Should You Tell Her You’re Inexperienced?

So for the first time in my life, I’m starting to have some luck dating. I’m sticking to my workout and feel like I’m getting my life and career together. Once I had a little luck, I’ve felt better about asking women out. The problem is though that  because this is all new, I’ve only had sex few times when I was younger, and I feel like I should give them a heads up that I might be a little rusty but I don’t know if there’s a way to do this without making me look bad.

First, congratulations on your hard work paying off!

As for your question, I can give you some guidelines about how to approach this subject if you decide to, but you might want to consider other alternatives. 

There are things you absolutely should disclose before you sleep with someone for the first time—STD status, for example, or if you’re in an open relationship—but I don’t think that this is one thing that you have to disclose.

Let’s break down the thought process behind this question.

In this particular instance, the only reason I can think of that you might feel like you should disclose is because you’re nervous.

Why are you nervous? Because you’re worried that you won’t be “good,” right?

You might feel like there’s some sort of safety in a disclaimer. It’s as if you’re offering them an explanation, like “Hey if this sucks, here’s why.” Or on some level you might be looking to adjust her expectations so she’s not disappointed. Of course, it doesn’t work like that.

Two things to consider:

1) Separate the notion that experience=good sex. Sure, experience is one factor, but so are other things that you may have on your side like attraction, intimacy, and chemistry.

2) By telling her “you’re rusty” or “it’s been a while” all you’re communicating is that you’re concerned that you won’t be able to satisfy her. This is just a statement. You’re resigned to the fact that it will probably be “bad.” Instead of making a statement of “fact,” why not be proactive and open up a conversation that may clue you in to what will satisfy her? Here, you’re doing something about it. It doesn’t matter if it’s been a while if you know what works for the girl you’re currently with.

When you get a good sense that you guys might be heading in that direction soon, capitalize on the topic of sex if and when it comes up: what she likes and doesn’t like; what you like and don’t like; fantasies; what works for her; what works for you; what she’s comfortable with; where her boundaries are; etc.

And continue this conversation during sex. Model for her the kind of direction and guidance you’d like to receive in the moment. Let her know when she’s on the right track. And check in with her in the same way if she doesn’t reciprocate.

But also realize that it doesn’t matter how much intel you gather beforehand, a lot of times it takes more than once to “figure out” what works for new people. So, if you don’t have mind blowing sex the first time, don’t be too hard on yourself. That’s normal for everyone–experienced or not. Tune in to her physical and verbal cues and after a while you’ll find yourself becoming more confident in this arena in the same way you learned to be more confident dating.

As always and above all, know thyself.

At the end of the day, it’s all about confidence, (as it is in many other situations). So, if what’s going to make you feel comfortable, confident, and relaxed is getting it out there on the table, maybe you should tell her. But there are ways to communicate this without it sounding like a disclaimer or an apology.

There’s no one thing that’s going to work for everyone. So really ask yourself what’s going to make you more comfortable and confident?

Does the “fake it till you make it” philosophy put even more pressure on you to perform?

Will you feel more comfortable breaking your streak with a woman you can talk to and have been dating for a while? Or do you feel like there will be “less to lose” with a one night stand?

Take a while to think about these questions and let your gut guide you.

Good luck out there!