting.

So what if that cutie you met on the beach turned out to be a cryptopro who only knows how to play Wonderwall? You can ditch them as soon as the sun’s up — and so long as that’s all you both wanted, it’s nothing but a happy memory.

That’s not to say long-term success is impossible — but more often than not (93 percent to be precise, according to research from Tripadvisor), holiday hookups fall apart once the responsibilities of life enter the equation. So enjoy it while it lasts. Be swept away. Be seduced, and ride that sexy wave with the knowledge that your fling is a temporary thing, and that’s part of the charm.

To help you on your way, we spoke to sex and relationship experts Annabelle Knight and Jess Wilde.

Annabelle Knight Bsc Dip is one of the UK’s leading experts specializing in dating, sex, body language, and relationships. She has qualifications in couples counseling, life coaching, and has a diploma in psychosexual therapy. She has helped many civilian and celebrity couples personally and is currently acting body language expert for ITV’s Ready to Mingle.

sex and relationships expert Jess Wilde

Photo: Jess Wilde

Jess Wilde is a writer and director, known for The Sexual Happiness Podcast, Sex and Other Stuff and Bondage Gone Wilde. Her taboo-busting advice has appeared in international publications, on broadcast TV, radio, and on-stage. Now let’s find out exactly how to make your vacation fling sizzle!

These interviews have been edited for length and clarity.

Figure out what you want from your fling

OK, so kids and marriage are probably off the cards (sorry to break it to you), but trust us — that’s a good thing. Not seeing what someone is like IRL means you get to while away those sun-drenched days in a state of permanent honeymoon — without the comedown.

The deciding factor between a fling that’s fabulous and one that’s a flop? Communication.

Yes, just like with dating back in the real world, figuring out what you want (and then telling that to the other person) is central to making it work.

“Is this a fortnight of frolics, or a one-night-stand? Whichever it is, make sure you’re upfront and honest about what it is you’re after, and, make sure your holiday romance extends the same courtesy to you. A broken heart on holiday is not what you want”, says Annabelle Knight.

How to have a one night stand on vacation

The average American worker is entitled to 16 days of paid leave — but the average vacation lasts just over four days. That’s not a lot of time to spark up some romance. Or is it?

“Holiday romances are like normal dating, but quicker! Subtlety is not your friend here — make your intentions known so that the fun can start as soon as possible,” says Annabelle.

Obviously don’t be sexually aggressive — but if you like the look of that cutie by the bar, why not saunter on over for a chat? It’s not like you’ll see them at work on Monday if they do turn you down. Plus, everyone’s stringent romantic standards fall to the wayside when cocktails and balmy evenings are involved — and a smile, a carefree attitude, and a rendition of Wonderwall could get you way further than they normally do back home.

Use a vacation fling to experiment

“Always wanted to try something in the bedroom? Well, here’s the perfect opportunity to see if it really floats your boat or is best off left as a fantasy”, says Annabelle.

Vacation is the perfect time to reinvent yourself. You’re away from home with no responsibilities and surrounded by people you’ll (probably) never see again — it’s the perfect environment for trying out a new you. We’re not talking an Eat, Pray, Love style overhaul (although feel free); we’re talking a new outfit, a fling with that Bardem lookalike, and wild sex — the kind of which is only possible when you know you’ll bid adieu to your hookup once the sun’s up.

Not that we’d be so bold as to make suggestions here, but beach sex is de rigour (don’t do it somewhere you’ll be arrested, and watch out for sand) — as is shaking sheets in the hostel room (make sure you’re alone; you don’t want to be that couple).

How to use sex toys on a vacation one night stand

If you use toys or lube at home to enhance sex, then bring them on vacation, too.

“Lube — like this vegan-friendly option by So Divine — is a great accessory to have handy during intimate playtime”, says Jess Wilde. “Not only does it make everything feel slippery and extra pleasurable, but it can also reduce friction and the likelihood of microtears, leading to safer sex. Just make sure it’s under 100ml if you’re packing it in your hand luggage!” she adds.

Oh, and when it comes to bringing sex toys through security, remember to do your research to make sure you get your babies through the gate without a hitch: no one wants to start their vacay off with Karen at customs waggling your Mega Thruster 3000 around.

How to have safe vacation sex

Sun, sea, and…STIs? Not on our watch!

No-one wants pube crabs as their primary souvenir, so don’t get swept up in the moment so much that you forget everything you learned in sex-ed. “Safe sex is always important, but possibly even more so when you’re hooking up with someone you may never see again”, says Jess.

“Taking responsibility for your own sexual health and the health of the person you’re getting frisky with isn’t just good practice, it can be a real turn on too. Not to mention no one wants to be thinking about how and where to get the morning after pill or a course of antibiotics for an STI when on holiday. If you think sexual contact is on the cards, make sure you have the relevant contraception to hand. Remember: hormonal contraceptives like the pill don’t protect against sexually transmitted infections so it’s always safest to double up with a barrier method (like condoms or a dental dam)”, she adds.

How to safeguard yourself and your emotions

We’re all guilty of throwing caution to the wind when we’re on vacation, but remember not to let your guard down a little too much.

“If you’re off out and about with your fling, make sure you tell someone where you’re going. If the only place you’re going is their hotel bedroom, then take precautions and don’t do anything you’re not happy with”, advises Annabelle.

Red flags include a partner who insists on unprotected sex, someone who wants to introduce toys/sexual practices without consent, and someone who’s too drunk or high to give proper consent. Basically, trust your gut, keep your wits about you — and where sex is concerned, err on the side of caution.

Consider your surroundings

The slogan “What Happens Here, Stays Here” was part of an advertising campaign for Las Vegas that came out in 2003. But you know what wasn’t around in 2003? Smartphones.

The truth is, no matter where you are, anyone with a phone can capture your moment of debauchery and share it with the world (or your friends). And that’s something to keep in mind.

“It can be easy to get caught up in the moment and lose yourself when on holiday and, whilst that in itself can add a lot of excitement to a holiday fling and give you more freedom to experiment, it can lead you to forget your surroundings and act in ways you wouldn’t back at home”, says Jess.

“It may feel risk-free — after all you’ll probably never see these people again — but social media is everywhere nowadays and you may not want your work colleagues to see you in the background of a tagged photo with your skirt around your head. Don’t do anything you might regret later!” She adds.

Know the local law

“Speaking of acting without inhibitions, you don’t want to accidentally land yourself in real hot water. Different countries have different laws (and punishments) when it comes to sex, so if you’re planning on taking a risk (like enjoying a little al fresco sexytime, for example), make sure you know exactly what risk you’re taking,” says Jess.

“Some countries have very strict laws when it comes to indecent exposure, public fornication and even sex toys. A holiday fling is supposed to be fun, not land you with a hefty fine or worse, behind bars.”

It’s also important to know your destination’s stance on LGBTQ+ rights. There are still countries that criminalize LGBTQ+ people, so if you are in this environment, take extra care to keep yourself safe.

Learn the basics of the local language

Flirting requires a way with words — something you’ll probably struggle to master with four minutes of Spanish Duolingo under your belt. While wooing your holiday cutie in their own language is probably a bit ambitious, it’s a good idea to make sure you’re able to communicate the very basics.

“Getting with someone who doesn’t share the same first language as you can be hot (who doesn’t love an accent), but it can also create some issues with understanding each other”, says Jess.

“Just make sure you have figured out some way of communicating clearly with each other so you can properly establish boundaries and get across what you like (or don’t like) when it comes to playtime,” she adds.

Don’t miss out on your trip because of a vacation fling

So you’re on a vacation high and you’ve just met a Javier Bardem lookalike. You’ve listened to a sunset rendition of Wonderwall. You’ve gotten lost in the market, danced the night away in a smoky bar, shared passions and dreams (way more interesting in a sexy accent)…is this…could it be…?

Hold it right there.

You’re on a vacation high and the rose-tinted specs are on. And that’s ok! But sorry to break it to you — it ain’t love. Taken out of the romantic vacation bubble, this thing would never last back in the real world. Probably. But you know what will? Friends. And the memories of that scuba trip you were supposed to go on.

Having a one night stand on vacation is fun, but they should enhance your trip — not dominate it. “Remember you’re still on holiday, try not to leave your friends stranded and try to do at least some of the things you’d planned before you left — you don’t want to fall out with friends over a fling” adds Annabelle.

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