“Why don’t men approach me?”: An epic email exchange on self-esteem and the single woman

I recently had this 5-day email exchange with one of my readers. It brought up a lot of issues which I’ve found are not just common amongst women but pretty much universal. I’m talking about low self-esteem here, ladies. And it seems as if the prettier and more talented a person is, the lower her self-esteem.

To a man observing your magnificence from a distance, this can be baffling. The good news is that after this email exchange, I had some insight into the root of the problem. Read through to the end to get to my commentary. I insert additional commentary [in brackets] where I feel it illustrates a point, or just to crack a joke of dubious taste.

Here’s our exchange below just as it occurred (with small edits for clarity). I have not edited Rosie’s letters since she expressed herself in perfect grammar and without any spelling mistakes. Clearly this is a woman who is highly educated, intelligent, and likely a perfectionist (read: pointlessly hard on herself). If any of this resembles someone you know (ahem!), I encourage you to read on.

On 11/10/13 2:15 PM, Rosie wrote:

Dear Dr. Binazir,

I have a quick question for you.

So I have been trying to go out more often – it’s hard with long hours in lab and a long commute, and I am a bit of a homebody. Nevertheless, I know I’m not meeting anyone sitting on my tush at home, so I signed up for this network that connects people who have graduated from top tier colleges. And I went to a lecture on politics hosted for these people last week.

I went by myself – which is a huge step outside of my comfort zone – because I know groups of girlfriends can intimidate guys. I also followed your 40% rule – curly brown hair down, wearing tight black pencil skirt below the knees and short-sleeve blouse unbuttoned on the low side.

I get there and it was a huge sausage fest, so I’m thinking I’m golden and I position myself near to the men I want to talk to, trying to smile and catch their eye whenever one looks my way (which I’ll admit I do have trouble with since I’m nervous around men, but I’m working on it and fighting through the awkwardness).
And not one approaches me.

I noticed almost all of these men were forming groups of 3-6 guys and chatting among themselves. Not one broke away to talk to me or invited me into their group. I ended up initiating conversation with one guy but that fizzled out once the lecture began and he didn’t find me to continue it afterwards. Needless to say. I was very confused and kinda sad because I thought I had done everything right.

My friend says that since I’m pretty, confident, and whip smart, they’re scared of me and that they were afraid of being made fun of if they broke rank to talk to me. Is this true? I’m literally the least frightening person out there. And was what my friend said the true reason no guy approached me? Thanks, Rosie

On Tue, Nov 12, 2013 at 3:54 PM, <DrAli> wrote:

Rome wasn’t built in a day, Rosie. Keep at it!

Now, if a golden ticket is sitting on a countertop and no one hands it to you, it doesn’t mean the universe hates you. It just means you put constraints on your behavior that didn’t allow you to benefit from the abundance (eg “sausagefest”) that was presented to you. Your experiments don’t do themselves on your own, do they? Well, in this department, you’re also not a potted plant. Do stuff!

So yes, you did some things right (eg dressing up, showing up). But you didn’t do everything right. Most important, you didn’t seize control of your own destiny, and that’s what I sense is missing here. If there’s someone you want to speak to, speak to him. It’s as simple as that. You’ll get better at it the more you practice.

In which city is this all happening, by the way? Best, AB

On 11/12/13 1:20 PM, Rosie wrote:

I’m in DC. Apparently dating sucks here, or so I’ve been told. I have met some guys from the events, I’m just not at all attracted to them like that. [This is the first salvo of negativity. More to come. -AB]

I am very shy around men – always have been – so it is very hard for me to make eye contact and start conversations with them. And then I completely nerd out on them and talk a lot of science and my research because that’s what I do a lot of the time and it’s my passion (plus I work on malarial vaccine development, which I’m sure just reels them in) – or I go on about my favorite off-the-wall TV shows and books and my new rescue cat.

[Notice the expressions like “nerd out” or “off-the-wall TV shows” carry an implicit negative judgment about her perfectly normal tastes and tendencies. The gratuitous takedown of the self begins. -AB]

So I guess I just don’t know what to talk to them about, so I don’t know how to lead into a conversation or be flirty (I’m TERRIBLE at it.). [TERRIBLE!] Or if I do start (badly) flirting [BADLY!] with a guy, it invariably happens that he has a girlfriend and I feel terrible/ awkward/ embarrassed. And I don’t have any other single girls to turn to – almost everyone I know is in a serious relationship or engaged. I don’t want to hear “it will happen soon when you’re not looking” anymore, especially now that it’s the holidays and I know I’ll have to fend off questions from my family. 

I’d much rather be receptive and have them come to me (I am a masculine energy person since I’ve been single for my whole life and have to do everything myself, so I’m trying very hard to accept my feminine energy, which I deny a lot of the time because I connote femininity with being weak). Then I at least know they find me interesting and I don’t feel like they’re just humoring me if I talk to them first. 

[Ever seen a woman give birth? Even better, have you asked your mom how long she was in labor to bring you to the planet? When I was in medicine, I saw women who were in labor for 30 freakin’ hours! Not exactly the stuff that weak is made of. But I digress. -AB]

I guess the reason I feel so down about this right now is because I feel like no guys notice me while all my friends are super happy with fantastic boyfriends. They just talk about wedding Pinterests and themes and I have nothing to contribute and it makes me feel very alone and when you routinely battle low self-esteem, sitting there silently and getting ragged on (albeit lovingly) for becoming a cat lady doesn’t put you in a good headspace. Because if guys did notice me, wouldn’t they want to come up and talk to me? 

[Ladies — guys are noticing you, but it’s not that easy for us to approach you, just so you know. It’s not a trivial thing to put yourself out there and risk your dignity with a total stranger. Again, no need to be hard on yourself.]

On Wed, Nov 13, 2013 at 9:20 PM, <DrAli> wrote:

DC has a surplus of single women over single men, so it’s going to be a little tougher there. Still, no excuse. All you need is one good one :)

Sounds to me like you’re overthinking it. If you want a fuller diagnosis, zap me a photo (especially if in said outfit). Right now I have no idea what these boys are running away from/not approaching.

Also, one of the biggest fallacies of life is thinking someone else is somehow better off than you. Said girlfriends don’t tell you about how the dude leaves his smelly socks around the house, or about the fabulous wedding that ends in rancorous divorce down the road 50% of the time. Count your blessings. AB

[She sends me two photos of her, one solo and one with a friend. Although maybe not five-alarm sriracha hot-sauce hot, by any human standard Rosie is a babe – cute, slim, elegant. I would totally chat her up at a party, especially since I’m a sucker for glasses. Smart girls rule! That said, the friend in the picture is sriracha hot.

Which brings me to one of the only bits that I edited out of The Tao of Dating at the urging of my female friends: If you are hanging out with a friend who is noticeably better-looking than you, most guys won’t even notice you. It’s like you’re the moon, and the sun just came up – poof, you vanish. If you are going out for the purpose of meeting guys, go with someone who’s about as good-looking as you are or less so. As much as I wish it weren’t true, this is the way the world works. And women do it, too, as I can attest to personally. Do not BYOCB to the party (bring your own cock-blocker) – totally counterreproductive. And yeah, that does say counterREproductive.]

On 11/13/13 8:36 PM, Rosie wrote:

I heard that DC’s odds aren’t particularly in my favor (I had to put in a Hunger Games reference, exhibit A of my nerdiness). 

[Approximately 5 squintillion other people also read or watched Hunger Games, so if it’s a sin, it’s a pretty universal one]

I don’t have any pictures of me in that outfit – I usually avoid taking pictures of myself because no matter how good I look in person, I end up looking awful on camera. The pictures I sent you are a bit old (maybe one or two years or so), but I haven’t changed my appearance at all, really. I’m the girl in the glasses. I’m very petite – 5’2″ on a good day, 110-115 pounds or so (I never weigh myself unless I’m at a doctor’s, so I can’t say for sure), huge curly hair, now with red cat-eye glasses. 

Maybe I am overthinking it. I’m a huge analyzer because I’m a scientist and evaluating something from all angles is required for my job. 

[Perhaps it’s a good idea to leave the job behind when you’re going out then, ladies. You don’t wear the lab coat to the party, right?

And I guess you’re right about thinking someone else is better off than you. I do know that it makes me bitter sometimes, but I try to see when I’m getting to that point. Just kinda take a step back and be like, okay, I’m going to acknowledge and accept I feel this way even though it’s not the way I want to feel especially towards my friends, whom I love and am genuinely happy that they’re happy. Maybe it’s because I don’t hear the uglier/less glamorous side of things so all I really hear about is just the roses and poetry and Tiffany’s. And the fact that I literally have nothing – no boy toy, no guy I’m even interested in (and my celeb crushes on Benedict Cumberbatch and Evan Peters don’t count, apparently) – makes it harder to keep smiling.

[This industrial-strength sob story would be funny if I hadn’t heard it at some point from every woman I know. And I do not know who Benedict Bumbersnatch is, but it definitely sounds like the item I’m avoiding on the brunch menu.]

On Thu, Nov 14, 2013 at 2:04 PM, <DrAli> wrote:

You are most definitely overthinking it :) The length of the emails and detailed rumination are pathognomonic for the thinking disease.

[Pathognomonic is one of my favorite words of all time. Worth taking 5sec to google it.]

Instead of ruminating or comparing, start with gratitude for what there is — being young, smart, good-looking and parasite-free is a fine start. Then start having fun with the whole process. Fun has no goal but fun. Play with it. If you keep doing that instead of overthinking, things will have no choice but to shift.

On 11/14/13 12:05 PM, Rosie  wrote:

I am? So does that mean I’m pretty so I’m scary to them? That’s the reason guys don’t approach me? 

[Have you noticed the fishing for validation here? “So you think I’m pretteeee?” C’mon, you know you’ve done it yourself. And have you noticed how I’m not giving any validation? Because outside validation is like crack – one dose just keeps you wanting more. There is no end to that. It’s also an instrument by which women can easily be manipulated. Someone can control you simply by giving or withdrawing approval. To give a momentary bit of approval would be the temporary treatment. But that’s not what we’re looking for. We need to go for a cure. The cure is to stop looking for temporary external solutions and to seek permanent internal solutions instead.]

I don’t know how to play or to have fun with flirting – it’s just anxiety-inducing to me. I do things for a reason. Being efficient is part of my job and my personality. I don’t like putting in effort into something or someone that’s not going to pan out (maybe this is why I failed at online dating, I hated it) AT LEAST for a few dates and good times. So I don’t want to waste my time flirting with a guy only to find out later he has a girlfriend or he is not interested or he only wants to get laid – because when I do put myself out there, this is what happens and I feel embarrassed and sad afterwards. 

So how can I make myself have fun flirting? And how can I make myself more approachable? Any tips? 

On Fri, Nov 15, 2013 at 1:12 PM,  <DrAli> wrote:

Rosie – you need to relinquish your need to be right. Even now you’re arguing with me — and arguing for your own limitations. You sure you want to be right about that? Let it go. I recommend meditation in the morning and two glasses of wine when you go out :) AB

On 11/15/13 10:29 AM, Rosie  wrote:

I just have a hard time actually believing/accepting that I’m pretty. I guess I just assumed since no guys were talking to me, I wasn’t pretty enough to garner their attention. [More negative self-talk and fishing for validation]

But even with the wine, I don’t know if all this will become more fun for me.  

[And now, you get to see the part where I lose my patience]

On Fri, Nov 15, 2013 at 3:27 PM,  <DrAli> wrote:

“And I’ve tried meditation and I can’t keep my mind quiet enough.”

Yeah, and you’ve been to the gym and still haven’t made it to the Olympics yet, you big slacker. You should probably stop exercising for the rest of your life.

Well, I guess you’re right. You’re not pretty enough, you’re not interesting enough, you’re not flirty enough, you’re not fun enough, not mindful enough. So it’s time you found yourself a nice cave somewhere and just retire from civilization since you’re such a total failure! You managed to convince me, so — well done. If I’m your biggest advocate and you’ve exhausted me with your negative self-talk, cannot imagine what you’re like with the other single guys.

Take it easy. And go do something to make other people happy instead of focusing on you and your completely imagined shortcomings.
Signing off,

On 11/15/13 12:47 PM, Rosie  wrote:

Okay, that was harsh, but I needed it. I was mad when I first read your response, but now that I thought about it, you’re right, I just wasn’t ready to accept any of it yet. I have a lot of work to do. I do apologize for subjecting you to all my moping and being a drag.  


On Fri, Nov 15, 2013 at 4:44 PM,  <DrAli> wrote:

This is called provocative therapy or motivational interviewing. You agree with the client’s sob story, then intensify it to the point that she finally snaps out of it and starts to stand up for herself — “Hey wait, I’m not that bad.” Self-directed miracles ensue.
I’m hoping you got that. Part of me thinks you’re actually looking for a cave now.

On Fri, 15 Nov 2013 16:47:48, Rosie  wrote:

No cave shopping going on over here, no worries. I did get it, loud and clear, and it was exactly what I needed. Thank you.  =]


On the last day of this exchange, I went out at noon to City Hall to see thousands of people gathered to make a 5-year old boy with leukemia happy by turning San Francisco into Gotham City. This was inspiring, and it got me thinking that low self-esteem is just another form of narcissism. Get over yourself, be grateful for being alive, and go make someone else’s day.

The Buddhist concept of anatta (or no-self) says that there is no fixed entity you can identify as the self. You’re constantly changing: breath coming in and out; neurons firing; neurotransmitters sloshing around; cells dying and multiplying; tissue being replaced, re-ordered, renewed.

Low self-esteem means focusing all attention on this made-up entity called the self to the exclusion of everything else in the world: the vastness of galaxies; the blue sky that protects you from deadly ultraviolet and cosmic rays; the earth that supports you now and every day, holding you fast and not letting you spin out into space; the fact that 70 trillion cells in your body cooperate every day to keep your heart beating, your lungs breathing and your intestines shimmying even when you’re knocked out cold in bed and have no conscious control over any of it.

You are surrounded by billions of miracles every second of existence. To ignore all of them and to focus on imagined shortcomings of this imagined self is an act of solipsism, narcissism and simple arrogance. Who are you to put down this miracle of creation! It’s like making fun of an oak tree because it’s not a sequoia. Sheez.

The solution is simple, if not necessarily easy: focus on things other than the self. Notice the everyday miracles surrounding  you, and express gratitude for them: “Thank you Mother Earth for holding me up!” Do this dozens of times a day. And then go cheer other people up. Whose answered prayer have you been today? Whose day did you make today? Who did you make feel like a million bucks today?

Service is always an arm’s reach away. Moreover, it’s the only thing that psychologists have found to increase self-esteem. So go forth and volunteer, serve, help out. Read to kidsGive a microloan to someone who can put the money to far better use than you (I just gave 4 of them between the writing of that last sentence and this one — took me 15min). Do it for purely selfish reasons: to make yourself a healthier person.

You ladies often ask me, “Why am I not meeting Mr Right?” And maybe it’s because the universe is doing you a favor. Maybe right now you’re a mess. You have no idea what you want and don’t know how to be kind to yourself, let alone him. If he were to waltz along, you’d screw it up so bad he would speed away and you’d never see him again. And that would be tragic. So relax, take your time, work on yourself, and when you are ready for love, he will show up. Usually within minutes, since he’s either been staring you in the face the whole time or is right around the corner.

And remember not to grasp too hard. What if you were to get that thing you were craving for so long, and then find out it wasn’t what you really wanted after all? T. S. Eliot, one the greatest poets of all time, had something to say about that in Four Quartets:

I said to my soul, be still, and wait without hope
For hope would be hope for the wrong thing; wait without love
For love would be love of the wrong thing; there is yet faith
But the faith and the love and the hope are all in the waiting.
Wait without thought, for you are not ready for thought:
So the darkness shall be the light, and the stillness the dancing.

So relax. Let your mud settle. Take in the good. Meditate. Enjoy life as it is. Do not take yourself down for any reason — your adversaries don’t need any help in that department. Appreciate the miracles. Wait purposefully as you grow. And let the miracles ensue.

18 Comments on ““Why don’t men approach me?”: An epic email exchange on self-esteem and the single woman”

  1. Debbie McCormick

    This was EPIC, Doc. I just learned so many new perspectives it would take too long to name them all. Thank you so much for sharing this exchange, and thanks to Rosie too for helping us all take another look at what we think of as obstacles. Woohoo!

  2. Abi

    Love it!

    I think I could be good friends with this lady. Not to wallow in self-pity with, but for the benefit of having someone totally get you (i.e. i very easily could have written those emails), and to spur you on to getting over yourself and creating the life you really want.

    It’s been said so many times, it’s a cliche,but our beliefs really do create our realities, and if we are responsible for conditions we don’t like, we can equally create the realities we do desire by making the required changes.

  3. Rosie

    Email writer here!

    Abi, I’m always open to making new friends. =]

    I’m glad my exchange with the good Doc is helping people out.

    1. Soodeh

      Thanks Dr. BiNazir :)

      I just wanted to tell Rosie that I’ve been feeling the exact same way, and it is because we are used to focus on undesired points of everything. It’ll take some time and everyday practice to get the feeling of appreciation and beauty in almost everything in this world!

      I used to feel very ugly, but I’ve also seen that every time I was happy and felt pretty and thankful for whatever it is, I’ve attracted guys even just because they liked my face!!

      so, good luck dear Rosie, I know we can!! :)

  4. Soodeh

    Thanks dear Dr. Ali.

    I remember the time that I used to feel just like Rosie, and I still do sometimes! but there’s an awesome fact here, and it’s that if you feel pretty and happy, and enjoy your life, people will notice it. I have seen lots of “not that pretty” girls who are happy with what they are, and they get a lot more attention.

    I exactly know how Rosie feels, because I used to feel very ugly too, but I have also noticed that every time I felt “pretty and thankful for whatever it is” guys showed up just because they liked my face!!

    So, dear Rosie, it’s hard to admit all this beauty in the world just because we focus too much on undesired points. But have faith, cause it will be awesome and wait cause it will take some time honey! :)

  5. Seema

    Absolutely amazing Dr. B!! Among the billions of miracles that makes me who I am and for what I am grateful for, one more is that I came across this article. Thanks and God bless! :)

  6. Lisa

    Thanks for posting! I am in a place very similar to Rosie’s. I’ve read the “Tao of Dating” through a couple times – but self-esteem issues run pretty deep. It’s hard to realize that I’ve probably scared away men with this type of behavior.However, I can say that I have experienced my “light” shining and what that can do (2 different men approached me in the same week)! The trick is to keep the light on – not snuff it out. Please keep posting – this helps so much!

  7. Jan

    I’ve been told (by a guy) I’m so beautiful the guys were afraid to talk to me, but I always supposed hardly anyone approached me (in person; people like me online) was because I was smart/educated/nerdy and this intimidates them, and because I did not dress fashionably, and appear younger than my age, and am not a good conversationalist (particularly in voice).

    I feel not beautiful, but at the same time I have noticed distant attention from guys.

    This post was very helpful to read.

    Thanks to Rosie and Dr. Binazir.

  8. Danyel

    To Dr. Ali, Rosie and all of the ladies who have commented,

    I came upon this article looking for answers for what was wrong with me and why guys don’t approach me. I am glad, and sad, to see that I have been creating problems in my head. Over thinking the smallest situations and causing myself much unnecessary depressed moments. Its also gives me hope that there are other women out there that will be working on focusing on the positive at the same time as myself.

    And thanks Dr. Ali for pointing out that it doesn’t make much sense to get what you really want when you are a complete ball of mess. I’ve been crazy about a guy friend for a decent amount of time and get super frustrated because there are definitely times when I feel it’s mutual, but then there are times when he seems very off-put. In hindsight, these are times when I was a complete negative monger and probably was a jerk to him. Maybe with this new insight, I can get myself together and things will come around.

  9. Peachie

    WOW Rosie, I just read all about myself in black and white. You have no idea how much your life story helped me get out of my own way. We woman are a very complex creature that sometimes have to be threaded around lightly. Well NO MORE. I say. I want to share my life with someone who is worthy of me, just as much as I am worthy to him.

    thank you so very much

    God loves you and so do I

  10. Valentin

    Women look down on all men that require some reciprocal encouragement and pleasantness in return: not to mention not having our time wasted as “friends” and just be straight with us. And that’s alright, but whining about the consequences of this attitude that men filter out entitled women on a very unfair dating market is just ridiculous.

    You’ve told men over and over how amazingly smooth and suave they have to be to even get a little attention from you, let alone be attracted. You’ve told men that if they don’t live up to your expectations they’re jerks for expecting anything just because they’re trying/being nice.

    Your message was clear and well received, noone is good enough for you unless they’re that alpha cad. Well, OK the men said and went bye bye. What are you trying to say? That you still want all that attention for your pleasure from men who you clearly state aren’t attracted too for not being amazing alphas that pass all your shit-tests?

    Well then, there’s your simple answer for this question. They’re not approaching because you’ve clearly outlined they have no chance to begin with. You either see them as asexual non-entities or as inexperienced suckers that will give you all the free emotional support of a boyfriend with no sexual relationship. Message received and accepted: don’t complain you got what you wanted.

  11. dave

    Valentin – You really have to watch what you say.ANY comment that is any way contrary to the woman’s opinion gets you a certain label, and you certainly cannot EVER suggest that men should ,gasp, share any kind of hesitation or reluctance to approach the opposite sex since you are then called “whiny” and sick. Just recognize the double standard that women should never be “embarassed or sad” like men need to be for approaching.

  12. Cristina

    Wow! What a reality check reading this article was! It’s like reading my own life (specially the crushing on Benedict Cumberbatch part…thought I was alone on that one, lol). This has been very eye opening for me. I’ve been, for as long as I can remember, a single gal. Friends have told me guys are just terrified of approaching me, since I always carry myself around like I need no one else’s companionship (I’ve been raised by a tough-a** mother who always encouraged me to be independent and take no bull from men…so yeah). So, I guess that just puts them off. Well, this will no longer happen. This article has given me the green light to move onward with a brand new attitude towards life…and men too. Thanks Doc!

  13. Fillian

    I have to say thank you! I am going through the same situation and this just put a plethora of things into perspective! I am so glad I came across this post!

  14. yosmeiry

    not only did i realize what i’ve been dong wrong but forget the things that need to be appreciated out there and being humble and communicating helps in many ways…ill take time though thinking i want to be with somebody is such a selfish act of my own wanting someone to love me ….maybe its just better the way i am and learning to lift up this self esteem and loving myself is all that matters and need because thats how ill learn to live by

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