How to Prepare For a Casual Sex Date

I’ve written to you before, dear readers, about my fascination with casual sex. It was one of my sexual goals for 2015 to have casual sex at least one time, and I defined it thusly: “sex with someone I am not, and do not intend to be, in a romantic relationship with.” And by that metric, I have indeed achieved this goal as of late. Hooray!

As an anxious person, I like to be hyper-prepared for every eventuality. And this is why, before a potentially nerve-wracking situation like a hook-up, I have a pre-game ritual that gets me happy and hyped while keeping me safe and sound. Whether you’re finally gettin’ physical with a long-time crush or just looking to meet a fuck buddy online for a quick bang, I hope these tips will be helpful to you!

 

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Physically…

• Do whatever “body maintenance” is going to make you feel sexiest and most confident. Shave your legs, trim your pubes, groom your beard… Condition your curls, paint your nails, exfoliate your lips… Rinse your vag, scrub your balls, wax your butt… Whatever’s going to amp up your self-esteem for the evening, do that. Try not to let conventional beauty standards muddle your own personal standards too much, because if your date doesn’t enjoy the typical state of you, you probably shouldn’t be fucking that person anyway, right?

• Pick out an outfit that makes you feel hella desirable and cute. Bonus points if it’s relatively easy to remove in a hurry (you never know when things will suddenly get sexy) and if your undergarments are on-point.

• Get checked for STIs if it’s been more than a reasonable amount of time since you’ve done that (i.e. if you’ve engaged in any potentially risky sexual activity since your last test). Know the score before you get in the game. That way, you can confidently tell your partner what’s up and neither of you will have to worry. (Hopefully they’ll be as considerate as you in this regard!)

• Stock your bag and/or pockets with any sex supplies you’ll need. Fragile stuff like condoms and dental dams should ideally go in some kind of hard case to keep it safe from heat and warping (don’t cram your condoms into your back pocket and then sit on them all night!). If you bring a vibrator – which, if you like vibration, you should; don’t let anyone shame you! – do your best to pick one with a travel lock function, or at least place it in your bag in such a way that it won’t turn on before you want it to. If you want to be extra prepared, bring along some lube samples as well.

 

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Mentally…

• If you have any hangups whatsoever around the sex you’ll be having or the person you’ll be having it with, I prescribe a good long journaling session. Ask yourself: how do I feel about this? What do I hope will happen? What do I hope to get out of this? What is it that I like about this person? Where do I see this going? Some people are blessed with the ability to have sex without overanalyzing it, but if, like me, you just didn’t get that gene, journaling may help you get your head on straight.

• Consider your dealbreakers and know when you’d walk out. This is a scary thought, but it’s worth thinking about in advance. If someone exhibits a red flag, like refusing to go down on you or making a weird comment about your body, it’ll be that much easier to get up and leave if you’ve already identified your red flags in your mind.

• Figure out where you’re going, how you’ll get home, how much transportation will cost, etc. Don’t get stranded! And since casual sex goes hand-in-hand with intoxicants for some people, make sure you know this information well enough that you could recall it even if you were kinda tipsy (or more than “kinda”). Don’t be that shitfaced sadsack on the subway who can’t figure out where the hell they’re going.

• While you’re getting dressed, doing your face/hair, etc., put on a playlist that puts you into the optimum sexy mood for your fuck-date. I am all about Alina Baraz and Reverie Sound Revue; there are also tons of sultry mixes on 8Tracks that’ll help you get your vibe right.

 

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Verbally…

• I know it’s hard, especially if you’re shy, but try to establish some expectations with your sex-partner-to-be. It’s tough to be brave and say exactly what you want and what you don’t want, but it’s worth doing to avoid the hassles that accompany miscommunications. What if you like your casual sex with a side of cuddling and talking about feelings, but your potential fuck-buddy just wants to get ‘er done and leave? What if you absolutely hate sleeping next to someone but your dalliance expects to stay all night? You don’t necessarily have to spell these things out so explicitly, but try to read the person’s tone in your communiqué, at least, to get some sense of whether you’re on the same page.

• Think about what you want and practice asking for it. This can be especially hard with someone you’ve never slept with before and/or don’t particularly intend on sleeping with again, but it’s worth doing if you want your experience to be a good one. People generally enjoy knowing what’s expected of them and being asked to do sexy things in a respectful, polite way, so if you can nail that skill, you’ll ensure a more fun time for both of you.

• Tell a friend or two about your plans. Fill them in on where you’re going, when you expect to be back, whether or not you’ll be reachable, who you’re going to see, and where potential sexytimes might be taking place. If you’re worried about your safety, maybe set up a codeword system with a friend: she’ll call you at a specific time and you’ll have a fake conversation, during which you’ll casually use a particular word if everything’s fine, and a different word if things are going downhill and you need her to send help.

 

What’s your pre-sex-date ritual? Do you define “casual sex” differently than I do?

 

Note: this post was sponsored, but as always, all writing and opinions are my own!

  • Great advice. I wish I’d had something like this when I was in my casual sex phase of our open relationship. I actually made some very stupid, risky decisions (like getting in his car and going somewhere remote)