Being Bold

I get a lot of questions from men who want to be able to approach women and aren’t sure how to do it. Whether they’re interested in socializing, dating, or a sexual connection (not that those are mutually exclusive), there are plenty of guys who would like to do engage with women without being creepy, but they don’t know how.

The common advice for men tells us that we’re supposed to be aggressive towards women. One big problem with that is that aggression is much more likely to cross someone’s boundaries, or insult them, or disrespect them. Aggression can easily go too far because it’s often uncontained. And even if you don’t think that your aggression is out of your control, most people have experienced uncontained aggression hurled at them at some point. So while you might be managing your aggression just fine, there’s no way for anyone else to know that in the moment. That’s especially true for the many women who have experienced sexual intrusion and assault. Expecting women to take it on faith that your aggression is somehow different from those other guys’ is simply unreasonable.

It’s a tricky situation for men who are aware of the these things. There aren’t many role models for how to navigate your way through this, which is one reason lots of these guys end up squashing their sexual desire and attraction. Men who care about these issues are worried they’ll cross a line. I’ve heard lots of men tell me that they don’t know how to express their masculinity without being dicks about it, so they shut it down. Others are worried that they’ll be accused of being creepy or committing assault. And a lot of the time, they get trapped in the other side of the double-bind because then they’re told that they’re being wimps because they aren’t initiating anything. That firmly puts them outside the Act Like A Man Box and makes it impossible for them to win.

Of course, this isn’t limited to male-female dynamics, and I’ve heard similar concerns from people of many genders and sexual orientations. In fact, when I teach How to Not Be “That Guy”, the workshop that Alex Morgan & I developed, there are often as many women as men. But there are far more social, cultural, and structural systems that reinforce these patterns for men who want to approach women, especially cisgender men. So while I believe that everyone needs to learn better sexual and relationship communication, I want to focus on the group that I think needs it the most.

Fortunately, there’s an easy way to deal with all of this. It’s entirely possible to approach someone and be confident that you won’t go too far. What you need is an enticing invitation. Here’s my formula:

Step 1: Start off with an “if statement” such as:

  • If you’re available…
  • If you’re in the mood…
  • If you’re into it…

Step 2: Follow with a statement of your desire

  • I would like to go out to dinner with you.
  • I’d enjoy kissing you.
  • I’d love to spend the night with you.

Obviously, the details need to be tailored to the circumstances and the specific people, and it’s all too easy to go past the line. But the basics of the formula can be applied to lots of situations.

These sorts of invitations make it clear that the desire is only there if the other person is into it. If you aren’t available, then I don’t want to go out to dinner with you. If you aren’t in the mood, then I wouldn’t enjoy kissing you. It’s implicit that the desire is present if (and only if) the other person’s consent, interest, and availability are present. That demonstrates a high level of care and respect, and it makes a difference. Here’s why.

Consider these two statements:

  • If you’re in the mood, I’d like to kiss you.
  • I’d like to kiss you, if you’re in the mood.

From a logical perspective, these sentences are saying the same thing. But from an emotional perspective, they’re worlds apart. In the second version, if the other person has any defensive reaction, it’ll be harder for them to hear the “if statement.” It’s important to start by making it clear that you don’t want to cross their lines. Demonstrating your respect gives you much more room to be bold.

Respectfully telling someone that you’d like to dance with them, or kiss them, or have sex with them, or go out for a drink with them is a bold act. Owning and naming your desire is bold. Allowing yourself to be vulnerable when you have no idea how they’ll respond is bold. Making a move like that is bold. And that is really sexy. I’ve had a lot of women tell me that if a guy could do that with them, they would find it really attractive.

The trick is to do it in a way that clearly shows that you can contain your desire because that’s what keeps the boldness from sliding into aggression. Rather than squashing your desire, being bold lets you fill up your space without spilling out onto someone else. That’s the balance than we need to find.

Being bold makes it easier to be open to whatever response the other person might have. When you offer the invitation without being intrusive, their answer doesn’t need to push you back. Since you’ve invited them to step forward, rather than rushing past their comfort zone, they have more room to respond. That creates more safety, which makes it more likely they’ll want to say yes. And if they do decline your invitation, they can be more gracious and kind about it, which is much easier to receive. You’ll be more able to see their reply as declining an invitation rather than as a rejection of you. And that makes you far more able to thank them for letting you know and move on.

Protip: if someone says “no,” thank them for their honesty. Not only does it keep you from looking like a jerk, you’ll enhance your social reputation. Women are much more likely to talk with each other about their experiences with men than many men realize. Building a reputation as a guy who can handle it when someone declines your offer will go a long way.

Of course, being bold only works when the invitation is genuine. If you use it as a line that you try on every woman at a party, it’s not going to work because you aren’t actually trying to connect with someone as a person. And being bold also only works when you’re not pushing for a particular response. If you don’t give someone the room to say no without repercussions or pressure, then you’re doing it wrong. And lastly, this formula is a guideline, not a script. You need to customize it for each situation and for each person.

From talking with guys, I think there’s a lot of potential in shifting how we think about aggression. Being bold is a much better way to frame it because it helps us remember that we need to be aware of other people’s boundaries and comfort zones. So now, when I hear people say things like “women want men to be aggressive,” I take that as an opportunity to shift things. Most of the time, what they’re really trying to say is that women want men to be bold. When it comes down to it, boldness is much sexier. Try it and see for yourself.