Sex-Positive Etiquette for Men: Discussion Recap

By Kendra Holliday | May 5, 2020

On January 27, 2019, my not-for-profit local community organization Sex Postive St. Louis held a Sex-Positive Etiquette for Men discussion at Shameless Grounds.

Here’s the event description:

This event is free and open to all SEX+STL members.

Men – do you wish we had more female members? (Note: as of right now we have more than 4300 members on our Meetup group. I’m guessing it’s ~ 60% men, 40% women.)

Do you wish women were as fired up to get some action as you are?

When you attend our clothing optional events, is it important to you that there’s a decent number of women there?

Do you want to touch and be intimate with women?

Do you ever wonder how to best approach women? Are you successful in your dating endeavors?

Join us as we discuss sex-positive etiquette for men. We’ll give some examples of how NOT to interact with women online, and constructive suggestions on what works better. If you have questions, we have answers!

Please come if you would like to be more successful dating and hooking up with women. Come if you are a woman and want to share your experiences and preferences. Come if you are a man who is successful dating women and have some insight to share. Let’s all learn together and create a truly sex-positive space for everyone!

The reason why we hosted this event is because our female members informed us that they were being contacted by male members with inappropriate messages.

We have a member harassment policy in place. In addition, I made this quick video reminding men that our group is not intended as a dating or hookup site.

Here are examples of approaches that can be perceived as inappropriate:

  • Sending members you don’t know a message that you’re looking for sex.
  • Attending a happy hour and asking the women there if they will kiss any random man on the street.
  • Posting on the discussion board that we should host a penis size contest and make sure there are sexy ladies on hand to judge it.

When women get bombarded with strong questions and messages like that, it turns them off and drives them away.

If there’s one big takeaway message from our discussion, it’s the following:

When approaching women, don’t come on too hot or too strong.


I regard creepiness as pushing boundaries and personal space too soon – eagerness and lack of social awareness makes this behavior repelling, instead of compelling.

Let’s take the old chicken or egg dilemma. Guess what? The egg came first, and women represent the egg. Men – you came out of an egg. Don’t peck the egg to death when you’re trying to get back in.

We’ve all experienced abuse and trauma, but men should assume that women have experienced about four times the abuse and trauma as a man. Women are more likely to be victims of abuse and violence. Women have to do more emotional labor.

So when you come at a women wanting things, you need to know that they have already been hit up five times that day, and are already even more depleted than you are.

Instead of making big asks right off the bat, come at women with a “what can I do for you?” attitude, so that they feel comfortable. After all, you want to energize her, not drain her.

Once a woman feels comfortable and valued as a human being, THEN you can get freaky later on.

I always maintain that if women are happy and healthy in our society, then men and children will follow suit.

If this concept bugs the shit out of you and you resent having to change your approach, then I can guarantee you will continue to sabotage yourself. You have to change your approach if you want better results.

Being pushy, entitled, and dishonest will only drive women further away from you.

We recorded the discussion for those who couldn’t attend. It’s two hours long, and the first 30 minutes  is slow and awkward, so I will summarize key points below in case you would rather read about it or have difficulty hearing it.

Sex Positive St. Louis has tried to come up with a formula for keeping women’s comfort and safety a top priority – several times a year, we host public happy hours, private, women only events, and other miscellaneous, mixed events. This allows women to build confidence in safe spaces.

Our group is successful because it is moderated and we have a member harassment policy in place. Three of our five co-leaders are women.

We offer a unique combination of educational and entertaining events so there’s room to learn as well as just have fun. Our group is NOT meant to be a dating or hookup site. It’s intention is to allow people to meet like-minded people and make friends, so that if you are PATIENT and attend more than one event, you will run into familiar faces and develop meaningful relationships. However, if all you do is post on our discussion board and never attend events or just try one and get frustrated, what do you expect?

How do you make someone feel comfortable? Treat them like a human being. Don’t be greedy, eager, desperate, immature, intense, or act like you want to get her alone immediately. Invest time in developing relationships. Don’t try to dial it in, unless you’re hiring someone for a sexual service, and even then, realize that you’re engaging with a person, not ordering a pizza. Don’t fetishize/objectify people for specific body parts.

Recognize that women have different safety concerns. Be sensitive to where they are coming from – women have more to lose when it comes to pregnancy, STI’s, their life – so we have to be more selective and intuitive.

Be yourself – if you aren’t a perfect human being (who is?!), then promote your quirks or skills. Think about your energy and what you have to offer. What do you bring to the table? (See this excellent article: 6 Harsh Truths That Will Make You a Better Person.)

How do you come at someone to put them at ease instead of offended? When contacting a woman on online dating sites, be brief, polite, and respectful. Send them a short message introducing yourself, and give her indication you have read her profile and share something in common with her. Close out your note with a question.

Another big takeaway is to be authentic and honest. It’s fine if what you want is casual sex or to explore a specific kink. But don’t let that be your opening line. Wait until the second or third time you’ve spent time with each other to bring that up.

Communicate clearly and respectfully. Tell her that you would like to discuss relationship goals, sexual interests, health status, but you don’t want to put her on the spot, so she should let you know when she is ready to have that conversation. Allow her time to process and proceed on her own terms.

Slow and steady wins the race. The men I know who are most successful with women and sexually fulfilled are men who have not rushed, pressured, or manipulated women. Added bonus: When you let things unfold organically, you don’t have to worry about being accused of sexual assault! For example, if you’re on a date with a woman and it’s getting late/she’s getting drunk, tell her you would love to be with her sometime, but tonight is not the night.

Be realistic with your expectations. Better yet, don’t have expectations. Learn to enjoy the moment for what it is, instead of plotting next moves and wondering what else you can get.

NEVER ghost someone. It’s okay to tell someone why you don’t want to see them anymore. It’s better to be upfront than leave them hanging and wondering.

Notes from a polyamorous male member in relationships with three women:
Women think differently than you.
Women have different hormone levels than you.
Women can detect your “VIBE”, the energy you put out and around you.
Women can detect if you are a “caring” person or just trying to manipulate them.
By and large, women don’t really care about how flashy you are, they care more about what is in your heart.
Women are not stupid! Don’t expect to pull something over on them.
Women care about clean, brush teeth, use mouthwash, don’t be slovenly.
Women want to be comfortable around you and not have to be on their guard for bad behavior from you.
Being confident is NOT being entitled, demeaning, or disrespectful to others.

Things to disregard when it comes to interacting with women:
Everything you have seen in porn movies.
Advice from pickup artists.
Any ideas about getting women to do what YOU want.
Being funny all the time. Having a sense of humor is important, but you don’t want to be the court jester – it comes off as insecure.

Genuinely show care for others and their life troubles.
Show genuine empathy to others.
Ask questions and listen.
Shed all vestiges of entitlement. You are not entitled, you have to earn trust in others.
Accept others for who they are – including yourself. Cultivate confidence and self-love.

As a direct contradiction to what was stated above (“Women think differently than you”) perhaps it’s better to focus on the things that make us similar, instead of different. We all want the same thing – intimacy and connection.

Some great resources: A book on mature masculine archetypes, King, Warrior, Magician, Lover.

Dan Savage’s podcast, Savage Lovecast

Paging Dr. Nerdlove website and podcast

Please share this post with anyone who might benefit from it. It is a dynamic document, so let me know your feedback and I will update it.

If you want more guidance, you can consult with the sex-positive counselors listed on SEX+STL’s Links page. We will also be offering a more intimate (smaller and private) class that goes into more detail. Stay tuned!


Chris 2019-02-11 12:07:04

Excellent advice. I wondered about the mid-posting assertion that women have more to lose than men do from contracting STIs. Yes, it’s true, as the CDC confirms:

“Wonder, rather than doubt, is the root of knowledge.” (Abraham Joshua Heschel)

Thank you, Kendra, for the knowledge, reminders about behavior, and for instilling wonder.


    Kendra Holliday 2019-02-12 08:52:37

    Thank you for this CDC link! A vagina is like a tidal pool, a receptacle that is susceptible to microtears from friction. This is why it’s important to wash up after sex, even when you use condoms.


Mat 2019-04-06 14:04:08

Is/will this be an annual event? I would hope that as we better ourselves, more men would be willing to learn/share. I know I’d love to make it to one for this reason.


    Kendra Holliday 2019-04-06 16:02:10

    We host these as often as we can, which is usually every other year or so. Each one is different! Definitely one of our topics in reg rotation.


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