How to have a holiday fling with a stranger without breaking your heart

They say forbidden fruit tastes the sweetest, and a holiday fling with a stranger can be a fun, carefree experience—after all, when will you meet that hot Spaniard again on your Eurotrip? The idea of diving head-on into an instant connection, free from the pressures of long-term commitment, does seem very enticing. But remember, all good things—no matter how long or short—come to an end. While a casual fling sounds thrilling, it’s important to stay grounded and approach it with awareness and maturity to avoid any heartbreak and disappointment once the trip is over.

So here’s everything to keep in mind about a having holiday fling. 

Know exactly what you want

Intent is everything, so start by understanding what you're looking for. Is it just some short-term fun, or are you hoping for it to develop into something meaningful and lasting? Holiday flings usually lean towards the former, so be honest with yourself. Either way, ensure you're comfortable with the idea—it will help you maintain a healthy mindset and enjoy the moment without overthinking or over-investing in the experience.

Be on the same page with your fling

Ensure you're both on the same page by communicating clearly and keeping things light and casual. If one of you wants something more serious, it's always best to address it honestly to avoid leading them on or creating any misunderstandings. Being open and honest, even in casual situations, is always the right thing to do. 

Things may be casual and fleeting, but decide what you’re going to be comfortable with and set clear physical and emotional boundaries. It’s easy to get swept up in the excitement, but remember to never cross your limit. Try not to open up too much with a stranger who you’ve just met on a holiday or make future plans with them. Maintaining this emotional distance can help prevent heartbreak and disappointment should you get serious but they don’t.

If things start moving too fast, don’t hesitate to assert your boundaries and take control. That said, don’t feel guilty about having fun—it’s completely natural to enjoy a casual holiday fling as long as you stay true to yourself and your boundaries. 

Do not create sandcastles in the air

There’s a good chance of you thinking about the future with your fling while you have fun with them. Keep yourself grounded by remembering this is just a fling, not a long-term commitment. One way to do this is to focus on the present and enjoy the experience. Let go of expectations and avoid overanalysing every interaction and looking for hidden meanings. 

Whatever you do, stay safe

Always prioritise safety and consent. Use protection during sex, discuss health concerns openly, and ensure mutual comfort at every step. Be mindful of emotional red flags like coercion, and maintain clear boundaries to keep the experience positive and healthy.

If you notice feelings developing or sense they're becoming too invested, it's a clear sign to step back. Ending things early helps prevent unnecessary emotional pain and keeps things from getting complicated. It's wiser to walk away while it's still lighthearted than let it turn messy.

If they ended it before you were ready, don’t take it personally—it doesn’t mean you weren’t good enough. A fling is a temporary experience, not a reflection of your worth. Avoid wasting energy waiting for a follow-up; if it happens, great, but if not, move on. Take some time to reflect on what you liked, didn’t like, and learned. This insight can guide you toward the kind of relationship you truly want—or even make you reconsider flings altogether.

Lead image: Amazon Prime Video

Also read: How casual sex affects your mental health

Also read: Things to keep in mind when you're having sex with someone for the first time