I have heard there are people who actually enjoy dating and being single. I don’t know who these people are or what planet they come from, but I certainly was never one of them. In my late twenties, I broke up with a perfectly nice long-term boyfriend to move halfway across the country, where a promising job awaited. There I ended up dating and being single for four years before I met my future husband, and basically it was horrible, horrible, horrible the whole time. I hardly need to catalogue the series of woes I endured, as they are doubtless familiar to all. The loneliness. The disappointments and dashed hopes. The rejections. The constant self-doubt. The physical exhaustion from going out all the time. The insultingly overpriced martinis.


Bridget Jones, heroine of the eponymous novel, who embodied a decade’s dating angst, divides the world into the two opposing camps of Singletons and Smug Marrieds. I am now among the latter, but I haven’t forgotten where I came from. So I wanted to propose the following points of advice for those who are still back there. My expertise comes from experience and suffering, and also from having read some dating advice books and having a B.A. in philosophy. You who love being single can stop reading now and go back to pretending you didn’t grow out of a pod.

1. Jettison all pride and embrace your desperation.

The temple of Apollo at Delphi in Ancient Greece was said to have been inscribed with the saying gnothi seauton, or “Know thyself.” I believe that this precept is every bit as central for dating as it is for finding Socratic dialectical enlightenment. The reason I’m bringing this up is that a lot of single people who don’t enjoy being single seem to feel they ought to, and have a hard time admitting the truth, even to themselves. They have been conditioned to think they should be independent and devil-may-care about the immatrimonial state that leaves them eating a grilled cheese sandwich for dinner while standing at the kitchen sink every other night of the week, since it is clearly too much bother to cook or do dishes for just one person. They fear they will be seen as desperate and pathetic if they admit to anyone, even themselves, that they honestly would prefer to be companionably installed as part of a live-in couple, with real motivation to cook actual meals, or at least to go out of their way to get the good take-out.

To make matters worse, there is a pernicious doctrine afloat in our society, according to which if you aren’t happy already by yourself, being in a relationship isn’t suddenly going to make you happier. This seems to come from the same people who brought us the slogan “What doesn’t kill us makes us stronger,” and is equally questionable. My experience suggests the opposite, that if someone is longing to be in a relationship, there is an excellent chance that being in one could make that person happier.

A corollary to that pernicious doctrine is that if you look desperate and pathetic, you will be unattractive and no one will want to hang out with you, while on the other hand if you seem happy and content with your independent, devil-may-care single life, you will be a magnet for members of the opposite sex (and potentially for members of the same sex as well, if that is your goal). The problem is that if everyone goes around looking delighted with their single state, it makes it impossible for anyone who’s secretly discontented to tell who else is secretly discontented and who therefore might be receptive to their overtures.

It also fosters widespread passivity. People who buy into all this rigamarole about being secure in your single self end up too busy trying to lead fulfilling, productive, non-desperate lives to take the very steps that can help them escape that frenetic existence. They are too busy working on their careers and training for triathlons and perfecting the decor of their chic one-bedroom condo to even think about asking someone out or calling someone they like to spend lazy hours on the phone with said person talking about nothing. Instead they expect that love will randomly drop down on them someday like a brick falling from an apartment balcony onto some poor unsuspecting passerby’s head. Presumably some very assertive, yet contradictorily non-pathetic and non-desperate person will one day take them in hand and lead the way, and fate will do all the heavy lifting.

The first step out of this mess is to make a frank and totally honest assessment of what one wants—and if that means acknowledging one is genuinely desperate to exit singlehood, then the only honest course of action is to jettison all pride and embrace one’s desperation. Of course, if what you really want is to construct models of major European architectural landmarks out of popsicle sticks, well then, it’s good to have decided that, and at least you’re not wasting anyone’s time by going on outings that don’t involve frozen desserts. Or maybe this earnest self-examination reveals to you that all you really want is casual, non-committal sex with a large number of partners, or to be a serial robber of banks, or perhaps a heroin addict. Fine, although I can’t give you any advice, there. But if you look inward and find that you really want a stable partnership with a loving companion, my advice would be to take this realization and run with it, and not to be too concerned about whether or not that counts as desperate. By “run with it,” I basically mean:

2. Take risks.

During my angst-filled single years, I encountered at least two major schools of dating philosophy that strongly discourage their adherents from taking emotional risks. One is “The Rules,” derived from the book of the same title published in the nineties and directed chiefly at single heterosexual women. The Rules seem to have something of a masculine counterpart in the reams of dating guides aimed at men describing how to seduce and bed women at the fastest possible clip.

The main gist of The Rules is that women should be as passive as possible in relationships and try to appear totally uninterested in men. They should be mysterious and sphinx-like, not being overly friendly or talkative at first and rarely if ever returning phone calls. They should never pay for dates or open their own door, and should let the man do all the work. They should also keep in shape and lead busy, non-pathetic-seeming lives, although they are never, ever to leave the house without lipstick on. This counterintuitive relationship quietism is advised on the rationale that men prefer to hunt women down like prey and indulge their inner micromanagers by being in charge of every single step of the courtship process. Never mind that history, literature, the movies, and everyone’s anecdotal files are replete with examples of women who made the first move or were otherwise less than demure and yet managed nevertheless to land in reasonably worthwhile relationships.

What the advice boils down to is that the woman should let the man take all the risks and put his ego on the line at every point. In this way, if he manages to make any progress at all, he will be so emotionally invested that he will not want to give the woman up even if she turns out to be, rather than mysterious and sphinx-like, inanely chatty and obsessed with finding the right shade of lipstick.

The male answer to The Rules, which I fondly like to call the seduce-o-matic approach, encourages men not to fall for such passive-aggressive romantic tactics, but rather to turn the tables on Rules Girls by being aloof and roguishly intriguing. At the same time, the would-be Casanova is often advised to hit on every woman he meets, since getting laid is a numbers game and he is bound to win at some point through sheer persistence. While indiscriminately hitting on passersby might seem like risk-taking, the real point seems to be to invest as little emotion per person as possible, so as to be able to move on to the next conquest with maximal efficiency.

The other philosophy I mentioned above, which is really more of a non-dating philosophy, is the so-called Hookup Culture that has had so many conservative panties in a bunch over the past decade. I have read several studies of the phenomenon, but didn’t experience it during the heyday of my youth, since I attended a very strict religious college and then an endless graduate program during which I was so busy being neurotic that I wouldn’t have noticed a hookup opportunity had it socked me in the eye. I did become somewhat familiar with the mentality, however, during my personal Long March across the forbidding and arduous terrain of dating. For example, there was the time I was summarily dropped by a younger twentysomething guy for not having sex during our second rendezvous, with Mr. Hasty explaining that “you have to get your booty in before you get to know the person and find out you’re incompatible.” With that, I believe, he aptly summed up the ethos of this culture, or absence of same. Again, the approach seems to be to extract with maximal efficiency the nuggets of physical pleasure from interactions with members of the desired gender, with as little emotional and social risk as possible to the extractor.

What gets to me is not so much the casual flinging around of intimate acts like old socks into the laundry basket, or the reverse, the claustrophobia of one-size-fits-all dating Rules that reduce every step of increased physicality to a power struggle lost or won. What really gets to me is the bleak cowardice and spiritual inauthenticity implicit in all this dancing around on one’s tiptoes and contorting oneself in increasingly bizarre ways as if in a metaphorical game of limbo dancing, all in order to avoid emotional risk. I find myself wondering when relationships started to become all about not getting to know someone and not having feelings for someone. When did relationships become all about not relating?

Emotional risk in dating is a lot like financial risk in investing. If you try to play it too safe in your investments, whether emotional or financial, you won’t beat inflation over the long haul (the dating equivalent of inflation being age, perhaps, if not cynicism). Prudent investors don’t get caught up in real estate bubbles or irrational exuberance, but they also don’t squirrel away their funds in a passbook savings account (except maybe during a wicked recession, and even then, not indefinitely).
In any case, all the honesty with yourself that you might gain by Socratic soul-searching and embracing your desperation in accordance with point one, above, will be worth nothing if it isn’t followed up by equally honest actions. If honesty towards yourself tells you that you want to be with someone, you have to go for it, even if that means taking risks. Take the risks judiciously and with all the savoir-faire and sophistication and moral perspicuity you can muster, but take the risks. Depending on your case, this might mean going to an astonishingly cheesy-sounding singles event, or calling your crush and asking her or him out, or bringing flowers to a dinner date, or tearing off your clothes and diving into the sack with someone, or turning down sex because you want love first, or confessing feelings, or proposing marriage, or just caring limitlessly about another human being. Regardless, the risk must be taken. The alternative is to be cowardly, ungenerous towards others, stingy in filling your own psychological needs, and inauthentic in your mode of existence. And do you want to be those things? I should hope not.

3. Be lucky.

Preferably very lucky. You may have noticed by now, but dating is no meritocracy. Plenty of ugly, dumb, socially graceless, height-and-weight-disproportionate, and even Republican people are in stable, lasting relationships, wallowing in smugness and having frequent fantastic sex. Even those people who do medieval reenactments, even they end up finding life partners and getting married in strange Wiccan ceremonies and living happily ever after, singing lusty ballads and eating giant barbecued turkey legs together as they practice for the next jousting competition. Even downright mean, alcoholic, and abusive people clearly must manage to woo and win mates, or there would be no such thing as spousal abuse and no one to go on Oprah. By the same token, among the ranks of the unhappy single you will invariably find good-looking, highly educated, articulate, talented, morally upright, wealthy, triathlon-ready men and women. The dating gods are capricious and unfair.

Finding a long-term romantic partner is akin to setting a tsunami in motion, in the sense that the number of variables that determine the event is vast almost to the point of infinity. In the tsunami’s case, it might be a fluttering of butterfly wings in the other hemisphere that gets things going, or the millions of individual choices that spur global warming (did you drive your car to work today?) In the case of a marriage, it might be that you just happened to be at Safeway one Tuesday at 5:43 p.m., even though you normally shop at Albertson’s, but you were passing by and you saw a sign about a cheese sale and decided to stop because you were low on cheddar for your grilled cheese sandwiches, and then you just happened to reach for the same block of cheddar as your future husband, and that particular block of cheddar wouldn’t have been sticking out so prominently had it not been for the fact that the lady who set up the cheese display was new and so the cheese pile wasn’t quite as symmetrical as it should have been, and the reason she was new was because she got fired from her old job at Wal-Mart when some rebellious teenage punk tripped her and she lost her temper, and the reason the teen punk was so rebellious that day was because his girlfriend just overdosed, and the reason she overdosed was because she happened to go to the wrong dealer and got stronger drugs than usual, and the reason her usual dealer wasn’t there was because he was down with a cold, because some 60-year-old lady with blue hair sneezed on him on the bus. And if it weren’t for that blue-haired lady sneezing on the bus, you would never have met your husband and your six kids would never have been born.

Anyway, you get the idea. If there were really a dependable method or set of rules that worked to help people find love, all of the smart, worthy people would be in relationships and would be strutting around with smirks on their faces like George Bush in a flight suit. Since that isn’t the case, we can conclude that luck and stochasticity play a considerable role in determining who hooks up for the long haul and who is stuck making the grilled cheese sandwich.

The good thing about this is that you don’t have to feel like it’s necessarily your fault if you take risks and make an effort to be with someone and it still doesn’t work out. Instead, you can curse and rail against fate, and channel your disappointment and bitterness into depressing poetry and clever postmodern craft projects. However, the bad thing about this is that you might then think that it’s pointless to go to all the effort in the first place of embracing your desperation and taking risks, since you could do this till the cows come home and potentially still not end up with anything but grilled cheese. After all, we have just made the point that the dating gods do not necessarily help those who help themselves.

But to that I say that even if there is no guarantee that making this kind of effort will actually get you anywhere, it will still have psychological benefits. You will like yourself better, if only because you behaved in a morally courageous way. And at least you will have ruled out the possibility that your loneliness was the result of you sitting around twiddling your thumbs and not trying to do anything about it, and that will make you feel better about yourself, too.

4. Bask in the smugness while you can.

There are only so many moments of pure, unadulterated smugness that each of us will have in this life. My advice is to seize those moments and milk them for all they are worth. When you finally get that big stroke of luck and meet that spongeworthy someone, there is often a temptation to give in to your feelings and wear your heart on your sleeve, engaging in conventional campy behavior: public displays of kissing and holding hands, looking meaningfully into each others’ eyes, calling each other by pet names, using baby talk, gratuitously spending large amounts of time together. This is a temptation you should give in to.

Most mainstream dating advice will tell you the opposite, that you should resist such temptations with every fiber of your being, because that sort of uncoy and openly affectionate behavior is a sure ticket to making your lover think that you actually like him or her, which inevitably spells doom. Once a girlfriend gets a whiff of non-aloofness, so the thinking goes, she will turn tail and run, and similarly if a man comes to the conclusion that he hasn’t seduced a woman totally against her will, he will suddenly be nauseated by rather than attracted to her and will drop her like a hot potato.

It may be that some people are indeed going to react with horror when their affections appear to be reciprocated. However, the people who react with horror are precisely the ones that you want to weed out of your pool of potential life partners, and basking in smug coupledom is a convenient way to do the weeding, with the added bonus of being enjoyable in and of itself.

If you have a lot of single friends when you luck your way into smugly encoupled status, you might get a few protests here and there. They just don’t want to see you holding hands or gazing enraptured at one another, or they resent that since you’re now having two-hour phone conversations with your significant other every night they can no longer reach you as easily. Or they subscribe to one of the previously discussed schools of dating philosophy where restraint and subtlety are the guiding ideals of every fledgling relationship, and there are certain rules and expectations, like that you’re not allowed to meet his mother until you’ve stopped using condoms, and he can’t meet your friends until you’ve met his friends, but conversely you can’t meet his friends until he’s met yours, leading to the famed Snufflupagus Syndrome in which none of your friends and family members ever believes you really have a partner. These single friends may end up dropping you hints to the effect that if you hold back a little on those displays of affection they might become more meaningful, or other similarly ardor-extinguishing advice.

Of course, soon enough, in most long-term relationships, the lovey-dovey stage passes, and soon enough, you will not be holding hands anymore everywhere you go; instead—if, say, you have kids—your hands will be full of things like sippy cups and snotty tissues and a smelly diaper bag. Even if conjugal passion remains undiminished, it can still, over the years, change in its outward form into something less obvious—so that to outside eyes it might look an awful lot like general chumminess punctuated by bouts of grouchy bickering and the occasional surreptitious ass-grab. For that reason, the wise thing to do is to bask in the smugness while you can and enjoy the hand-holding for as long as it lasts. If your friends are equally wise, they will understand and even encourage you in this.

5. Don’t worry too much about being taken in.

It seems that in dating there are people who worry quite a bit about being taken in, or deceived in some way by the object of their interest. Physically, emotionally, or financially, there is a putative risk of being used or taken advantage of, for example, if the other person pretends to be interested in the longer term, but really only wants a short-term fling, or fakes an interest in one’s whole being, but is really only interested in a small part of it, like the wallet or the genitals, or the person snookers you into some sort of implicit or explicit pact of exclusivity and then cheats on you. Perhaps as strong as the fear of being deceived by the other person is anxiety over the risk of self-deception where these things are concerned.

This fear of being hoodwinked appears to be a big driver of bad dating and relationship advice, like that you should pretend not to like people so that they will like you more, and that you should try to maintain a glacial pace of progress and frosty emotional atmosphere in the early stages of a liaison (defined as the first ten years or until at least two children have been born).

It must be acknowledged that there are genuine risks involved in dating, and clearly one should use every means at one’s disposal to prevent the worst possible outcomes, like date rape, theft of personal property, infectious diseases, crack-whoredom, and human trafficking that causes you to end up as a sex slave in Dubai. There is also no doubt that being cheated on or other griefs and hardships and humiliations stemming from a severed relationship can be brutally hard to bear. Still, loving and being loved is a basic, if far too often unacknowledged and unfulfilled human need, and that means that a lot of people out there are looking for the same thing you are (even if you don’t count the one percent who are statistically likely to be psychopaths). So, while you shouldn’t not worry at all about being taken in, you also shouldn’t worry too much about it.

Even though I am not a Christian, I find a good deal of wisdom on this subject in an essay by Kierkegaard on the ideal of Christian love that “believes all things.” Kierkegaard writes:

All men have a natural fear of making a mistake—by believing too well of a person. However, the error of believing too ill of a person is perhaps not feared, at least not in the same degree as the other. If, then, we are not most of all afraid of being in error, we are nevertheless in error by having a one-sided fear of a certain kind of error. It puts a crimp in vanity and pride ... to have believed too well of a swindler .... One is peeved with himself, or one finds rather that it is “so stupid” to have been fooled .... Yet should it not occur to us, to speak mildly, that it is just as stupid to have believed ill, or mistrustfully to have believed nothing where there was good?

In other words, we tend to be very afraid of putting too much trust in someone who doesn’t deserve it, but not nearly afraid enough of failing to put trust in someone who does deserve it. In this way, we run the risk not so much of being cheated, but of cheating ourselves out of potentially worthwhile relationships. Kierkegaard writes: “And yet, even if one is not deceived by others, I wonder whether he is not deceived anyway, most terribly deceived, precisely by himself, by believing nothing at all, deceived out of the highest, out of the blessedness of devotedness, out of the blessedness of love!”

The philosopher goes on to say:

One cannot deceive the true lover ... for to deceive him is to deceive oneself. Indeed, what is the highest good and the greatest blessedness? Certainly it is to love in truth; next to this, to be loved in truth. But then it is impossible to deceive the lover.... If it were possible to deceive someone in money matters in such a way that the so-called victim kept his money, would he then be betrayed? This is precisely the case here. By his attempt the deceiver becomes contemptible, and the lover [remains] in possession of the highest good and the greatest blessedness—therefore he certainly is not deceived! The deceiver, however, deceives himself. He does not love, and thereby he has deceived himself out of the highest good and the greatest blessedness. The next highest good is to be loved by one who loves in truth.... Again the deceiver is on the way to deceive himself out of this, too, insofar as he prevents himself from having the true benefit of it and insofar as he should succeed, when his deception is eventually discovered, in wasting the other person’s love and making the lover unhappy by his ceasing to love truly—instead of remaining in love ... secured against deception.

Now, some might quibble a little with the ordering of priorities here, perhaps reversing the ranking of the top two values of loving and being loved. Even so, the point largely still holds, and this is a useful perspective to maintain in dating generally, as well as a consoling thought for when things go badly.

6. Whatever you do, don’t give smug married advice to the single.

Through some variant of Murphy’s Law, giving advice of the sort I have just given appears to be a sure route to divorce and public humiliation. One of the women who co-wrote The Rules ended up divorcing her husband right around the time her marriage advice book came out. And the once hallowed Dr. Phil now seems to face more or less constant rumors of affairs and impending divorce. So, in sum, I hope all you single people out there appreciate the sacrifice I’m making for you here.

Good luck, and may you soon be smug.