Dating & Sex, Life

How To Start & Keep A Cheeky Casual Fling

When you’re single, a load of things get easier (no agonising, low-key, ‘what do you want for dinner’ arguments). But navigating the problem of how to get your end away is one that seems to remain as frustrating and difficult as ever. We can see throughout the annals of history, all of us bumbling about, trying to find pleasure, making egregious errors and awkward messes as we go. We can get a man on the moon, but we can’t get a man onto me, as it were. So the casual fling is often tough terrain.

Humans are very weird, awkward and sometimes puritanical about sex and, as Australians, we have inherited that British prudishness that can really stop us all having a good time between two or more consenting adults (or on our own, of course.) I am by no means the oracle on getting laid (not by a long shot, frankly) but here’s some pointers to take with you on your merry journey to fun bedroom times.


Mind games are for hypnotists. Although we all like to think we have a ‘strategy’ when it comes to dating and hookups, it ends up being more effort than its worth and, often, more detrimental to your cause. We generally don’t like to be “confrontational” and that can include saying things that might be considered at all firm, defiant or questioning. Heaven forfend that we might simply vocalise what both parties are already thinking! It’s such a blight on the soul to worry day and night, deconstructing and compartmentalising every word someone has said, making one’s own assumptions, drawing one’s own conclusions and long, oppressive bows.

Although it feels difficult, in the long run it’s much easier to simply lay out your intentions and desires (“I’d like to meet up with you sometime, how’s next week?”, “I think you’re very cute and I’d be keen to hook up sometime, how about you?” Or something more charming), rather than play Messenger-tennis and agonise over how many emojis mean they like you.

That Goes For The Sexy Times, Too

It sucks when you get hyped for a boning sesh with someone and it all falls flat. Being on the same sexual wavelength with your partner/s is key, and part of that comes down to being honest and vocal about what you want. This can be especially tricky if you feel like your particular kinks or desires are unusual, but thanks to sites like FetLife and the post-Fifty Shades of Grey discussions around BDSM, kink and consent, these types of conversations are getting more normalised and mainstream (of course, I am talking explicitly about legal interactions between consenting adults here. I hope that’s clear.)

Telling your partner what you do and don’t like, what makes you uncomfortable and what really gets you off, and making sure you know what they love and hate too in a casual fling, is paramount. This can be trickier with a one-night stand, but it should become easier the more you get to know someone, and having those conversations mean better, more fun sex in the long-term.

If You Catch Feelings, Make It Known

Falling for someone can be the make-or-break moment of a casual fling. If you’ve laid out (hehe) a no-strings arrangement with someone, it may very well have to come to an end if one person doesn’t reciprocate the other’s romantic feelings. It’s tricky terrain, but as you might imagine, the best advice here is to open the wound. Not a euphemism; tell your shag-friend how you’re feeling. Billy Joel, as usual, has the best advice here.

There’s really two ways it can go. Either they reciprocate and you can bounce into the next stage of your relationship, or they don’t feel the same, and wound is open to air, to heal over. So much of our anxieties and arguments come from worry, wondering and unanswered questions; we roll them over in our brains, pitch them to the group chat and ask the internet, but transparency is the best overall option.

Life’s too short for bad lays. Go, you good things.

Image Source: Paramount Pictures

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Writing and podcasting, usually while listening to Phil Collins.

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