How to Express Interest without Being “Creepy”

Have you ever wanted to tell someone you’re attracted to them, but held back because you were afraid they’d think you were creepy? If so, I wrote this post specifically for you. Although this could be people of any gender expression, I’ve noticed it often with cisgender, heterosexual men. Therefore, I will address this article to men who are interested in women, and use correspondingly-gendered pronouns.

We’ve all heard women complain about men who are creepy. It’s been my experience that most men don’t want to make women feel uncomfortable. Some are even so afraid of doing so that they won’t express any interest at all.

In this post, I’ll explore the two main reasons that an expression of interest can feel uncomfortable or threatening—incongruence and pressure—and I’ll show you how you can communicate your desires in ways that invite openness, trust, and genuine choice.

Incongruence

If you’ve ever been criticized for expressing a desire, for experiencing pleasure, for enjoying yourself, or even having fun, you may have made it mean that the problem was your desire. You may have learned that pleasure in itself is bad. If you’ve ever been told that you shouldn’t do something, or if you have seen in movies or TV shows someone else doing that activity and being criticized, ridiculed, or shamed, or if your religion tells you that certain desires, or all desires, or even pleasure in general is bad, it’s easy to assume there’s something wrong with desire and that it should be hidden.

When you’re ashamed of your desires, you may try to express them while simultaneously concealing them. You might hint at what you want rather than saying it directly, or pretend that you’re interested in something other than what you actually want.

This incongruence can create discomfort for the other person. She may sense that you want something from her without knowing exactly what it is. And when someone senses an unspoken agenda, it’s natural for them to become cautious.

Let me tell you something: there is nothing wrong with your desires. It’s okay to want what you want. The problem isn’t your desire, or even your nervousness about expressing it. The problem is the disconnect between what you want and what you’re willing to communicate openly. The solution to this is to express your desire in a way that’s open and direct. In other words, let your interests be seen and known.

The Risk of Rejection—and What You Make It Mean

I acknowledge that it’s a risk to do that. What if she’s not interested? What if she says “no”? Or worse yet, what if she laughs at you or ridicules you for asking? The truth is you don’t know how she will respond, and this is what makes it a risk.

To express desire cleanly, you have to take a risk. You have to put yourself out there. You have to be willing to face the possibility that she might not be interested, or that she will say “no.” I’m not minimizing this. I understand that it’s a big deal.

There will be women out there who are not interested in you. There will be some who say “no” no matter what you ask them. But that doesn’t mean there’s anything wrong with you or your desires. It just means you’re not a match with this individual. Her no simply means that the connection you’re hoping for isn’t something she wants right now. Knowing that frees you to move on and connect with someone who might share your interest.

The goal of putting yourself out there is not to get a specific person to say “yes” in response to a request. Ultimately, the goal is to find and connect with people who accept you for who you are, and accept, even appreciate the desires you have.

If someone tells you she’s not interested, rather than seeing it as a rejection of who you are, consider seeing it as a gift. She’s giving you information about what she wants, or doesn’t want. You don’t have to make that mean anything about your worth, your attractiveness, or the legitimacy of your desires.

There’s a difference between what happened and the meaning you assign to what happened. For example, if you ask someone out and she replies, “No thanks,” what happened is simply that she declined your invitation. But what do you make that mean? These are some possible interpretations. As you read over them, consider whether any of them are familiar to you. In other words, have you created these narratives before in your life?

1. I am being rejected.
2. She thinks I am disgusting.
3. I never should have asked.
4. There’s something wrong with what I want.
5. There’s something wrong with me.

If you create any of the meanings above, it’s easy to start to believe that the same thing will happen in the future, and that no one will ever respond positively to your interest. So you might start to express interest in a way that’s hesitant and indirect, or even make it into a joke so it’s less of a risk. If she says no, you can always claim you weren’t serious. This can lead to the incongruence I mentioned above.

The main reason you feel rejected is not from what happens, it’s from the meaning you create around it. It’s what you make it mean. The more you can be aware of the meaning you’re making and recognize how it’s reinforcing the beliefs you formed earlier in your life, the more you will be able to take the risk.

Pressure

The second reason an expression of interest may cause discomfort is when the request comes with pressure, either intentional or unintentional, for the other person to respond the way you want.

In this culture, men are subjected to a lot of social conditioning (more about that in this post) about what it takes to “be a man,” and a lot of it relates to “success” with women. It’s commonly said that you “become a man” when you have sex for the first time. When a man expresses an interest, not only is there the question of whether he gets what he’s asking for, but his very identity as a man hangs in the balance. This can put a lot of pressure on him. As a result, it’s understandable that he may have a big investment in the outcome, and may attempt to influence the response.  He may attempt to override a no or get her to change her mind.

Women are subjected to social conditioning also. Many women are socialized as “people pleasers” (more about that in this post). People pleasers have been conditioned to do what they can, sometimes even compromising their own preferences or boundaries, to “not hurt his feelings.” 

Even if he doesn’t take explicit action to attempt to influence the response, an intense emotional response can cause him to be reactive. He may get angry, collapse, or withdraw. Any of these can be perceived as a threat and therefore put pressure on the woman to give him what he’s asking for. Just having a big emotional response can trigger a woman’s people pleasing conditioning and put pressure on her to “make him feel better.”

In this situation, cultural conditioning is also working against you. Men have been socialized for generations to try to get what they want from women, to not take no for an answer, and to have a sense of entitlement. So even if you personally are not like that and are sensitive and respectful, it’s very likely she has had experiences of other men who were not, so she may, understandably based on those past experiences, be afraid of how you will respond.

Accept and Invite the No

You can help relieve this tension by making it safe for her to say no to your request. You can do this by indicating, possibly even before you ask the question, that you are willing to hear “no,” with respect and gratitude. It can be helpful to even encourage her to do so. Here are some examples of how that might look. These examples illustrate ways of both expressing a desire while at the same time being attuned to the response.

• “Want to come back to my place? A no is as welcome as a yes.”
• “I’m feeling a strong desire to kiss you, and I want to check in with you before I act on it.”
• “You said you’d go out with me, but you sounded hesitant and uncertain. I want you to know that it’s completely okay to change your mind. I only want to go out if you genuinely want to.”
• “I am lit up with desire for you right now. How does it feel to hear that?”

You may think it’s counterproductive to encourage a “no.” You may ask, “why would I want to encourage the opposite of what I actually want?” It comes back to what I said earlier. The intention of dating or connecting with someone is not just to get to yes through any means. Do you really want someone to say yes to you just because she’s afraid of how you will respond to a no? Do you want someone to hang out with you out of fear? It may work in the short term, but is not sustainable. The only way to create a fulfilling reciprocal relationship is for her to have the option to say no. You have to be willing to take that risk. She has to have full choice and agency in her decision to be with you.

Years ago, I was on a date with someone. We met at her place. At the start of the evening, she said she didn’t want to have sex (intercourse) that evening. I agreed to that boundary. Even though sex was off the table, we were still physical in other ways. We still shared a lot of pleasure and enjoyment with each other. Later that evening, she let me know that she had changed her mind, and that she now wanted to have sex with me. Even though I wanted that and would have really enjoyed it, I declined that invitation. I chose to stick with the original boundary I had agreed to. I said to her, “If we have another date, I’d love to! I’ll be totally down for that! But I’m not comfortable changing our agreements in the heat of the moment.”

Later, I did ask for another date with her, however she declined. She said she was glad we had not gone through with intercourse that night, and appreciated me for keeping that boundary.

In order to do that, I had to overcome a lot of social conditioning. I grew up believing that sex was scarce, and that I had to take it any time I could get it. Such social conditioning reinforces a sense of desperation. In contrast, this experience reinforced in me that my integrity and my agreements are more important to me than getting laid every chance I can.

I believe both of the things that are likely to generate discomfort in the person you’re asking, incongruence and pressure, are attempts to lessen the risk in expressing interest. Incongruence lessens the risk by concealing it in some way. Pressure lessens the risk by attempting, either consciously or unconsciously, to influence the outcome.

It’s vulnerable to take risks like this. You may be tempted to lessen the risk so it feels less vulnerable. However, trying to avoid vulnerability can actually interfere with the very connection you’re hoping to create. 

So, take the risk. Express your interest, then demonstrate that she can say no without facing adverse consequences. Show that you can hear no with grace and presence. You have to be willing to take the risk to express your desires (your part), and then you need to be attentive to her experience also (her part). If either of these is lacking, it’s not true intimacy.

When you make it genuinely safe for someone to say no, you’re also making room for a more meaningful yes. If she says yes because she’s afraid of disappointing you, you haven’t really received what you wanted. What you wanted was someone who freely chose to be with you. The freedom to say no is what gives meaning to yes.

One More Factor: Context

Although incongruence and pressure are two major reasons an expression of interest might make a woman uncomfortable, there’s another important factor to consider: the context in which you express that interest. Even when your intentions are respectful and you’re willing to hear no, the circumstances may affect how comfortable or free she feels to respond.

For example, suppose you ask out someone who’s taking your order at a restaurant. She’s there to do her job, not to meet potential dates. Part of her job may be to be friendly and accommodating to customers, so she may not feel free to respond as she otherwise would.

As another example, suppose you express interest in someone who works for you. The power imbalance between an employer and an employee can create pressure, even if you have no intention of doing so. She may worry about how declining your invitation could affect her job or your working relationship.

Or consider approaching someone in a deserted parking garage late at night. Even if you have no such intention, she may still feel unsafe or threatened.

The point is that it’s not enough to consider your own intentions. You also need to consider the circumstances and how they might affect the other person’s experience. Being attuned to someone means recognizing when the context itself might make an expression of interest unwelcome, regardless of how openly and respectfully you communicate it.

Taking the First Step

I’ve been telling you that you need to be willing to take a risk and also to be able to hear a negative response with respect and gratitude. But what if you can’t do one or both of these? If that’s the case, you are not alone. Plenty of men have had past experiences that were so discouraging that they have become too afraid, paralyzed, or otherwise unable to take this kind of risk. If you don’t have a baseline sense of your own value, you may not be able to hear a “no” without taking it personally and getting reactive. If either of these is the case for you, there are opportunities to develop and practice these skills in supportive environments, including, for starters, the following three.

• Dating and Relationship Coaching. One option is to work with a coach who’s been in that place in the past and overcome it. I can help you to do the same.
• Professional Cuddle Therapy. A Cuddlist-certified professional cuddler is a trained professional who provides a safe, low-risk environment for you to practice expressing desires, making requests, and being present to the response of another in the context of platonic touch.
• Surrogate Partner Therapy (SPT). SPT provides you with the chance to learn, not just intellectually but in an embodied way through participation and practice, everything it takes to create and sustain mutually enjoyable intimate relationships.

These approaches differ, but each can provide opportunities to develop greater comfort with your desires, practice making requests, become more attuned to others, and learn that hearing no doesn’t have to be devastating.

The goal isn’t to become someone who never feels afraid. It’s to become someone who can feel afraid, express a desire anyway, and remain present and respectful regardless of the response.

You don’t have to stop wanting what you want. You don’t have to hide your desires, apologize for having them, or pretend you don’t care. You can want something deeply and express that desire openly. And you can do so while honoring another person’s freedom to want something different.

That takes courage. It takes vulnerability. And it creates the possibility of something far more satisfying than getting someone to say yes: a connection in which both people genuinely want to be there.