How To Figure Out How You Really Feel About Casual Sex

Ashley Batz for Bustle

We’re always hearing that we could be having better sex, a better orgasm, or a better relationship. But how often do we hear the nitty-gritty of how we can actually better understand our deepest desires and most embarrassing questions? Bustle has enlisted Vanessa Marin, a sex therapist, to help us out with the details. No gender, sexual orientation, or question is off limits, and all questions will remain anonymous. Please send your sex and relationship inquiries to Now, on to today’s topic: how to make your own rules about casual sex.

Q: “I'm single for the first time in four years and I'm feeling weird about it! Overall, I'm feeling really good about being an individual and being on my own. But I am struggling with how to approach dating as a 20 something! I have all these expectations that it should be like Sex & the City — romantically casual, but also fun and exciting — and I should be confident with myself and happy dating around.

But I had a thought the other day: ‘How much do I want to sleep around?’ In the last couple of years, I've stopped thinking of frequent and casual sex as a bad thing. But it was never a thing that I did in the past, so now I don’t know how to approach it — or how I feel about the idea of increasing my 'number.' I just had an OB/GYN appointment where I had to share my ‘number’ with my doctor, and I kinda panicked because it’s higher than it used to be.

Is it okay to sleep around and have a little fun as long as everything is safe and consensual? How do I untangle my desires from these negative feelings? I feel like I'm supposed to hold out for the third date —why?”

A: Thanks for the question! The “when should I sleep with someone new?” question is such a classic struggle for so many women (and men too, for that matter). It’s common to have these kinds of questions, especially when you’re single for the first time in a while. Here are seven guidelines for making your own rules about your sex life.

You’ve Been Taught To Feel Guilty

First of all, you are definitely not alone in feeling guilty about sex; almost every person alive will feel guilty about their sexual decisions at one point or another. Almost everyone’s had that moment of panic thinking about their number, or worried that they slept with someone “too soon.”

We all feel these feelings because we’re taught to feel guilty about sex from a very young age. Our culture has a messed up way of dealing with sex, to put it simply. Women in particular are made to feel guilty about having sex — we’re not supposed to be “sluts,” but we’re also not supposed to be “prudes.” We’re supposed to put out, but not too soon, and not with too many people. It can feel maddening at times.

You Have To Understand Your Own Values...

It’s really important to recognize that those guilty feelings are not necessarily your own — you’ve been taught to feel ashamed about your sex life, but that doesn’t mean those are your actual values. You’re an adult, and you get to decide what you want from your sex life.

One of the best things you can do is start identifying your personal, authentic values when it comes to sex. You mentioned in your email that you don’t see a problem with casual sex from a moral perspective, so it seems like the guilt you’re feeling is probably from external sources. Take the time to think about the beliefs you have about sex, and whether or not you actually want to live your life by those beliefs.

Ask yourself the following questions:

  • “What was I taught about sex?”
  • “Do I want to live by those guidelines? Or do I need to change or alter them?”
  • “What do I think about casual sex? What role do I want it to play in my life?”
  • “How do I know when I’m ready to sleep with someone new?”
  • “How do I know when I’ve made a healthy decision?”

...And Make Your Own Rules

From those beliefs, you can create your own guidelines for your sex life. You get to decide whether you enjoy having casual sex and getting a sense of your chemistry right away, or if you’d like to wait to get to know someone better before being intimate with them.

I know everyone always talks about the three-date “rule,” and gets hung up on their “numbers,” but those are just arbitrary things. There’s no good reason why you need to wait three dates to have sex with someone new. There’s no perfect “number” that every woman should strive for. You get to make your own rules now — and you get to make sure those rules actually make sense to you. Maybe you want to wait two dates, or five, or a month, or until you’ve both been tested for STIs, or until you’re in an exclusive relationship. Or you can decide you don’t want any rules at all!

It’s OK To Sleep Around

I hope I’ve made it clear that your values are the most important ones at play here. But I also want to tell you that it’s perfectly OK to sleep around! As long as things happen between two enthusiastically consenting adults, it’s all good!

Learn As You Go

I know I’ve been talking a lot about planning beforehand, but I also want to say that you can’t always anticipate how you’re going to feel after having sex. You can come up with your own guidelines, but you’re also going to do a lot of learning as you go. Each experience is going to teach you something new about yourself. You’re also going to go through different stages in your life, where you feel more and less open; you can always make adjustments to your guidelines depending on how you feel.

Be Gentle With Yourself

Because our reactions aren’t always predictable, you’re going to inevitably have experiences where you stick to your rules but still don’t feel great about your sexual decisions. Try to resist the urge to beat yourself up in those situations, and recognize that it’s a learning experience.

For example, maybe you have a couple of one-night stands in a row, and realize that it doesn’t feel good to you to do that. Or maybe you go for six months without having sex at all, and realize that you feel isolated and lonely. Those are both important lessons to learn, and they can help you make better decisions going forward.

Remember That Your Own Values Are The Ones That Matter


You’re never going to be able to fully get rid of those voices in the back of your head that make you feel some amount of guilt and shame around sex. So it’s extremely important for you to keep reminding yourself about your own values. When you notice yourself starting to think, “Wow, my number is getting pretty high,” take a moment to remind yourself, “That’s just societal BS trying to make me feel guilty. I feel good about the decisions I’ve made with my sex life, and I know how to make healthy decisions for myself going forward.”