Ask Kait: A Shy Person’s Guide to Initiating Sex

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Anonymous asks:

What’s the best way for someone who is shy to initiate foreplay?


Like most things with sex, we’ve been told one specific narrative about how to initiate it. And it’s one that seems easier for those of us with big personalities. Whether or not that’s true is a different story, but it’s hard to be what we can’t see. And if media only shows us limited types of initiation—the frantic coming together, the hyper confident are we doing this?, the mind reading, “I could tell by their body so I jumped in”—then it’s hard to see how someone who’s shy fits in. 

Reflect on your fears and what’s holding you back

Once you have a deeper understanding of your fears and the stories that you tell yourself—about being shy and about what initiating looks like—you can begin to both address any self-judgments and misunderstandings and make an action plan. 

I recommend looking at these on four levels: personal, interpersonal, institutional/communal, and societal. For example, body ideals vary across cultures. The messages you received about your body will vary depending on factors like your race, where you grew up, your body shape, etc. 

Work on healing the judgments that hold you back

Once you’ve identified the stories, work on releasing them. This can be done with the support of an affirming helping professional (e.g. a coach, educator, counselor, therapist, social worker, etc.) as well as through your own work such as journaling, meditations, and affirmations. There’s no single path to healing and you know your body best.

Make an action plan

At the same time as you heal those judgments, begin to make an action plan. A good question to ask yourself is, “How can I be me and also initiate foreplay?” 

Remember: when it comes to sex there’s no normal—only more or less common. You get to choose what initiating looks like for you, not what any sexpert or piece of media (e.g. magazine, website, movie, or romance novel) says. 

Plan for the worst case scenario

My sex coaching and couple’s counseling clients love using “If/Then” planning to map out all the scenarios—from perfection to worst-case!—and how to respond. 

Sitting with all the things that can go wrong is never fun so spread this step across a few sittings if you need. 

Share your plan with your beau(s)

What does your beau need to look out for when you’re initiating sex? How would you like them to respond? Bring them on as a co-conspirator in the process. This way they can respond to your overtures. 

To illustrate, let me share a story from one of my Latinx clients. She loved flirting. For her, it was part of her identity to be sly and slippery versus jumping right in. Since her partner knows this, they can respond by dancing with that flirtation.

Take Action

You’ve got a plan—time to put it into action. Reconsult your If/Then list and go for it! 


What went well? What didn’t? How did that feel to do? Take some time to reflect on your experience, what you’d like to keep the same, and what you want to change for the next time.

Try, try again!

I won’t lie: there’s a good chance it’s going to feel awkward AF the first few times you try. There’s not a great way around this as it’s true for almost every new thing we try, sexual or otherwise.

But you are prepared. So keep going. And don’t be afraid to refine the process along the way.

Still struggling? “Try on” being the sexual initiator you want to be.

What would that person do? How would they act? Pretend to be them and take steps from there.



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