How Gender Stereotypes Hurt Your Chance of Finding Love


There’s all kinds of gender and sex-informed rules for dating - and if you’re still following them, you may be single because of it. Even if you don’t think you’re still following them because you’re in “conscious” community - you might be...unconsciously. Below are some partial descriptions of some of the people we’ve worked with over the years in our dating coaching and matchmaking business. Here’s a quick pop quiz for you: Go through the descriptions and guess the person’s gender and sex as quickly as you can. Make sure that you cover up the Gender/Sex column.

The options are Transgender Male, Transgender Female, Cysgender Male, Cysgender Female. FYI - Cysgender means the person identifies with the sex they were assigned at birth. Transgender means the person does not identify with the sex they were assigned at birth. For example, a person we’ve worked with was assigned a male sex at birth and identifies with the female gender - so they’d be considered a transgender female.

Statement the Person Made Gender/Sex

“I like to get dressed up in a skirt and heels a few times a week just because it feels good.”transgender male

“I’m very math and science-minded, which makes it difficult to relate to potential partners.”cysgender female

“I feel like I don’t have enough energy to meet the sexual needs of a partner.”cysgender male

“Ever since childhood I have obsessed over having a dream wedding and kids.”cysgender male

“I feel like I don’t have enough energy to meet the sexual needs of a partner.”cysgender male

“I love to go out dancing with friends and want a partner who likes to dance.”cysgender male

“I cannot multi-task for the life of me.”cysgender female

“I don’t have any kind of sex trauma - and I don’t really like sex.”cysgender male

“I’ve had body image issues and eating disorders throughout my whole life.”cysgender male

“I’m very wishy-washy and have a hard time making decisions.”cysgender male

“I’m a full-time parent.”cysgender male

“I tend to go all-in with new relationships, claiming that they’re ‘the one’ very early on.”cysgender male

“I don't want to be constantly processing things and talking about feelings.”cysgender female

“I don’t want to have kids.”cysgender female

“My partner has childhood sexual trauma, and I don't know how to help them feel more comfortable in bed with me.”cysgender female

“I climax too quickly for most partners.”cysgender female

“I’m getting facial resurfacing treatments to look younger.”cysgender male

“I work as an auto-mechanic, am married to a woman, and am the mother of three.”transgender female

“I like to have multiple partners.”cysgender female

Did your guesses match up? Did you notice any biases?

The reason I'm writing this article is because we’ve found that many people who hold stereotypes about men and women have a hard time starting relationships and/or maintaining them. And one reason for that is that they are not considering their partner or themselves in their unique wholeness.

They have a preconceived notion of how each sex acts, thinks, and feels - and in turn, create or follow rules in courtship as if that will better their chances. Some of these notions are conditioned into our psyche from family and cultural messages. And some of these notions come from more evolutionary and science and biology-based explanations.

No matter where they come from, I feel that they are VERY unhelpful when it comes to attracting and maintaining relationships [not just romantic relationships, either. If you're starting to read this and are already thinking: "Spiritual bypass, Kendra!" - please do not mistake what I'm saying as "Men and women are the same / equal." I am not saying that. I am not denying institutional oppression. And I am not denying the differences that have evolved because of it. It is in part my acknowledgement OF these differences and institutional oppression why I write this].

For me personally, what I thought it meant to be a woman impacted my past relationships in many negative ways. In bed, I thought I needed to be a certain way. I thought there was something wrong with me for not wanting to have kids. When it came to “that time of the month,” I was always blaming my sensitivity or moodiness on it [side note: Hormones and mood changes in women with menstruation is a GREAT example of where the issues of institutionalized oppression and some of my points meet. Men have hormone changes throughout the month too! Helloooooooo???!!!! There's a GREAT TedTalk on the intergenerational transmission of the whole "PMS" story in American culture here]. The amount and way I ate food was always something I felt was inappropriate for being a girl. Those are just a few examples - but these seemingly little rules and expectations I adopted really fucked me up in some pretty big ways in relationship. After working as a psychotherapist and coach with people, I realize I am definitely not the only one - that many of our single clients have had this masculine/feminine, gender/sex stereotype thing preventing them from being themselves.

How stereotyping kept Lesa and Marco single Lesa had always dreamed of getting married and having children. And at her age, she started to fear that it might not happen. In her dating life, she would steer clear from having any conversations of wanting marriage and children. She thought that men would start feeling trapped because most men fear commitment and settling down. Date after date she would withhold this huge part of her vision. Her longest “relationships” were just a handful of dates. Little did she know, we were working with Marco whose biggest dream was the same as hers.

In session, he asked us “What’s off-limits conversation on a date?” We told him that if you’re truly being present and speaking from the heart, there are no off-limits conversations. On his first date with Lesa and in the flow of the conversation, he asked her about her thoughts on marriage and children. She was absolutely shocked! She couldn’t believe a man was asking her. But soon she was able to exhale as they both shared their very similar vision for family. They became charged up, smiling, and inspired just talking about it together.

Fast forward to today - they are married and pregnant!

Had Marco assumed that a first date was limited to conversations about work and hobbies, and had Lesa chosen to withhold her desire for a family so she wouldn’t scare the guy off - they may still be single now. Instead, they were able to practice being in the moment with each other, following the natural rhythm of their conversation [rather than holding tension to avoid certain topics], and were able to see in the first date that they could be a match!

How stereotyping kept Adrian and Casey single Casey had read many magazines, books, and even got individual coaching from another dating expert on how to be attractive to men. In the first coaching session with us, we found out Casey’s current approach: If you’re dating someone you really like, don’t answer their calls or texts right away - wait a few days. It will make them want you more.

We told Casey that most people tend towards one of these categories in relationship: fear of abandonment, fear of inundation, or a mix of the two. “Fear of abandonment” sounds pretty negative - but really it’s just a healthy need for connection. Likewise, “fear of inundation” is just a healthy need for space.

A person’s need for connection or space is usually related to their attachment style, something that’s formed as a result of their childhood caregiver relationship [we won’t go into the details in this article, but it’s definitely something worth reading about for easier relationships].

The point of this was to explain to Casey that since every person’s need for connection or space is different, it’s important to simply ask the individual about it. For someone who needs space - it might be a turnoff to get rapid fire texts the morning after hanging out. For someone who needs connection - it might have them totally turned on, giddy, and bantering back and forth for hours.

After Casey’s third date with Adrian, it was clear they were diggin’ each other. So, Casey told Adrian, “I would love to be in touch at some point every day even if we don’t get together, but I definitely don’t want to cramp your style.” This allowed Adrian to think about it and say, “Yeah, I think seeing each other everyday would be a lot for me at this point - but it would feel good to connect in some way everyday, whether it’s texting or a phone call. It feels good to know you’re thinking about me when we’re not together!” Adrian also was especially turned on by the vulnerability, upfront communication, and genuine interest in his needs.

If Casey had continued to play the game of “hard-to-get” or whatever, Adrian could have questioned if this person was reliable, considerate, and had mutual feelings.

Here’s a short list of some other gender and sex-informed assumptions in dating:

The man should pay for the date. The man should pay for most things. The man should make more money than the woman. If anyone in the relationship, it’s the man who wants to be polyamorous. If there’s an age difference, it should be the man who is older. The man should instigate most plans. The man should reach out after the first date, but wait a few days. The man doesn’t want to talk about feelings.

Men should be more masculine - in bed, in communication, with money, etc.

The woman should not talk about big things like marriage or kids early on. The woman should allow the man to pursue - especially after a first date. The woman wants to get married. The woman wants to have kids. The woman is only dating one person at a time. The woman always wants to talk about feelings and process things. The woman should wear makeup, do their hair, and wear dresses or something “flirty” or “sexy.” The woman should eat like a bird and not finish the meal.

Women should be more feminine - in bed, in communication, with money, etc.

News flash: Gender roles are blurring more and more. Between growing equal rights, more education and acceptance of diversity in sexuality and gender, more people realizing and coming out with the fact that they do not fit in a binary, diversity in media representations [shows like Modern Family, Transparent and Frankie & Grace - I mean...they're trying], marriage equality, diversity in family makeup [be it LGBTQ parents, single parents, 3+ parents, etc].

All of these things are contributing to more diversity within American family structures. And more diversity in family structures means that the modeling of “traditional” roles to children and others living amongst them SHIFTS.

But if we keep arguing the same old points over and over - it makes the shift a lot slooooooower.

Some people argue: But there’s DNA! Hormones! Genetics! Evolutionary science! Each proves the tendency toward traditional roles of “man” and “woman.” OK, that’s totally valid and WAS probably true at some point - hunters vs. gatherers, making babies vs. taking care of babies, protecting vs. nurturing, etc. I totally get that. But in modern day - there’s absolutely no way to prove that these “tendencies” are still the case. You’d literally have to study every single human on the planet. Our survival isn't dependent on maintaining these separated tendencies anymore - so they can and DO exist in anyone in varying amounts and in varying aspects of their lives. Second - even if you were able to study every single human, the newest science about genes shows that our DNA doesn’t just get billions of years of evolution passed on. On an epigenetic level, our genes are reacting to present day experience and are inherited generation to generation.

Let's put it in a living example. Since my grandmother’s genes were subjected to certain stereotypes and even traumas of her time, she COULD have passed them onto my mother, and she COULD have passed them onto me. This is regardless of billions of years of hardwiring. If, say, my grandmother grew up in a household in which all her siblings were treated as individuals rather than by gender/sex [i.e. given household and farm tasks, spoken to the same regardless of sex, encouraged to dress and act as they like, etc.], then whether she came out more “masculine” or “feminine” would be totally unpredictable. She’d have mixed up qualities and would pass those down to my mother who would pass them down to me. But even that’s not guaranteed. Maybe my mother picked up on her father’s story of women and then passed that down to me. Maybe I rebelled against it, and only some of it got passed on. PHEW!

See how there’s just way too many factors that can influence us?

If this is the case - and I’m sure it is - then that means that all of us have a little bit of everything going on. And it’s pointless to argue about which is more prevalent - evolution, conditioning, epigenetics, on and on. Each person is a fucking individual and needs to be treated as such.

I think one of the biggest and most insidious preservers of the stereotype problem are these two words: “masculine” and “feminine.” They’re especially sneaky because most people in conscious community would say, “Oh, but when I say masculine or feminine, I don’t mean man or woman. They’re just a set of qualities.”

Yeah, they might just be a set of qualities - but I’d say about 99.999999% of people still hear “manly” or “womanly” no matter how inclusive or spiritual or conscious they are. [Side note: What’s funny to me is that we could use literally any word to encapsulate the set of qualities for "masculine" or "feminine." For instance, we could use the word “flippibitikibble” for masculine energy and “quabiskillibop” for feminine energy, and it would probably help somewhat.]

While some aspects of the “masculine” and “feminine” energies may have evolved for the survival and propagation of the human species within men and women respectively at some point, I believe that we have evolved beyond them [I mean - just the fact that people don't necessarily identify as man or woman proves that]. I believe that now we have mastered survival and propagation in many ways, and the next call to evolve is for the human species to THRIVE as one large organism [maybe called “humanity”]. It is diversity working in harmony - not conformity - that sustains an organism. Just look at the biology that makes up any organism and see the diversity within - all of which are beautifully and peacefully symbiotic.

Yes, there’s still lots of separation, exclusion, discrimination, and other dissing words that end with “ion” in the world. Despite that - and probably even BECAUSE of that - I still somehow sense a real and growing feeling of oneness throughout the planet. [I mean, for one example just look at the internet. Learning about each other and connecting heart to heart is no longer limited by geography. And I really only see it getting better and better from here...even if there's contrast and trauma and shitty things that happen along the way. It's part of it.].

I started writing this with the theory that some people are still single because they’re holding onto unhelpful stereotypes and generalizations about sex and gender. But I'm not gonna just bitch about it without sharing some ideas on how to shift it. Here’s the “new rules” [not really rules...just ideas] I’m proposing for dating and maintaining a relationship:

1. I usually don’t like to be so blunt. I typically like to use wording like: “I invite you.” But I’m gonna be more direct here and just say it: Stop using the words “masculine” and “feminine”!!!!

Just use the words you actually mean, like “direct” [like I just did] or “assertive” or “focus” or “dominant.” Just use words like “flow” or “receptive” or “surrender.” I feel that the sooner we start using the actual words rather than the umbrella words, the sooner we’ll be able to unravel “masculine” from men and “feminine” from women.

Don’t worry - you can still describe what you’re talking about, I promise [which might be particularly important for those in conscious community who are therapists, workshop leaders, tantra teachers. You could have a huge impact on this! Alas - my feelings are the be all end all].

2. Again, I’ll be direct: Stop using the wording “most men” or “most women.”

I used to think, “Oh, good. That person is at least being mindful and trying to acknowledge that it’s not ‘all’.”

But saying “most” isn’t enough to unravel the depth of this issue. Again, the sooner we stop saying “most,” the sooner we start acknowledging the individual...and the TRUTH.

A friend of mine asked me once: “How would you feel if I said, ‘In my experience, most men…’ or ‘In my experience, most women....’?” I think that’s a great improvement. But it’s still not good enough to me because it’s still keeping your story of men/women alive [which may not be an old, unhelpful story for you].

Maybe you could literally say, “From my experience I have developed the story that many men are like this or many women are like that…” I know it’s wordy and clunky but at least then you’re naming that it’s a story, which gives a little more space between you and it [giving you more a chance to release it, if it’s been holding you back - which I’m sure it is].

3. Just fucking ask. Remember that expression: “Assume = Making an “ass” out of “u” and me” or something. I don’t know, it’s something like that.

Lots of our clients say they fear that if they ask it’ll ruin the romance or the moment. Well, if you’re looking for conscious, deep, honest connection - getting asked or asking would likely just heighten it.

Genuine curiosity is part of the cure for SO many things in relationship.

Examples: “Hey, I’d love to pay for this meal - how’s that feel for you?” “I’m playing with being more in the receptive mode… I wonder if you’d be open to planning our next date?” “It would feel good to me to be in touch a little throughout the week. What would feel good to you?”

Once you’ve asked the question, then you can negotiate from there.

The other day one of our clients was talking about how she’s dating someone who does not make as much money as she does, which she’s fine with, in theory. However, in practice, she says she still wants him to pay for more things. “I just grew up getting the message that men should pay for things, support me, and that’s part of courting, so it’s hard for me to be OK with it.” I encouraged her to just tell him that and to tell him that she knows that’s her own shit to clear. She ended up telling him, which allowed a huge amount of tension on both their ends to release. They also set an intention to start creating free and low-cost romantic time together.

4. Be yourself. Whether you fit a traditional gender role or not - be yourself. Being yourself is the easiest, quickest, built-in filtering system for finding a partner. I can’t tell you how many people withhold being themselves in the beginning for fear that they’ll be rejected. And I’m like GOOD! Get “rejected”! Being someone else is not sustainable and feels like shit. So, knock it off! J/K... I love you.

Something that I learned at Naropa University from my studies in Dance/Movement therapy is that having a wide repertoire for movement and expression helps us to feel more integrated, allows us to empathize with a range of other people, fosters emotional and relational intelligence, giving us more flexibility and resilience, opens up new opportunities for knowing yourself - the list goes on. Ok, so I cognitively understood all this in school and thought it sounded cool, but 5 years of consistent practice has allowed me an embodied experience of it. I now hold a value of continuing to expand my expressive repertoire. As it pertains to this article, I intentionally practice and play within the linear, heavy, grounded, and fast movements and also the flowing, light, ethereal, and slow movements [Look! I described masculine and feminine without having to use those words! Does that feel more inclusive to you? does to me!]

Sometimes conditioning and unconscious patterns get stuck to us without us noticing. So, some of the things that you think are yourself might need a little attention and updating. For instance, our client Cathy was self-described as “too masculine.” She was very driven, focussed on doing, and liked to have things planned. We coached her with expanding her expressive repertoire by practicing to be in a feeling state, focussed on being and receiving. It was very important that the intention here was not for her to change and become more “feminine” because that would be more attractive. The intention was to experience something new, to let go of her parents’ “must be productive” attitude. From this she’s decided to continue integrating the feeling, being, receiving way into the parts of her day where it feels good. As a result, she says she feels like she’s able to be more of herself.

Expanding your expressive repertoire can also help anyone out there reading this who’s like: “But I’m only attracted to women who are feminine” or “i’m only attracted to men who are masculine.”

Well, claiming an “only” is a pretty rigid, limiting belief first of all. And second - by expanding your own expressive repertoire, it can allow you to become attracted to a wider range of people.

If you feel like you want to practice really being yourself - we wrote a handy 5 step process for it in this article because this comes up in almost every group I run. I know it sounds a little weird to read an article on how to be yourself. It seems like that should be the most natural thing EVER. But some of us are so used to fitting molds or seeking approval that we’ve lost ourselves. All it takes is a little practice - plus, it’s really fun! [Read more here].

5. Own your projections. Consider the partner you’re wanting to call in - man or woman. Take a piece of paper and fold it into three columns. Make a list of 5 assumptions you have about all or most of them. Next to the assumption, boil that assumption down to one word if it’s not already by answering the question: What does it mean about this person that they’re like that?” Then go through the list and ask yourself - how am I like this or how have I been like this in the past?

My assumptions about Men -Which means they are...How am I that way? or How do I not let myself be that way?

Men don't remember important things.carelessI can be careless too.

Men never do housework.lazyI can be lazy too.

Men only think about me in a sexual way.hypersexualI can be hypersexual too.


Even saying “most men are _____ [slobs, don’t know how to express emotions, don’t notice things]” is harmful because it does not acknowledge your part in it. My invitation is when you notice yourself wanting to say “most men this” or “most women that” - try saying “I’ve tended to attract men who are like this” or “I’ve tended to attract women who are like that.” This kind of phrasing may help remind you to be curious about yourself. You might ask yourself: What’s in my vibration that would attract men who are lazy? You might do a little shadow work with yourself and ask: How am I lazy? Or How do I deny myself the ability to be lazy? Maybe even try owning that which you are judging in the other by saying: “I am lazy.”

I’ve seen magical things happen in my own life and that of my clients when they start to own their projections. I can’t tell you how many people have done this work and within just a few weeks, they meet their match. This is because - we don’t attract who we want, we attract who we are.

After working with hundreds of people, I can honestly say that we’ve heard there’s just as many “flakey” men as there are women. There’s just as many “incapable of expressing themselves” men as there are women. There’s just as many “scared of commitment” men as there are women. I could go on all day here. And if you’re still thinking - no way, it’s not possible - I urge you to check out “Rule No. 3” and own that shit!

Well, this certainly has a lot in it. But I’m super duper passionate about it. I really envision a world where diversity is the new norm - and untangling our concepts of gender is definitely a huuuuuuuge part of it.

Having said that - will you please give me your feedback? I’d love to hear what YOU think about any or all of this. Because of course, your opinion - even if it’s wildly different from mine - is awesome and VERY important to me and this issue. I am still learning.

And for those reading who are single - let me know if you try any of this out and how it helps or hinders your love life.

And now I exhale. Thanks for taking the time.