‘Should I Sleep With Someone I’m Not Sure About?’
How sex factors into forming a long term relationship
Modern dating can go in the bin. It permeates conversation with single friends; most of us have no idea what we’re doing in the arena of love. So it didn’t come as a huge surprise when a friend asked me: “I’m not sure about her yet; do you think should I just sleep with someone I’m not sure about?” This question presented itself as a moral quandary fit for any modern dater.
Sex, after all, is something we don’t have good enough conversations about, enough of the time. Which is why, when you’re getting to know a potential lover and discovering their various quirks for the first time, it’s a sticking point. With so little to go on, everyone doing their best to represent their best selves with no flaws, and with modern dating turning us into disposable currency, sex can seem like a huge symbol to some and the equivalent of casual chit-chat to others.
I don’t believe there’s a one-size-fits-all answer, but there are certainly some good questions to ask yourself, if you’re contemplating sleeping with someone you’re hoping will become a longterm lover (but haven’t quite figured out if you’re into, yet)…
How important is sex to you in a relationship?
I have dated people with all levels of sexual desire — from vital to very optional. Is it important that they are generally “good” in bed, or are you looking for a different kind of connection? Sex is a make or break for some, not so for others.
Do you consider sex a key way to get to know someone generally?
This is about how you prefer to learn about someone. Do you need to have sex with someone to decide if they’re a suitable partner? I have always thought of sex as another layer of intimacy or connection with someone I think I already approve of — for me, it is part of getting to know someone, but it’s a much more intimate level of ‘knowing’. This is why the drunken one night stand has never suited me; I view sex as a way to get to know someone better, who I already have some thoughts or feelings about. It’s absolutely about another layer of connectivity for me. But this may not be the case for you, so the question is really about how you want to know someone — at what stage do you prefer to get more intimate? Would you rather get it out the way up front, or save it for down the track?
What do you notice about how they carry themselves?
Many will say you can’t know whether you’re really compatible until you actually do the deed. On the other hand, I’ve generally had an idea or a sense of the person’s “prowess” and our potential compatibility between the sheets, well before any of the clothes come off.
This breaks down into a few things. Part of it is purely physical — how do they carry themselves? Are they comfortable in their own body? How do they move? Do they show signs of easy physical affection? For me, physical touch and affection is super important — this might not be a warning sign to others as it is for me, because for me, it’s a huge deal. But if someone is awkward about holding my hand, chances are that anything more is going to feel strained to me as well. A lot of these details — the small movements, the in between actions — tell me a lot about how comfortable, how free and how open a person is going to physically be with me.
What do you notice about how they communicate?
The other key thing to observe is to do with communication. If anything, this to me is more important than any physical signs. Communicating with our fellow human is never easy, but an unwillingness to try or a real lack of instinct in this department makes sex likely to be a bad time. This isn’t to say that you have to communicate a particular way — communication is made up of many things.
If a person isn’t interested in listening, or a bad listener, if they cant focus on anyone but themselves, if they never remember or take note or ask anything about you, if they don’t appear to be curious or take you seriously… well, all of these things give you a clue. You can’t be good at sex or have a good sexual connection if you aren’t willing or interested to connect in any other sense. Full stop.
Does the person seem ‘good’ in other ways?
I’ve certainly given people the benefit of the doubt; I’ve given in to the hope that, despite being a little underwhelming in other ways, a person might well be more inspiring in bed. I’ve hoped for sex to make up for what is lacking elsewhere. But so far, that has never proved effective. If we don’t connect in life, we don’t connect in bed. Nobody has ‘blown me away’ with their sexual prowess so much that it made up for their being kind of a shitty person. Never.
This might well be to do with my bigger picture values — I value a deep and open connection, and this is largely emotional or intellectual, before it is physical, for me. Don’t get me wrong, a good sexual connection is vital to me, but it isn’t the first thing — I have to connect with the person in another way first. For me, there’s a difference between the ‘good enough sex’ of a physical-only relationship and the amazing sex of a multi-level, multifaceted and connected relationship.

A few final thoughts…
What would ‘sure about someone’ even look like?
If I’m unsure about someone, how can I become more sure? If I don’t know them super well, how can I get to know them on a deeper level? As we’ve discussed, sex is certainly one way to do that. But I want to prod this idea of certainty a little. At the risk of dissolving into solipsism, how can we really ever be sure about anyone? People do surprising things — whether you’ve known them a minute or a lifetime. We can never really know what they are thinking. So what would ‘certainty’ even look like, or feel like?
It takes a great investment of time and energy to ever really get to know someone properly. Sex with a potential partner therefore might well be something you have to consider, before you’re certain about them as a partner (of course, if you’ve got a strict religious or other code, maybe this isn’t a factor). At the same time, instincts count for a lot. With a strong feeling about someone can come what feels like ‘certainty’.
In reality, sex is for many a vital part of a relationship. It often separates a friendship from something more (unless of course you are asexual or simply believe in chastity). A strong and meaningful sexual connection (or conversely, a terrible one), does tend to move the needle on a relationship and on certainty somewhat.
We all need the time to get to know someone, and we all get to know others in different ways. In my mind, the most important thing is that you aren’t using anyone — you aren’t taking advantage, judging them harshly, or being deliberately harmful in any way. Get to know someone in the spirit of genuine interest and excitement; give that person who you’re interested in the time to show you who they are, and the time for them to know you. We don’t all have time for everyone though, so of course you have to be judicious about this. Sleeping with someone may or may not be a shortcut. Do what you feel is right — as long as everyone’s on board.