Screen Shot 2016-03-14 at 5.18.16 PMThere’s no shame in being lonely.

That’s what friendship expert (and friend!) Shasta Nelson, founder of GirlfriendCircles, said to a group of women at the launch of her second book, Frientimacy: How to Deepen Friendships for Lifelong Health and Happiness.

And yet, the word “lonely” itself is scary. Even those who love and treasure their solitude (um, me) don’t like the word lonely, and certainly won’t cop to it. Why? Because of the horrible picture it paints. No matter who or where you are.

If you’re married and lonely, well, something must be ‘wrong’ with the marriage or with your partner, and you’re not having your needs met;

If you’re dating and lonely? You haven’t met the right person or are wasting time with someone(s) who can’t fulfill you.

If you’re single and lonely, well, it’s your fault. You worked too hard and didn’t put enough stock in finding your perfect match. (If you own a cat? Forget it.)

There’s the rub: If I admit I’m lonely, then I have to admit that something’s wrong with my life, or me. And that I may in fact be doomed to a life of it. And so we do everything we can to point away from loneliness: “I can’t possibly be lonely! Look! I’m up to my ears in work! I have been out every night! I have friends up the wazoo!”

Most of us don’t say we’re lonely because of what it would imply: That we’ve done something wrong or that our lives and its brimming obligations and people aren’t cutting it. That it’s all a sham. And that’s scarier, perhaps, than loneliness itself.

And yet, it’s not true.

Loneliness is a symptom, not a disease

Shasta said this, and it is brilliant: Do you have a problem admitting when you’re hungry?

Of course not! If I’m hungry, I say, Gee, time for food. Let’s see what I have here in the fridge. Nothing? Out I go. (This is a very common occurrence.)

The urge to connect with people, to be heard and seen and known, is as normal and regular as basic hunger.

If you cannot admit that you’re hungry, you’re going to have a very big problem, very soon. And plenty of people DO struggle with hunger and what it means. And they suffer dearly because of it. They need medical help. But most of us answer the call and put food in our gullets.

However. If we cannot admit to bouts of loneliness, be they a blue moment or a soul-shaking cry, we have a real problem. And Shasta says that it’s this inability to look our loneliness in the eye and accept it for what it is, a basic human hunger, we cannot and will not be able to address it.

And therein lies the problem.

I’ll start.

Yes, I have a full, busy life full of friends I can call, a close relationship with family. I go on dates and get invited to events and have my share of professional and personal attention.

And yet, sometimes I feel lonely.

While I put a premium on alone time, sometimes I feel that tug, that wanting to be known, seen, touched on the shoulder. Someone who says, “Come and meet me. I need to see you.”

We all need this, and as with real hunger, there is no end to it. Not in this life. And that’s ok! You’re not doomed to a life of loneliness. Anymore than you’re doomed to a life of hunger just because you missed lunch.

(I’ll add that women are terrified of coming off as “needy,” and are told it’s a bad thing to need, so many of us put feelings and need on lock-down, which has just as damaging effect. “Neediness” is a drowning person who will take you down with them, and no it isn’t healthy. But need is different. Dismiss need and you will also ward off connection.)

When loneliness shows up, as it has, does, and will, take note. Don’t create a narrative around it (unless you find it useful for your novel or opera, sure.) Instead, say simply, Huh. Guess it’s time to feed my hungry little soul.

Then: You reach out, give attention, show some love. Call and text and email folks. Invite someone out. Show up to something. Raise a flag. Let people know you’re there and interested in what’s going on with them.

You don’t need to post on FB that you’re lonely. Do you do that when you’re hungry? No. You simply go find something that nourishes you. And the beauty of the transaction is that when you give what you need most, you have plenty to go around.

Are your friendships as fulfilling as they could be? Take Shasta's quiz to find out!

Are your friendships as fulfilling as they could be? Click here to take Shasta’s quiz and find out!


Take Shasta’s quiz to find out if your friendships could use a little more love.

Screen Shot 2015-06-22 at 11.10.22 PM“My boyfriend never had any hesitations about being together: He wanted to be with me, live with me, marry me. For years.

One day, I come home to find that all his stuff is gone. He says he’s “confused” and isn’t sure if he loves me anymore. He says he met someone else. He takes down our Facebook pics, and puts her up instead. Then, he starts blowing up my phone, wants to hang out, so I say ok, and then he’s distant again. He tells me I’m his safety net. I know I’m a better fit for him—better looking, his age, with a good job and my own apartment. What gives?”


Oh boy.

This is the rock we beat ourselves against, over and over: We think that we know what’s “better” for the person we love and want, and decide our life should be dedicated to proving this fact, or at the very least, suffer endless indignation over it. I have done this many times over myself. Fruitlessly.

Let’s get this out of the way right now: It’s not about looks. Or income. Or your apartment. And what he thought or felt back then has little to do with what he does now, because we live in the present, which has been known to change. You say he never questioned his commitment to you…until he did (though did you ever think your hesitation may have played a role?). We don’t know that what he felt then was real and now is a mistake. He might have just bulldozed his way in because he wanted to. And is backing out now because he feels like it.

It’s not fair. It’s not fun. It may not even be logical. But none of that matters.

Because here’s the thing: relationships are not a logical puzzle that you solve by being the answer or getting it “right.” And the idea that being the rational choice assumes that relationships are rational, intellectual decisions. Hardly.

They are emotional, and based on how we feel, or think we feel, right now, rather than what looks good on paper (and those who go that route aren’t any happier). You may choose to ignore or repress them. Or you may choose to follow them, much to the dismay of everyone else involved.

It can be frustrating, maddening even, when someone you love willingly chooses someone you think is “all wrong” for him (or her, bear with me with pronouns here). Ask any first wife. How many beautiful, smart, capable women have watched partners cheat or leave altogether with women who are younger, dumber, broke, 20 pounds heavier, a smoker.

Good looks, a sense of humor, a string of accomplishments, and a killer bank account are not a vaccine for loss (see: Anyone with even one of those things). And the sooner you realize that, the better.

Men leave women who love them for women who don’t, or women who treat them badly, or women who just suck. And vice versa. Even when it’s deemed wrong or unethical. (Do I have to take you back to Hugh Grant and Divine Brown?)

And that’s why to assume that it’s you, or something you could have done differently, is not the answer, and it’s certainly not helpful—except that, more often than not, it helps YOU because it allows you to decide he’s stupid, wrong, making a mistake. He may be! But he’s making it anyway.

Stop wondering why he so clearly isn’t choosing the “right” fit for him. Because you’re missing the most important part of this picture: Since when was this all about how you fit his life? Don’t you also want someone who fits into yours? Because he doesn’t fit. He walked away.

I can’t read his mind and I don’t know you, Alice. But I know that if you have to build a case for why he should be with you, no case will ever be enough.

I once had a boyfriend who was 100% not a fit for me. At the time, he was earning his MBA from Harvard, and fancied himself a bit of a brainiac. And he was smart. The day I went over to end it, because the whole thing was making me nutty and not in a good way, he talked me out of it. He said, and I quote, I didn’t have a good enough “argument” for breaking up with him.

I was dumbfounded. I didn’t have an argument. I just started to cry. He attempted to intellectually bully his way out of a breakup! I’d never seen anything like it, before or since. It ended not long after.

So do yourself a favor and stop trying to rationalize why he should choose you and acting as if the court should rule in your favor because he has mistreated you. Besides, what do you win? Him? You don’t want him, trust me.

At some point, you have to take ownership of your role here. If someone can’t make you feel inferior without your consent, then no one can make you their safety blanket unless you continue to act like one.

*Alice is not her real name. I paraphrased her very long letter, and disguised the details a bit because she really does not want him to know. Obviously.

Having some dating issues or feeling stuck? I hear you. Truly I do. Use this link to get 25% off my online course, Stop Hating, Start Dating – I will change the way you think about and approach this whole thing. 

subway - mediumLove can happen pretty much anywhere. And your local public transportation system is teeming with love-hungry folks. The train (or subway, or bus, whatever) is a cocktail that’s being shaken around the clock: You never know whom you’ll end up next to or when.

And since you may find yourself on the subway at one point or another, there’s no reason you can’t make a connection there. You don’t need a bartender in range to connect with another single person. So, here are my tips for meeting someone on line—the MTA line, that is.

1. Get within 5 feet of that person. Obviously, you’re not going to yell across a car, especially a crowded one. Work your way into that person’s vicinity, but do it nonchalantly, as opposed to making a beeline, which can come off as aggressive.

2. Make eye contact. Now, granted if this person is staring at their phone, staring them down won’t work and will come off creepy if and when he or she happens to look up. If you DO make eye contact, don’t hold it like a crazy person, but smile and hold their gaze for an extra beat, then look away (this is, of course, Flirting 101). SMILE IS KEY—it registers a connection right away. It says, “I have noticed you.”

3. Initiate a conversation. This is key if there really is no way to make eye contact because s/he’s staring at his phone. And don’t delay. Time on a train is limited, and he who hesitates is lost. The longer you wait, the more likely you are to lose your nerve. Resist the urge to script your conversation preliminarily, because that’ll create more mental obstacles. Just start it, and let it go where it goes.

Now, the initiation has to feel natural to you. And so I offer you a few options, and what feels most natural to you will depend on your personality type. The idea that you “can’t” start a convo b/c: you’re introverted, shy, a girl—all that is garbage. You don’t need to be some alpha dude to start a harmless convo.

a) The question. This is the most harmless way to break through the stranger-veneer is to simply ask something. You don’t have to pretend to be a tourist (bad idea to lie) to ask a simple question (I do it all the time, for reals). “Hey, do you know if this goes to Wall Street” or “Do you live in this area? Would you happen to know if…” fill in the blank.

This serves two purposes: one, it breaks thru the silence and establishes contact, but it also puts the other person in the position of confidence and power because you are asking for their help. Trust me, this is key. I’ve had people ask me as I’m reading my Kindle, “So, what do you think of that Kindle?” and I am happy to talk about it.

b) The compliment. Flattery will get you everywhere, or at least, most places. It’s true. The hottest girl and even the most styling dude can’t get enough of them, nor can the rest of us. But there’s a right and wrong way, and there is a gender breakdown.


Cute girls will be on guard, because they know that compliments, while nice, can raise a flag and we wonder “What does he want?” So avoid anything that makes them feel put on the spot in a weird way, like “You have such beautiful eyes” or the like. Don’t make it sound like a line. Give a genuine compliment and give it with no strings attached. I’ve heard women say they don’t like when someone compliments a THING they have/own (“Who makes those cool shoes”) because then it’s more about the item than, well us. But I still think it’s ok, as long as it’s a genuine compliment, and I’m in there somewhere (“Cool shoes. They look great on you.”)


Men don’t get complimented all that much (maybe ever, especially by strangers), and they want them as much as anyone. So you kinda can’t go wrong here. A genuine, friendly compliment on just about anything will open a guy right up. In this case, I DO think complimenting a guy on what he is wearing/has is key because it not only says you noticed, but confirms his good taste. Ladies, you have it easy.

I will underscore this next point: DO NOT give a weirdo pickup line. I shouldn’t even have to say that. For this to work, it has to sound like genuine, spontaneous conversation.

c) The shared moment. Crazy stuff happens on the train. When it does, I consider it a gift from the subway gods. Use it. A mariachi band comes on at 8:30am in full regalia. A crazy person starts singing opera on the L. A couple starts yelling at each other. Who knows. If it happens, it’s a great opportunity to connect with this person in a way that is memorable, because it’s something you experienced together.

This is where humor really comes into play, and if you happen to be funny, witty, or observant in any way, this is the time to strike. You can make eye contact, roll your eyes, and say something like, “Man, I can’t stand mariachi in the morning. I prefer it on an evening train, during happy hour, don’t you?” You don’t have to be Louis CK to make someone laugh to get a response. It’s often a great tension breaker, and people get nervous on the train.

4. Move the conversation along. You established contact. Great! Now, move past whatever sparked the convo (the Kindle, the great shoes, etc) to real conversation. Unless all you really wanted was a consumer review of e-readers, and I doubt that. Nor is it really a shoe conversation. You want to see if you could connect with this person in a real way. Here’s where you can say something like, “You look familiar. I’m sure I’ve seen you on this train before. Do you work downtown? Yeah? What do you do?” And you’re off to the races.

5. Get a name, a number, website, a Twitter handle, anything. Remember, the goal here is not to have restaurant reservations or know her life story before you reach 72nd street, but to establish some kind of connection so that you can be in touch once you part ways. That and that alone is the goal of an en route meet-cute.

Ladies, you can do this as well as a guy can. You can say lots of things besides, “Can I get your number,” which for some reason, I’ve never liked. It sounds like you’re asking for a handout, unearned. The key is to make sure that person knows you’re interested in him or her. You must take the risk here and let someone know you’re interested in THEM, and while I know that’s the most terrifying part, all of this is worth nothing if you don’t do it.

Some options:

“I’d love to see you more than just by accident. Want to get coffee sometime?” or “Well, look, you seem really cool and I’d love to see you again, but on purpose. Can we stay in touch?” See? Harmless. Men, I’d offer your card if you have one but also get her info (whichever way she prefers—email, text, Twitter, whatever). You can take a moment to key each other’s info into your phones, but the problem is if you forget that person’s name, good luck finding it. Again, time is of the essence.

Ladies: I see no harm at all in offering a card—a biz card is fine, but it’s not a bad idea to have basic contact or ‘calling’ cards as they used to be called that has the info you want to share on them. Bottom line here, if you feel weird asking a guy for his number, etc, I like offering a card and saying, “Email me if you’d like to get together sometime.” I’ve done it many times to strangers I’ve met—some called, others didn’t. No harm, no foul. One did. That was all that mattered.

(Check out more advice on subway meet-cutes in this story on dnainfo.)

Swipe left.

Swipe left.

I’ve recently re-entered the online dating pool, and surprise surprise, it’s just as much a hot mess as it was last time I was here. The bare torsos, the cringeworthy cliches, the fevered search for the next quick hookup.

But something has changed. The process has gone from a desktop portal of long-winded applications and essay contests to something far more visual and visceral. In other words, something more akin to how humans date. Less of a slog, too, and a whole lot more fun. Outside of the meet-someone-at-your-friend’s-bbq option, online dating has become more human than you think. And if you’re not doing it, as far as I’m concerned, you’re not really in the game.

We all have Tindr to thank (and Grindr before that) for disrupting the old college app-slash-memoir model, and making online dating feel faster, sexier, and more fun. Yes it’s a game. But you already knew that. It’s a handheld adventure, characterized by quick glances and physical gestures (the most important being the almighty swipe).

Now everyone’s doing it—you’ll find swipe functionality on OkCupid, Hinge, even Match, the old granddaddy of online dating. And don’t forget Cheek’d, which has also gotten some attention lately. After Lori Cheek, its founder, got chewed up on Shark Tank, she emerged with a new heat-seeking missile app which leverages the power of the virtual in the real world, letting you find other single people whom you may be missing on your daily commute or anywhere else. (Check out my interview with Lori on my show, Solopreneur.)

Rather listen than read? Done.

Guess which one's me!

Guess which one’s me!

It’s Like a Little Vegas You Hold In Your Hand

Your phone is now the portal to your love life, part mission control and part slot machine, complete with colors, movement,and flashing lights. But you have little to lose, and it’s hard not to get hooked. And you don’t even have to be dating to have fun doing it. I know more than a few happily married people who serve as Tindr proxies, swiping on behalf of their single friends. They want to help their friends find someone, sure, but they also want to play.

Some daters decry this shift in online dating gamification, saying that this doesn’t give them a chance to make their case, that this makes dating all about looks and nothing else. I have to remind them that we are human animals first, we’ve always looked and responded from a gut level, for millions of years before we wondered how people looked on paper. Sure, maybe you change your mind or someone wears you down. It happens. But I trust the gut check, always have. By the way, when in the history of human coupling has anyone met via a complicated admission process, complete with test scores and extra curriculars? I’ll tell you when: Arranged marriages, and you wouldn’t have been the one screening applications.



Partnering isn’t an executive function, not at first anyway. (See: Anytime someone looked great on paper but not in person. See also, anyone who swears they fell in love at first sight.) It’s not that people have gotten more superficial in dating–I don’t even know how that’s possible. So if you’re telling yourself this story, stop.

Don’t Be an Ass Swipe

What that means is that yes, pictures do matter, and I don’t mean you have to be a beauty queen or prom king, but you must show what you look like now, and not when you’re wearing a complete head-to-toe diver suit or dressed up as Lady Gaga. Getting a butt-first shot of you belaying down a mountain is not ideal, nor is a profile picture of you and several friends–because while you know which one you are, we don’t. Because when we finally do the task of flipping through your photos to find the common denominator, you don’t want us to be disappointed that you aren’t your hot cousin.

If you’re a dude, we don’t need to see pictures of you with a beautiful lady–sure, it may be your sister, but it could also be your ex. Maybe subconsciously you want to show your cred (look at what I got, or at least had). But while that works at parties, for some reason, it doesn’t play in pictures.

Don't you want to date me?  I'm available, like all these chairs.

Don’t you want to date me? I’m available, like all these chairs.

An anthropologist could have a field day studying men’s online dating pictures. I already do. But it goes without saying–if you want more right-swipes, avoid at all costs the bare torso, the blurred bathroom selfie, or you holding any kind of weapon. Skip the the landscape postcards, the still life. Keep that on your Instagram feed. And realize that what you think looks cool (you in your shades looking somewhere in the distance, often comes off as cold, intimidating, or a straight-up turn-off. Instead, try the one thing that so few guys do: Smile. Right into the camera. A real smile: eyes crinkled, teeth showing, you at your warmest and most real. That’s enough to give a thumb pause, and make us think you’re someone we’d like to meet.

I prob won’t text you back b/c I’m so cool and busy making deals by the water!

This comes from a quirky tumblr called "My Daguerrotype Boyfriend" Click to view all of its weirdness.

This comes from a quirky tumblr called “My Daguerrotype Boyfriend” Click to view all of its weirdness.

I’m going to confess to you, right here and now, that I have done feminism a grave disservice.

And I’m a repeat offender.

I have used the “I have a boyfriend” excuse to duck, dodge, or deflect unwanted attention. On many occasions.

I said it when I was 100% single. And every time I’ve said those words to someone I know I just really wasn’t interested in, I’ve felt a hiccup of self-loathing, and had the unsettling sense that I was trying to hide behind my high school boyfriend’s Varsity jacket.

And that’s because telling a guy you aren’t interested in him because you’re “taken,” whether you really are or not, undermines your respect and self worth. Using an excuse (“I can’t”) in place of my opinion (“Not interested”) is triggered by a lousy premise: That “he” is the only thing keeping me from flying into the arms of any man who will take me. Every time you and I rely on this cultural crutch, we vote against ourselves, again and again.

The thing I hate most about the boyfriend line is that it works.

But at what price?

When you lie about having a partner to turn someone down, you’re basically saying that any man’s claim on you is more powerful than your own, even if the man does not exist.

(And no, it’s not quite the same as saying “I have a work thing” when you don’t want to go to another thing. White lies have their place and don’t get me started on that.)

Listen instead!

By the way, it’s not that your boyfriend isn’t enough of a reason not to run off with someone else. Of course, if he exists and your commitment is real, you will show that bond respect—but that’s your business and your choice. Let’s not pretend that people haven’t fallen in love with other people regardless of their relationship status.

In fact, the only time it is ok to use your boyfriend as an excuse is when you literally WOULD love to get to know said guy better, but have to pass because you are in a committed thing. But even then it’s not blaming the boyfriend, but owning up to your decision to opt for your current relationship over this new potential. The difference is between honoring your commitment and apologizing for not being available. And there is a difference.

Look, I get it. You, like me, have been taught to adhere to that genderized Hippocratic Oath from a very young age: “First, do no harm.” And the second unwritten rule, which is “Always be liked.” That one’s got a bigger grip on you than you realize. Because even if you don’t want to date this guy, you don’t want him not to like you (admit it).

It’s worth adding that our collective memory is strong, and resisting men hasn’t really worked out so great for us, pretty much throughout all of human history. And there’s still plenty of reason to fear. (Do we need to revisit the horrendous stabbing of a Connecticut student when she turned down a prom invitation?)

But if you want to be taken seriously and want your choices to be respected, you need to start owning them, instead of excusing them. A rebuffed man may very well accuse you of being: a bitch, a lesbian, a bitter old spinster. And sometimes, in the case of a drunk old crazy guy, if a lie would save your life, ok fine. I’m just asking you to think twice before you blame (or credit) other people, man or woman, for your own choices. Because if you don’t own them, who will?

Ask it and you're not bringing sexy back.

Ask it and you’re not bringing sexy back.

Please, for the love of all things holy, stop asking the people you meet online if they’ve “had any luck” on the site. Stop, stop, stop.

I realize that you think it’s just in the spirit of fair gamesmanship (“hey we’re all on this together,” and “I’m such a good sport about this”) but you might as well sip your pinot grigio and ask, “So, who else are you currently fucking? How’s that going?”

I am convinced it starts innocently enough: a little conversational wind-up, some basic throat-clearing before you plow on to more interesting topics. You also might be genuinely curious. But when you ask this question, you break the romantic spell. You call uncomfortable attention to the obvious: “I know I’m not the only one you’ve met on there.” And it just doesn’t need to be said.

There just is no right answer:

“Oh it’s going great. I’ve had so many dates. Who knew that getting laid could be this easy?”

“It’s terrible. No one will write me back.”

“It’s hard because most guys are such assholes.”

You either sound like you don’t really need to be on this date, or that you need it too much, or you come off sounding like a beleaguered, judgy prick. It’s a lose-lose. It also puts you in a tempting position to denigrate those who’ve come before this date, and it’s an uncomfortable foreshadow (“What will she say about me tomorrow?”) Save the dishing and piling on and other fun nastiness for your friends.

Case in point: A guy I met on OKCupid a few years ago asked me what I thought of the site. When I gave a vague response, he jumped in to tell me how horrible it was: “The women in New York City are such gold diggers, always making you pay for shit.”

SHSD image

Need a little extra help in the dating dept? Check out my online workshop–risk free.

We were at a tea shop at the time, and when the check came I whipped out my wallet so fast—I felt pressured to prove that I Wasn’t Like Other Girls, and certainly not attempting to work him over for an earl grey. But he was all, “Nah, don’t worry about it. I got this.” The whole thing left a bad taste in my mouth. He only had bad things to say about the women he’d met. And yet the only thing they had in common, as far as I knew, was him. He texted the next day; I never wrote back.

Asking how your date is faring romantically is the fastest way to suck the sexy tension out of the room. If you wonder why your dates feel more like interviews, it’s because you’re treating them like a job fair (“Got any good prospects?”).

I’m all for honesty, but not to the extent that you let fly your wrath or judgment or even mild disappointment—directed at an entire gender, population, or unfortunate dates. (See also: Talking about your ex on a date. Another no-no). You risk painting yourself the bitch, the dick, or the victim. And none of that looks good on you.

Plus, in all honesty? It’s really none of your business. I say that in the best way possible. It literally isn’t—so why burden yourself with more info than you need at the moment? Just because you’re sharing tapas with someone doesn’t give you access to their entire personal backstory, nor do they have access to yours. It’s a date; it’s a time to be choosy, and to ask questions you really want the answers to.



If you can believe in this, you can believe in an OS you can love.

If you can believe in this, you can believe in an OS you can love.

I love my Mac. Sometimes I take it to bed with me, it’s true. Though, things between Siri and me are somewhat strained (she still can’t remember my mother’s name? Really?). We’re all in the thrilling, flirty phase of modern tech. We’re intrigued, turned on, and yet there’s still a lot of awkward. We’re still getting to know each other.

I’m holding out hope that Ray Kurzweil, considered the world’s leading expert on artificial intelligence, was right when he predicted that by 2029, computers will be smarter than us. And what’s more—able to respond in a way that’s indistinguishable from a human, even cracking wise and flirting. I’m ready for it.

I don’t want to just “master my mac”; I want the tech I rely on to know me, too. And Spike Jonze’s film Her made me realize how badly I do.

Before you saw Her, you might have assumed a movie about a man who falls in love with his operating system would amount to little more than a futuristic doomsday tale, a sign of our collective downward spiral in which we mistake things for people and dependency for relationship.

But you’d be wrong.

Spike Jonze’s brilliant depiction of a man searching for connection in a not-so-farflung future was as optimistic as it was heartrending. His supremely intelligent OS, “Samantha,” is not some static bot that does what you tell her to; she has thoughts, opinions, a sense of humor. And, what’s more, she evolves—light years faster than a human (which ultimately proves the breaking point). Unlike sci-fi type films in which humans come up against the limits of the machine, this one does the opposite, revealing its almost divine nature, and our own finite nature as we plod along beside it.

We Expect Too Much from Humans

I had the pleasure and honor of interviewing Esther Perel for a feature in Experience Life magazine (“Your Brain In Love”). (If you haven’t read her book Mating in Captivity, stop and send it to your Kindle immediately.)

Perel, who has become the go-to expert on sexuality and relationships, told me in no uncertain terms that we have come to demand far too much from our relationships—more than ever in human history:  We want the other person to be our best friend, confidante, long-term domestic partner, perfect match, true love, and at the same time find us wildly attractive and never consider another partner for as long as we both shall live (which is getting to be quite long).

(Watch Esther’s TED talk on desire in long-term love).

Is it any wonder so many relationships and marriages are doomed? Something’s GOT to give. And while Perel’s advice—to allow desire to breathe with a degree of space and uncertainty—is vital, it wouldn’t be a bad idea to supplement our hungry and ceaseless demand for support, attention, and love. To have a kind of better boyfriend.

Enter, the OS. Just as you depend on technology to organize, execute, and contain your whole life, from your creative work to your bank statements, you and I will both benefit from having this intuitive consciousness in our lives.

How an OS could make a better boyfriend (or make your boyfriend better)

1. Being heard.

All the time. Imagine having someone in your ear at any moment, who can help you do things that your partner isn’t always interested in or able to help you do. And while your partner loves you, you know, sometimes he needs a break. We all do. The need to be heard lies at the root of all of our kvetching and resentment, our aching needs and horrible acts.

But beyond that, imagine that you could allow your partner to be, rather than constantly weighing his or her worth based on how much they listen, do, or participate in all the things you want to do. And not worry that someone isn’t your “perfect partner” because they don’t like watching Real Housewives or taking yoga. And the reverse would also be true: YOU would not need to be everything to your partner, either. Wouldn’t that be a fucking relief. You could love each other for who you are, and not as you wish you were.

2. Intimacy instead of mutual neediness.

The assumption is that when you’re in a relationship, you should be the go-source for all connection. If you’re like most people, you think that the key to being secure in a relationship is locking them in. There. Now I’m safe. That may be what you think we need, but is it? Does it serve us and our relationships, or just our own selfish needs?

Perel would likely nod again at our outsized expectations of each other. You’d feel more intimate and desirous if you weren’t so busy trying to staple someone around the edges and keep them there. To have and maintain a relationship that supports you for many years, if not all of your life (though I think even that is somewhat unreasonable), you and I both need to redefine what we expect from them.  And the answer can’t be “everything.”

3. An evolved, even divine, kind of love.

When it comes to light that Jones’s protagonist Theodore Twombly isn’t the only person Samantha (the OS) is connected to, he goes cold, fearing that this means she’s “cheating” on him or can’t possibly have real feelings for him. She explains that she’s different from him; that the more she loves, the more she’s capable of loving.

Now, that’s an evolved idea—and one we humans would have a hard time doing, given our own limits of space and time (do you have time for 15,000 other boyfriends?). But I like the idea. If you believe in God, then you already believe that He can love other people and you and that his love isn’t fractured or compromised because, say, there’s all of a sudden more needy people than you on the line.

If you don’t believe in God, you probably still believe in the sun. And you know it doesn’t take any more effort on its part to shine as strongly in Arizona as it does in Florida. What if we could try to see our own love that way—as sustainable, instead of limited?

We possibly could, if we were willing to wrestle with our reptilian brains and fumbling animal ways, our starving egos. Maybe we could get there. And I don’t think you have to ascribe to any religion whatsoever to see that this as ideal, as the highest level and fullest expression of love.

That would make an intuitive consciousness like Samantha the closest thing to God we could directly experience or create. That would be divine love. A God you keep in your pocket. Sign me up.

If you love Jesus, you probably hate this idea

I’m sure just the mere thought is causing God-fearing folks to choke on their chicken casseroles. “That’s worship of false idols! That’s loving tech more than people!” or, my favorite: “That would prevent us from connecting with other people! It would be isolating and horrible!”

Would it? So let me ask you, is a church-going person with a strong bond with his or her personal God, less likely to connect with someone else? Are people who believe in a source of eternal and unabating love less likely to go out, meet, and love others? Nope.

Sure, there are religious crazies. But there are crazies everywhere. For every person who gloms on to his iPhone and never goes outside again, there will be hundreds of thousands—millions— who would walk a little taller in the world, feel more loved, more confident, less needy. And a person who feels her needs are being met is in a position to do more good in the world than bad.

It’s closer than you think.

It’s gonna happen

If Siri can help me find my way to a sushi bar on the East side, who’s to say at some point she won’t be able to help find my life purpose, too? You never know. And if you scoff at the idea, you’re not smarter than a machine. In fact, you’ve just proven yourself squarely human, resigned to your own ideas and limits of how and what could happen.

What you should worry about

During a critical moment in the film, Samantha struggles to explain to Twombly that she is having feelings and thoughts she never had before, that she’s evolving so fast in ways she can’t communicate and he can’t understand. The real threat isn’t that the machines will rise and turn us into housepets or kill us altogether. It’s that they’ll see us for what we are and what can’t be; that they’ll break our hearts and move on.

Screen Shot 2015-02-04 at 5.41.10 PM

Don’t hate on Valentine’s Day.

It’s easy to pile on poor Valentine’s Day. And if it makes you feel any better, a rather small slice of the population is really psyched about it.

If you’re single, chances are you roll your eyes, flip couples the bird.

If you’re in a long-term relationship, maybe very long, this holiday makes you nostalgic for the days when romance was new, before either of you peed with the door open, and when you had time or interest in having sex more than once a month. Well of course some couples have sex more than once a month, especially if they read this lube dispenser review to make sexy time even easier, but Valentine’s day is still a novelty.

Then again, if you’ve just started dating someone, Valentine’s Day is too much pressure. What if he thinks it means more than it does? What if it doesn’t mean enough?

And if you’re one half of an unhappy couple, this Hallmark holiday hits a nerve: Another year of not being in the relationship you always thought you’d be in. You may suffer a bout of brief, intense existentialist grief.

Basically, the only ones doing what you think the holiday is about (roses, chocolate, sex) are, if we want to get technical, people in the first 12 to 18 months of their relationship, who are still trying to impress each other, and guaranteed to get laid. Or, those blessed to be in one of those wonderful relationships where the magic burns for years. They’re rare, but they do exist.

Anyway, look, that’s not a LOT of people having sexy time today.

Valentine’s Day is not an exclusive club; it’s a holiday to celebrate love in all its forms, from the short, sexy bursts to the long, mellow partnerships, to the kinds of love we share with people we’re not dating. (Check out this study on how just being kind and loving to people at work is linked with improved productivity.)

But of course my heart is with the single people who see red at Valentine’s Day, and not in a good way. Here are the things I recommend you do and NOT do today:

1. Don’t hate. It’s not only pointless to hate on a holiday; it’s disingenous; like saying you hate money just because you don’t happen to have any. Don’t pretend that of all days, today you “hate” love because Valentine’s Day ruined it for you. C’mon. (That’s like “hating” gifts because you’ve had a few bad Christmases.)

If you like this post, you're going to love this workshop. Try it for $1. For reals..

If you like this post, you’re going to love this workshop. Try it for $1. For reals..

>>DO: Take a risk. You want something exciting? Try doing something exciting. One Feb 14th, I wrote a note on a cocktail napkin on slid it across a cafe table to a handsome thing. I never heard from him. Don’t matter. It was thrilling and empowering and kind (because though he never called, don’t tell me I didn’t make his day). I felt…romantic, without anything else having to happen. (Also: Read why you should be getting rejected more.)

2. Don’t go out with your girlfriends and dance in a circle. Sure, it’s fun. But the dopiest thing ever is when a bunch of single ladies who would like to meet potential mates do the one thing that will ensure they don’t: Turn in the lady wagons. Who-hoo! Girl power! No. This is dumb. Don’t form a big resentful clot in the middle of the room, telling dudes to talk to the hand. Why act like men suck, when, if we’re being honest, you’d like a nice one?

>>DO: Go out to meet people. If you’re smart, you’ll go out with just a few friends or, if you travel in a gaggle, split off and mingle. Or, forget the girlfriend outing altogether, and do something really bold: Go sit at the bar by yourself just long enough to enjoy a glass of wine. Remind yourself that you’re open to what may or may not happen.

(Afraid of getting rejected? Here’s why you should seek it out more.)

3. Don’t text your recent ex. I shouldn’t have to explain this. But, no matter how it ended, if you broke up within the past six months, steer clear. Of course, unless he has come back with a dozen roses and wants you back, and you’re happy about it. But if you both ended it for all the right reasons, going back now for a moment of comfort could cost you more later. (Read why you should unfriend your ex.)

>>DO: Go on a date with a stranger. Yup. I promise you, there’s someone online who’s free tonight. And don’t give me this crap about how it seems desperate. You can drop a line in the water and see if you get a bite. You don’t have to meet The One. But you can go out on one date with one new person, and say that on Valentine’s Day, you made an effort, and you had a reason to put lipstick on.

The moment when you’re headed out the door and the night is nothing but potential-that’s fun. And romantic. And brave. And way better than a margarita-sodden rendition of “I Will Survive.” Again.


If you like this post, you're going to love this workshop.

If you like this post, you’re going to love this workshop.

There are two reasons why you loathe dating: You’ve been out of the game too long, or you’ve been in it too long.

When you’ve been out of the game, you’re wary and wily and nervous as hell, because you think there are new rules, and you don’t know them.

If you’ve been IN the game too long, you think you’ve seen it all, and you haven’t had any luck (maybe because you’re relying on luck?), and either everyone else sucks, or you do.

Talk about a lose-lose situation. Because you can’t win: Either you’re not good enough, or no one’s good enough for you. And if you want to believe one of those things, or maybe even both, then you will be stuck, forever and ever, in that tidy little prison you’ve created for yourself.

Fact: The world is teeming with people. Single people. And many more become single every day.

Fact: Most of them are not psychopathic crazies who will stalk and kill you.

Fact: You are lovable, deserving of love, and yet you also do things that keep other people from getting close to you.

(On the run and want to listen instead? Your wish is granted:)

Tough Girl: A Case Study

I know a woman I’ll call Agnes who is tough, sassy, and sexy. She has no problem finding men who are interested in her, and yet she’s never really had a boyfriend. She’s been “seeing” this one guy we’ll call Mike for a few months. Though you wouldn’t know it, because NO ONE in her life has met him. She doesn’t invite him out in a group, but stops by “later”—and until very recently, had never stayed the night. They’re basically stuck in booty call city. And she is the mayor.

She asked me recently about a situation in which he was vague with his texts and she thought he was being “weird.”

“He’s being weird? YOU are being weird!”

I couldn’t help myself. But it was true! And she knew it. She had been treating him like a hookup and then wondering why he wasn’t exhibiting relationship behavior.

Um, because he didn’t know they were in a relationship, maybe? She hasn’t given him an inkling that she cares for him, wants people to know him, wants to, I don’t know, be seen in public with him?  I told her, “You have trained him to not expect much from you. So why should he give you anything?”

So instead of doing the guy pile-on, I came down pretty hard on her. Because while she may come off tough and sexy, I see right through that because I’ve worn that tough-girl facade before. (Read: How feminism f’d up my dating life.)

And, by the way, I wasn’t giving her a hard time because what she’s doing is “wrong” or that she should want or be something different. I came down on her because her actions aren’t getting her what she wants.

You want more from him? I said. Start treating him differently. You can’t treat him like a whore and wonder why he’s not acting like a boyfriend.

My point is this: It’s easy to think guys are the problem. But guys are pretty simple. The reality is that what you do, for a myriad of reasons, has often more to do with what you’re trying to protect than what you want. Often, because you’re afraid of what you want. Or more to the point, you’re afraid of being rejected, of being hurt, and all the things we spend our lives trying to avoid.

The catch-22 here is that the more you try to protect yourself, the less able you are to have what you want. Because loving requires risk.


So, yes, I created a workshop (“Stop Hating Start Dating”) precisely to address this and other issues that plague the modern dater. And it has nothing to do with apps or texts—those are part of dating, but they’re the puppet show that we use to enact our fears and expectations. You must address those first.

So if you want to reframe and reinvigorate your dating life, and own it in a new and empowered way, check it out.

It’s seriously low-risk—you risk $1. If after 3 days you’re sick to death of me and want your money back, so be it. We can still be friends.

(And by the way, it’s not just for ladies. It’s gender neutral in theory and application. But let’s face it, chances are, here as everywhere else on the planet besides the financial district, there are three ladies to every one dude.)