When Prince Charming Becomes the Toad

Your prince charming can very likely become the toad if you don't watch yourself.

I don’t know a woman who can separate sex from love - IF SHE IS IN TO HIM. Lots of women will claim they can, but it’s mostly bullsh*t. Maybe some women can. But I don't know them. Yes, I know it’s POSSIBLE to have sex with someone you’re not that into, and not get attached. But that poor guy is just going to be dissed for the other guy who triggers every oxytocin hormone in your blood, and then it’s history.

Boys, guys, men - most CAN separate love and sex. They can have sex with you, enjoy their sexy time with you, but stay unattached. It’s a biological fact. Do men ever get attached? Of course they do. They need and crave love as much as you do. But they can sleep with you and not be tricked into thinking there’s more to it. It can be just sex.

I was able to separate love and sex once. In my 20s. He was one of the sweetest boys I had ever met, and he was crazy about me. I just wasn't crazy about him. NOT because he was sweet, but because there wasn't much more to him than sweet. I had fun with him, but I was just never going to fall in love. I was able to occasionally be intimate with him and not become emotionally involved. Admittedly, it was kinda cool to feel like the “guy” because naively I thought that gave me power. It may have given me control, but there's nothing powerful about a heart that craves deep emotional connection that settles for “nice” hook ups. Besides, what I really needed was to feel inspired to relinquish control. It really just comes down to that, doesn't it?

I ended things with sweet boy for someone really, really toxic. He was older - by almost 10 years. He looked very mature… manly. He also was very smart and charming. He made me feel amazing - in the beginning. He soon became mean as hell. I entered that relationship thinking I was a confident, strong young woman, but it turned out that although that woman was gestating, I definitely wasn’t close to giving birth to her yet. Instead, I was a girl who wanted love as much as anyone else, who believed in marriage and thought she was ready for it. But I barely had a sense of my worth, as I had very little idea of what was deeply important to me. I thought I had a high standard, but as it turned out, it was very, very low. I abandoned every part of myself in that relationship, and what I consequently experienced was soul-deep pain. I eventually had to come to terms with the fact that I allowed such ugly behavior, and that frankly, I still was in many ways a little girl afraid of her own shadow. I have no regrets though - I got the real ‘son-of-a-bitch phase’ out of my system, and I knew I would never visit the dark side like that again. And I didn’t. I successfully raised my standard a few notches.

When I was much younger - a junior in college, I started sleeping with this very cool senior from Greece named “A”. A was smart, athletic and nice enough. We had fantastic chemistry, and my heart and mind would race with anticipation at the prospect of seeing him Thursday nights at the local bar. But A and I had pretty much nothing in common. He was an avid snow boarder, and I kinda hated snow. I loved (and still do) deep, soulful conversations, and yet we had none of that. Just sex. He didn't try to be my boyfriend, even though he was very attentive when we were together. And as much as I tried to convince myself that I didn't need more - I didn't want more, I was in a weird, manic cycle: 

1. looking forward to seeing him (no texting in those days!!) eagerly hoping we would hook up.2

2. going home with him and being elated to be with him and get attention.

3. waking up the next morning high as a kite from the surges of hormones and neurotransmitters from being with him.

4. deflating in the afternoon. I would feel distinctly unfulfilled, empty and bored with everything around me… Classic come down.

I was attached. (mildly addicted?) Hooked to the idea of him, to the idea of being in a relationship with him. I was attached to being the object of his affection. Why?? Simply because I was VERY attracted to him and I was sleeping with him. He was a lovely enough human being, but he sure wasn't falling in love with me, and nor I with him. That’s lust for you.

No biggie - it was fun. I was young.

Fast forward many years: There was this gorgeous and insanely charming actor who used to frequent my yoga classes. I had watched him in an HBO series years prior, and had a huge crush on his character. Then there he was, flashing his wide smile at me every time he came to class. I kept it verrrrryy cool with him, but he pursued me hard for months. How could I NOT finally go out with him??? So I did. He was smart and nice and we actually connected. But the problem with ‘insanely gorgeous charming actor who’s HBO character I fell in love with + young me who hadn't fully grown into her own yet’ is this: My desire for his attention was disproportionately higher than my confidence in myself. Here and there I would sprinkle in the body language of someone too cool to give a fuck. I would share things about myself that were more about who I wished to be, rather than who I actually was. I don't want to misrepresent myself - I wasn't a total fraud, at all. I was me, just with a big slab of ego on the side. 

We dated a few more times, but if it weren’t for the fact that I was taken by the idea of him more than him, I probably would have ended it after date two. But I let it go on, unwilling to listen to the ever so brilliant yet often ignored voice of my gut that said, “he ain’t for you, Jillian.” *For those of you who date actors: remember, the characters they play on TV are not them.*

There’s more stories - like the guy I dated causally even though I wanted something more and was too afraid to say it. Then I said it, and it ended, and I actually regretted saying it!?? (wtf), Or the guy who I had amazing conversation with but felt very misaligned with sexually and yet I still wanted him to call me. (again, wtf?) To the amount of times I waited for a call or text from someone who I didn't even know well enough to warrant ANY of my anxious anticipation.

To be fair and honest, these tales are not the only ones of my rendezvous past. I have had lovely relationships as well, ones filled with authenticity and respect, even if they all had their expiration dates. I, and maybe you identify, so let me say we, can trace our relationship histories and find various forms of it: The healthy ones that devolved into more of friendship status, the toxic ones, the sweet ones that did nothing for us, and the ones we wish we never wasted our time on. Some were pleasant, some intense, and some were short lived ‘could-have-been-something-but-never-developed-into-anything' cycles of flirt and lust.

There’s nothing wrong with wanting someone you desire to desire you back. When I go back in time and scrutinize my attempts to find love, part of me thinks it was cute. They were all inevitable tales of my journey, and after all, the road to self discovery is lifelong. It takes maturity to identify our ambivalence towards ourselves and to finally accept whatever irresoluteness remains. Doing silly shit in relationships is part of growing up. But the challenge we all face is to use our discoveries to live in the light, and to embrace the perseverance that will be required of us to do so.

So, what about now? Are you over the age of 30, single, and trying to reconcile with your singleness? If you are, navigating dating, sex and love can be daunting, but it doesn't have to be. If you relate to anything I’ve written thus far, then you understand when I say that your navigation has to be different from how you operated in the past. You have to walk away from ever trying to make the guy you’re lusting for the “one”.  You must erase your secret wishes of being the one who he changes for, or of becoming the one who inspires his broken heart to love again. You have to discard the belief that he’s the only one.

So, what can - or better asked, how do we do it differently?

Know thyself:

As women, we are different than men when it comes to love, and I don't want you to ever feel like you have to toughen up and declare your independence from ever needing a man. I don't want you to ever feel ashamed of wanting a relationship, or for those moments when you feel acutely deprived of attention, praise, and touch. Part of feminine energy is to be a lover of love. We crave our own surrender, of letting go until we feel our softness again, until all the hard places in our bodies that’ve held our hurts finally decalcify, becoming wide open spaces ready to receive. It’s ok to long for your vulnerability. It is our greatest power, even though it’s foolishly devalued in our culture.

It really is OK. 

But what you must reject is: 

Pretending that it’s not ok. Convincing yourself that you don't need or desire to be moved - emotionally, physically, intellectually, and spiritually in this way. Going on dates and acting as if you don't want what you want by playing it cool because you think he won’t want you because you want what you want.

Which begs the question: why would you want him if he doesn't want what you want? Yes, your ego will be partially satiated (I say partially because the ego’s cup is never full - that is the nature of ego) if he shows interest. If you feel desired by him. But to be desired is NOT to be valued. If you lead with just your sexuality and ego when what you really want is true connection, you will suffer. You MAY get a “relationship”, but I assure you, it won’t have even close to the depth of what you need.

You do not need a man to be happy. 

But a good man, a man who you trust, who you laugh with, have fun with, share with, feel good around, will ENHANCE your life. Just as you will enhance his. He will elevate your emotions and feelings, as you will his. I can’t bullshit you anymore than I can bullshit myself: we as humans are better together, not apart. But: Your life can still be extremely fulfilling without a man. You can enjoy doing what you want to do when you want to do it as much as any single man does. You can acknowledge all the love that already exists around you and within you, and give it freely to your friends, family and community. You are not less than because you are single. There are many parts to you, and ‘the single and looking for love’ you is only ONE part of You. If you’ve been stuck in “single looking for love” you, give her a little breathing room. Take some time to explore and nurture your other parts and let the world, and the men you date see your other parts too.


“Rescuer syndrome”

I think every girl and woman has been somewhere on this spectrum at some point in her life. (Ps - Men DEFINITELY have this tendency as well - more on that in another post) Please don’t worry - almost none of us are immune, and it can be overcome. 

What are the symptoms of Rescuer Syndrome? note: even if you have merely experienced one of these symptoms, once in your life, it’s still something to acknowledge, investigate, and perhaps have a chuckle at.


  • You choose men who have A LOT of “work” to do on themselves. This could range anywhere from over-coming addiction and toxic relationships, to simply being “curious” about growth, without ever having done any real emotional or spiritual personal development.
  • You’re drawn to his “potential”: Even though he’s stuck in life and unmotivated to change, you stick around because you see so much in him.
  • You try, sometimes tirelessly, to nudge him forward towards this potential of his. 
  • You choose men who are going through a particularly dark time in their lives - such as a divorce or a death of a loved one. But you’re able to justify it, and believe he is ready for you.
  • You’re anxious in the relationship. You often try to manage the relationship and his life in an effort to control that which feels out of control: such as his moods, unpredictable behavior, or his general indecisiveness or non committal attitude in life. You start to feel like his mom, or his teacher or even the relationship’s manager.
  • He has a disturbing track record in relationships (cheating, lying, unable to open up, never had a relationship in his life that went past a few months) and yet, you find yourself justifying his behavior; after all, that was his past, and it will be different with YOU. 
  • You feel special and important that he wants YOU - especially because he doesn't open his heart very easily
  • You secretly believe that you will be the the one who inspires him to be a better man and fully commit.
  • You play the role of a spiritual teacher in your relationship: You want to help him, so you expose him as much as possible to all your practices such as yoga, meditation, eating well. You are the grounded force in his life, and give him advice. A LOT.
  • You’re constantly fearful that he will leave you. You often don’t feel secure, and don't entirely trust his ability to be in the relationship.
  • You’re extremely intuitive. You can actually feel other people’s potential, and it kills you to see them not reach it. You’re loving and nurturing and believe people should be given a chance. You also have an inner knowing when something is not right in your relationship, but have a very difficult time coming to terms with it. You just want it to be ok.

I really don't love the word “co-dependent”.  I think its overuse has blurred our understanding of it and let’s face it, to be associated with it is considered more than unfavorable. Despite it’s unsavoriness, however, some of it’s implications are intimately connected to rescuer syndrome, and I want to note - we all have been there, women and men alike, and it’s ok. NO shame. It does not mean one categorically lacks independence. For instance, and maybe you can relate - I’ve always been a very sensitive person - a sensitivity that made it difficult not to feel others pain - too acutely at times. Consequently, I frequently felt responsible for the (negative) emotional state of others, and so my energy was spent managing their states  - not out of compassion, but out of a desperate need to lift the burden I carried. This habit would show up rather amorphously over the years in some of my romantic relationships, manifesting in some form or the other of “rescuing”. 

Empathy is the willingness to give up our need to be right and instead place our minds in another’s heart. To voluntarily see the world through the filter of their beliefs and understandings is the biggest gift we can give to an intimate partner especially, because we will feel deeply challenged by their behavior at times. Empathy, therefore, is love.

It becomes our work then, to understand the huge difference between sharing someone’s pain and bearing it. It may be the most important work you do. And when you know this about yourself, it can, and should, inform how you choose partners. It does make a difference.

Sensitivity aside, I’ve also found that many women have core beliefs about men and love that are grossly limiting their potential. Beliefs that make them grasp anxiously to the wrong men -  FOR THEM. All of these beliefs share the same origin: SCARCITY. This deficiency perspective  always leads to poor decisions, since it is our nature to react to famine with fear. Yet it’s not entirely our fault, as we women have been partly conditioned by the cultural mentality to have these three limiting beliefs:

1. a good man is a rare and exotic breed of human. Especially in places like NYC and LA, where there are far more women than there are men. 

2. A strong connection with someone is also a rarity, and therefore, if we do have this connection, it means we’re supposed to be in relationship with this person.

3. A man’s heart is something to win - and that all other women are our competitors.

The great paradox is that evolution tells a different story than our conditioning. Our DNA is designed to make us selective. To choose the “fittest” who will be able to impregnate us, hunt well, and feed us. Although the modern woman may not want any of the above, we are in fact being selective all the time - with the guy who smiles at us on the street who we look away from, to our ignoring of a colleague’s flirtation. Guaranteed there is a man in your life that if given the opportunity, would love to love you. But THAT man you’re not attracted to, so you flex all your selective muscles with him, only to atrophy those same tissues when it comes to someone who turns you on. When you meet a guy who triggers you hormonally - when your oxytocin, estrogen and progesterone peak just at the thought of him, you must know that you’re in a potentially precarious situation. One where you’re at high risk of mistaking your lust for something deeper and more meaningful. This is why I ALWAYS tell my clients that if you’re really attracted, wait to sleep with him. Period. This isn't about him nor about playing games. This is about YOU. There are things we all must know about ourselves first, and fears we need to settle before we go there with a person.

This is some of the coaching advice I give to my single gals looking for love:

You need to know what you want.

If you want a relationship, which I’m assuming you do, you need to be able to say to yourself, and anyone else for that matter, that what you want is a meaningful, loving relationship. Put an end to your denial that maybe you don't want it, etc. If you DON’T want a relationship - I get that 100 percent, but I’m simply asking that you be honest with yourself and with those you date. Even if you genuinely aren’t looking for love, once you start sleeping causally with someone who you’re REALLY attracted to, that might confuse you. It might actually make you realize that what you really want is more. Not necessarily a bad thing.

Know who you want.

Too many people know who they want superficially - brown hair, medium build, nice, smart, funny, etc, but are afraid to really define what they want. They keep it “open”  and claim that all they want is someone kind and sexy and who listens to them… who understands them. This is all good. I want that too. But if what you want is lasting love, you have to get more comprehensive.

If you needed to hire a CEO for your company, are you gonna just keep it “open”? I doubt it. You would want to know A LOT about who this person is. What they stand for. Their psychology, attitude, values, communication style, beliefs, values - you name it. Their resume is only a part of the equation - you need to know if their nature  is in alignment with your company’s ethos. As adults, this is what we need to know about someone before we lose our minds over them and start a relationship.

Recently I took a walk with a friend who’ve I known for many years. This woman is a force - a few years ago, she decided to leave her job and pursue a dream - to create a product that would change the way people relate to their health, and feel in their bodies. As someone who had completely changed her lifestyle to support her personal wellbeing, she felt compelled to help others do the same. She had a vision. She was clear about what her product would be, and what it definitely would not be. And so, like a lioness chasing her kill, she didn't stop until she got it. Until her vision became a reality. During our walk, she was noticeably frustrated by the current state of her love life: “How could I have manifested so much in my career and I can't in my love life? I must be blocked.”

To which I responded very plainly: “Ya, you’re blocked - but not how you think. You’re too afraid to define what you want. Once you know, you’ll go for it - all you have to do is apply the same strategy you used in your career to your love life.”

My friend falls in the “I just want to be open” camp. Which, by the way, is a marked improvement from her decades long pattern of only dating one very specific archetype and refusing to explore more range. But she’s missing the clarity, the vision, the “I know what I want and no fear will stop me” drive she has in her career. She’s scared to zoom her perspective, to “limit” her options. But it is precisely this fear - the fear of defining what she both wants and needs that is “blocking” her. 

Clarity is a super power. You must be courageous enough to say: I know what I want and I know what I absolutely won’t tolerate; and to be equivalently brave enough to acknowledge how you need to grow in order to contribute to the kind of relationship you want. A huge part of gaining this lucidity is through these steps.

Know what is profoundly important to you: Know your nature - do you understand your psychology?

In order to know if a man is right for you, you must first know who it is he is right for. If you were the one being interviewed for a CEO position, would you know how to describe your nature? What is important to you - what aspects of the job you will thrive in, and what aspects of it you just are not suited for?

Yes, I am talking about your values, but go further in your exploration by asking yourself questions: What is important to me in life? How would I like to lead it moving forward? How important is my physical and mental health? Do I love adventure and what kind of adventure? How important is security to me? Is giving back to others critical? What about food, intellectualism, growth, travel and family?.. where do these fall on the importance scale for me? What do I ultimately want out of life? 

If you were to describe what life is about in one word, what would it be? What beliefs do you have that are part of your identity, and which ones could use an upgrade? When you investigate this, you will start to have more insight into your core values. And knowing this is very important when it comes to choosing a man to love. Because his values and his nature must be aligned with yours -  if you’re going to make it for the long term. That is not the same as being identical, (as comforting as it might sound to date YOU, I promise it would dampen passion) it just means you have to be well calibrated for each other.

Know what you need.

There comes a time in our adult life where we must admit that we need certain things in order to feel comfortable and safe in a relationship. Even if it isn't glamorous. Even if we wished we didn't need it. For example, I never thought patience would be way up high on my list of character traits. But it is. I understand without a shadow of a doubt, that I need a man who is patient, specifically in our relationship. I’m not willing to budge on that because I know being with an impatient man - even if he's wonderful, will ultimately bring me a lot of pain. It’s a nonnegotiable for me. I recommend that you take some self - reflective time to figure this out. Get quiet when you do this, so you approach this question from a non judgmental space. Ask yourself what you really needed from your past partners that you didn't get - that if you had received it, you would have felt more safe and fulfilled. Focus on character traits, rather than behavior - such as: Instead of “I need a man who doesn't lie” write, “I need a man who values honesty as high as I do”. or, “I need a grounded man, because I get anxious.” 

Remember, this isn't just about what you want - this is about what you really need in order to be fulfilled emotionally, for the long term. 

Define your absolute non-negotiables.

Life often happens very differently than we expect it to. That goes the same about people. The man you eventually fall in love with may be quite different than what you imagined. He may be from another country, or have children (or not) or look entirely different than what you expected, or he may be an artist if you expected a lawyer - or vice versa. But his character, and equally paramount, what he stands for, is where I’m asking you to put your focus. That is why you must know what you absolutely must have, and what you absolutely will not tolerate - no matter what. Don't make these two lists long. Choose 2- 5 things.

For example:

Your non - negotiables for what you will not accept may be:


heavy drinker

doesn't want kids

Your non - negotiables for what he must embody may be:



values his physical health

These are just examples. Decide what your non- negotiables are. This means that even if you meet a great guy, if he has even just 1 of your non negotiables from your no list, you stop seeing him. NO excuses. NO justifications. It will bring you pain and suffering. That’s why this list can’t just be about preference. It has to be so important to you that you know with certainty that it can’t be any other way, because it will eventually and inevitably cause you pain. Remember, keep it to 2-5 things.

Know what you will tolerate

Don’t let the specificity of these steps fool you - They are NOT meant to block or restrict you - instead, they’re designed to make things easier for you. By elevating your standards, you won’t waste your physical and emotional energy on men who aren’t right for you. By raising your standards, you will be much, much closer to building the healthy, loving, and fulfilling relationship that you want and quite frankly you deserve.

What will contract you is if perfection is your standard. Perfection is the lowest standard anyone can have for themselves and others because it doesn't exist. When we focus on it, we block connection, for intimacy’s commerce relies on our being able to receive love as well as give it.We are all flawed. The question is, what flaws are you willing to see as beautiful in your man?

Know your vision for your relationship.

Gaining clarity can’t just be isolated to the partner you need and want, it has to also center around the relationship you want to build with this person. In other words, connect to the vision you hold for what this bond will mean to you, and to him. Will you build a family? If so, how many children? Where will you live, and where will you travel? How would you like to grow old with this person? Are there experiences you dream about sharing with someone? Will you work together? Do you value an interdependent relationship - meaning you rely on one another, but also value time apart to do separate activities of interest?

Know how you need to grow.

When you gain certainty about the kind of man you need, and the kind of relationship you want to co-create with him, then it’s imperative you’re aware of who you need to be in order to have what it is that you want.

For example, If you value good communication, then it’s important that you objectively evaluate your own communication skills, and work on strengthening them. If you want a positive, and  healthy man to come into your life, you must evaluate your own level of emotional fitness, and if need be, adopt practices to help you elevate your own health and positive outlook on life. If you’re aching for a “real man” - which many define as mature, confident, present, and strong, then you must consider what it means to you to be a “real woman”. It’s crucial that you don’t go down a self deprecating rabbit hole here. You are worthy of love, just as you are. So is “he”. But we all - and I mean -  every single one of us have room for betterment. And just as you need to steer clear of any tendency you have to want to rescue someone, you too must recognize that no one can save you. And as long as you focus on your own progress and persistently commit to your growth no matter what - you won’t need saving. You won’t need love for the sake of love. You will choose it. Choose to give it, and choose to receive it. 

At the end of the day, even if you are crystal clear about what you hold sacred in life, even if you’re certain of what you need, of what you will not tolerate no matter what, and what you must have no matter what, even if every day you devoted yourself to upholding a high standard for your growth and emotional fitness, none of it matters if what he wants is not what you want. In other words, you might meet a man who’ll appear to be beautifully matched with you, but if he doesn't want a relationship - which he makes known through his admission or through another subtler form of message, YOU MUST RUN FAR, FAR AWAY. It doesn't matter if you are the most incredible creature of a woman on Planet Earth - ultimately that won’t matter. Don’t, for the love of everything, EVER try to convince him that he may change his mind, or fool yourself into believing that you can change it. It is an inefficient use of your energy at best, and a drawn out sequence of the push/pull game of stress and rejection at worst.

We have to stop being so afraid. 

And I must note: This is not about having to choose between sexual chemistry vs safety in a relationship. It’s about changing your paradigm of what you find sexy and cool and interesting. It’s maturing ourselves to the point of saying, “no thank you” to someone who doesn't meet our standard DESPITE being attracted to him. Don't be hard on yourself for finding the wrong man hot as hell, just know what you’re dealing with, and decide what to do based on what you KNOW you need and want in your life. That is true accountability, in a really empowering way.

Remember the scarcity mindset? It’s insidious - it can make any respectable, self assured, wonderful woman, such as you, violate her own values just to make the guy she’s in lust with into the Prince she thinks he could be. Our need for romance is that strong. But by violating your values in order to rationalize why you should continue seeing him will eventually hurt. Because, you’ll spend an enormous amount of time worrying about whether he’ll abandon you when the real risk you face is abandoning yourself. And that is a more painful reality to reconcile than his broken promises could ever inflict. 

Does that mean you should barf your needs all over him on date 1? Hell no. My message is not move faster. It’s take your time. Besides, nervously unloading every story in your book is not true vulnerability - its just shows a lack of confidence in both yourself, and in the process of getting to know someone. Vulnerability is being true to you even if - especially if, you may be rejected for it. To be brave enough to stand up for what it is you want. And if he's not interested, capable or ready, to take the risk of saying goodbye even if your vagina says yes.

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