When Should You Have Sex With a New Person You’re Dating?

Photo by my lovely wife mb. Just imagine this is me trying to decide whether to take you home after a date or send you on your way…

Have you ever heard of the “three-date rule,” i.e. the idea that you should wait until the third date to have sex with a new person? I think I first encountered it in some hackneyed sitcom or rom-com, and I remember feeling confused by the very notion. How could you standardize that decision, I wondered, to the point of being able to put it on a calendar? Wasn’t it person-dependent and situation-dependent? Shouldn’t sex progress at the pace of both people’s comfort, whether that’s fast or slow or anywhere in between?

Admittedly, I wasn’t sexually active yet, so I was pondering these questions in a theoretical way, without any real-world experience to inform my thinking. But when I did start having sex, that was indeed how I approached it: no set timeline for when it should or shouldn’t happen, aside from “when we both want it to.” I’ve had sex on first dates when the vibes were right, and I’ve also waited months to have sex with someone, either due to logistical factors like distance, or because it took that long to build the amount of comfort and rapport that one or both of us needed. The timing of first times is as variable as sex itself, and I think most people would benefit from flexibility in this regard, rather than clinging to rigid rules.

That being said, I think there are some interesting arguments on all sides of this debate, so today I thought I’d explore some of the pros and cons of waiting a while to have sex with a new person. Let’s dive in (or tiptoe in slowly, if you prefer)!

 

Pro: More time to develop a sense of comfort & safety

For some of us, sexual arousal and excitement can’t really exist until comfort and safety have been established. Hell, I don’t even feel able to be authentically me until those things are established. Early dates can easily put me into a performative, “customer service”-y frame of mind, because I haven’t yet determined whether this is a person I can safely relax and be myself around. When I’m in that headspace, I have so little awareness of my own desires and bodily sensations that I can’t even effectively determine if I’m attracted to someone or not, let alone whether I want to have sex with them. But once I’ve spent some time waiting for intimacy to develop, my anxiety starts to lift, and I feel more able to discern what I want, and to ask for it without (much) fear of it going awry.

 

Con: Sex is great & you shouldn’t have to deny yourself sexually

A lot of the arguments against having sex “too early” are extremely gender-essentialist, heteronormative, and (dare I say it) heteropessimistic. Dating guides for women often say something like, “Making a man wait for sex is a good way to test whether he actually likes you and is in it for the long haul.” I take issue with the core assertion underlying this advice, which is that men care about sex and women don’t, so women can gain power over men by denying them sex.

You know what you actually get when you deny men sex? Zero sex! (Or at least, zero sex with those men…) That’s okay if you don’t care about sex, or if you’re sufficiently satisfied by your solo sex life that you don’t particularly crave partnered sex at the moment – but if you like sex, and want it, and hope that it’ll be a significant aspect of any relationship(s) you get into, then it makes no sense to withhold that from yourself. What could be less feminist, in fact, than denying yourself pleasure because of how men might perceive it?

 

Pro: More time for attraction to build

Some of us – myself definitely included – develop attractions slowly over time, rather than instantaneously on sight. This is one of the reasons one-night stands don’t work for me (and trust me, I’ve tried): while sex without attraction can sometimes be fun, it’s not hot for me, and it’s not what I want at this point in my life. So I need to know someone decently well before I’ll want to have sex with them. These days I’d always rather wait than risk rushing into sex that ends up making me feel uncomfortable or grossed out.

 

Con: You should assess sexual compatibility ASAP to avoid wasting time

Picture this: You let a fun flirtation simmer for weeks, or even months, until the yearning hits critical mass and you just have to fuck… but then you do, and it becomes immediately clear that they’re a submissive and you hate domming. Or they refuse to give oral sex and it’s the only way you can get off with a partner. Or they’re uncomfortable with you using your favorite vibrator during sex. Or the way their kisses taste is off-putting to you on a pheromonal/gut level. I could keep listing potential sexual mismatches forever, but you get the idea!

Early dating is largely about assessing compatibility, and for most of us, sex is a fairly important thing to be aligned on. So I completely understand why some people prefer to have sex sooner rather than later, so as not to risk the heartbreak and disappointment of becoming emotionally invested in a round peg that’ll never fit your square hole.

 

Pro: More time for STI testing & important pre-sex conversations

Depending on your safer sex boundaries and when each of you was last tested, either or both of you might want to get a panel done before you start having sex. That can take time – in my city, you can often get results back within a few days or less, but that’s assuming you’re able to get an appointment quickly (if needed) and have enough spare time in your schedule to go ASAP, which may not always be the case.

Aside from discussing STI status/testing, you may also want to discuss other matters of relevance before having sex for the first time, such as your kinks, fantasies, limits, and triggers. These conversations are important and I prefer to be able to take my time with them, instead of feeling rushed.

 

Con: Sex makes you feel more attached to each other

Contrary to the popular (and problematic) belief that a man will only develop romantic desire for a woman if she makes him wait for sex, the neurochemicals released during and after sex actually help a lot with bonding and intimacy. (And not just for straight people, either – for everyone!) So if you’re dating someone new and it’s going well, you might be able to take things to the next level emotionally by taking things to the next level physically.

 

Pro: …Sex makes you feel more attached to each other

Yep, it’s both a pro and a con! Sparkly sex neurochemicals can make you view your new paramour through cum-colored glasses. If you want to stay as level-headed as possible while riding the infamous New Relationship Energy wave, you may prefer to postpone sex until the initial romantic reverie has dissipated a bit. Otherwise you could end up smitten with someone who, it turns out, doesn’t treat you well or isn’t a good match.

 

Dear readers, what do you think of all this? Do you have any personal policies about when to have sex with a new person, or do you just play it by ear? Feel free to let me know in the comments!

 

This post contains a paid link. As always, all writing and opinions are my own.