At the end of the day, casual sex is what you make of it

If you’re not careful, you might make some horrible mistakes that end in heartbreak, STIs or unexpected pregnancies. But if you’re smart about it (and a little bit lucky), you can take advantage of the fact that strict monogamous relationships are on the decline – and have a grand old time.

Different Types of Casual Sex

It isn’t necessarily just about having a one-night stand with a stranger. It could also be a long-standing friends-with-benefits setup, sleeping with someone who lives far away every time you’re in the same place or anything that’s outside of a defined relationship with clear-cut boundaries, milf hookup sex rules and obligations.

Casual Sex With a Friend

Having casual sex with a friend is a concept that long predates app-based hookups. The hazy boundaries around friendships mean two people can conceal an attraction-based interest under the guise of being just friends until one or both parties lets the mask slip.

It can be a lot of fun to explore the sexual side of a friendship that had thus far been platonic – and a potential gateway to a full-fledged relationship, if you both decide you want more at some point. Since you already know and care for each other, that can make the sex more meaningful and the interactions less awkward.

On the other hand, if you’re not both ready for the shift in your interactions, hooking up with a friend could just make everything way more awkward. After the heady rush of finally consummating your mutual attraction wears off a bit, it can be a quick path to a friendship ending, particularly if you’re not able to navigate what you both want from each other.

Casual Sex With a Stranger

Having casual sex with a stranger instead of a pre-existing friend comes with a number of potential benefits. First, if things go south, you won’t have lost a long-standing friendship. In fact, you might even gain one if you’re able to stay on good terms after the hookups fade out.

However, the drawback with strangers is you never know exactly what you’re getting. Since you don’t know the person well (or at all), it can be easy for miscommunications or misunderstandings to crop up, and what seemed like a person you could have an enjoyable fling with might have been a carefully constructed facade all along.

To that end, you have to do a fair amount of due diligence before sleeping with a stranger – looking them up online, talking to mutual acquaintances, slowing things down until you feel confident that sleeping together won’t be a mistake – or you have to accept the reality that it might blow up in your face at any moment. Your call!

Casual Sex With an Ex

If choosing between casual sex with a friend or a stranger seems like a “chocolate or vanilla” proposition where either could end well or badly with about equal likeliness, casual sex with an ex does not quite live up to that standard. It’s a situation where in the overwhelming majority of cases, it won’t end well.

The excitement of someone you thought you’d never have sex with again consenting to one more (or several more) hookups can certainly be overwhelming. Whether you were the dumpee or the dumper, engaging post-breakup sex can also seem incredibly tantalizing – it’s a bad idea, but you’re both doing it anyway, choosing your sex drives over your emotional wellbeing.

But if you do go through with this, it’s hard to deny that it’s a recipe for things ending on an even worse note than they had before … and for your friends to get an opportunity to deliver you a big, fat “I told you so.”