Judith Sills, Ph.d.

Straight Up Analysis, Straight Up Advice, Straight Up Psychology



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Getting Naked Again:
Dating, Romance, Sex, and Love When You've Been Divorced, Widowed, Dumped, or Distracted


Would I Sleep with Eisenhower?

It was all very unlikely. She was standing in the hallway of the Marriott Marquis Hotel, wearing cute wrinkled Nick & Nora cotton pajamas, the white ones with the cherries printed on them and the small ruffles at the wrists and ankles. She was deciding whether to knock on the door of a friendly colleague who, earlier in the conference, had patted her calf in a suggestive manner but allowed her to retire to her hotel room alone. He had seemed interested, definitely interested, though he had done no more than extend an indirect invitation and wait to see if she would RSVP.

But she was fifty-six years old, and it was more than twenty five years since she had responded to a calf rub offered by a man other than her now ex-husband. Still, that husband had been, for the last two years, rubbing someone else’s considerably younger calf—and wasn’t it ever going to be her turn again? That was the question that got her up, out of her hotel room, and into this awkward moment of indecision in a hotel hallway. Apparently, if it were ever to be her turn again, if she were ever going to kiss someone again, smile up at, hold hands with, not to mention the rest, well, something would be required of her. The new lover, new boyfriend, new companion, new man was not going to be delivered effortlessly into her life. At some point, she would have to knock.

So will you.

Because, however it happened, you’re back out there floating in single space. Whether you have been cast back out by painful circumstance, or you are finally back after years of hiding out, at this moment you are romantically unattached and on your own. And, by whatever process that has brought you to this brink, you are considering a return to the game.

That game would be the timeworn, thrilling, and terrible drama of flirtation, sex, and love; of courtship and romance; of getta-guy, getta-girl, or get gotten. How consciously and therefore how successfully you replay the game is the subject of this book. First you have to decide to knock.

You may be, at this moment in your life, very far from that hallway. Perhaps you are still frozen in the grip of a loss, staggering after a death or a betrayal. And even if your recovery from these wounds has brought you as far as this door, you may still be paralyzed in its face. The sexual and emotional experience available across the threshold is still far outside your picture of yourself. But you are considering a move in that direction. On the other hand, had it been a different version of you in the hallway, you might never have retreated to your room to think it over. You may be one of those who threw herself over that threshold and out of those damn pajamas twenty minutes after your last relationship ended. (Or, to be on the safe side, twenty minutes before.) You are trading partners, changing stories, and eager to avoid a hole in your heart or in your life. You have leapt headlong into courtship, perhaps without some of the strategies you’ll need to make it turn out better this time.

Most of us are somewhere between these two positions—wishing to reconnect in some important way, longing to have a little fun or a lot of sex or a great companion, but anxious, discouraged, or cynical about the possibility of happily ever after. Much as we have not given up on the fantasy of romance, affection, and love, we are undone at the prospect of reengaging in the tiresome and hurtful dating game that carries with it these rewards. Eventually, though, most of us wrestle with the reality: It’s the only game in town. All of us who are single—whether widowed or divorced, dumped or thankfully detached, or just newly resurfaced after the distractions of motherhood, career, or both—stand at the same anxious precipice. Must I, will I get back into the game of courtship? Would I want to? Can I bear its rigors? Is it worth it? Am I still a contender? Can I do it any better this time? Or at all? And, since it definitely requires two to play, where do I go to find someone with whom to get up a game?

These are legitimate questions at any age, but they can be showstoppers after, say, forty-six. That’s when we add the fretful salsa of age to our always conflicted feelings about dating. True, an amazing number of thirty-two-year-olds have been known to convince themselves that it is already too late. Old is not a belief confined to the “mature” woman or man. Too late is a destructive thought, whether at thirty-five or at eighty, but an awful lot of us over forty or fifty run it through our brains anyway.

For the moment, you are at your tennis club contemplating the decent-looking retiree across the dining room—single, sixty- eight, wearing whites and a knee brace—and you think, “Jeez, wouldn’t that be like sleeping with Eisenhower?” It’s a thought that could send you right off to babysit full-time for your own grandchildren, confining yourself to book groups and community service—all perfectly fi ne occupations if they are satisfying enough for you. But some of us stop to recall that, as it turned out, Eisenhower had someone on the side after Mamie apparently lost interest. We take another look across the dining room and see past the knee brace. We decide to knock.

Woman in Transition

Whether you are poised hesitantly at this brink or you’ve thrown yourself relentlessly, determinedly into the online, blind date, hookup bars middle of the middle-aged dating world, you are at a life stage you might think of as reentry. Reentry is a tricky time, and it requires more preparation and self-awareness than merely how best to market yourself with a great computer profile. (Though such advice helps—no question about it.) If you are looking for a safe and happy landing, reentry needs some solid-state understanding of the process and a damn good heat shield.

That is the purpose of this book. For one reason or another, you unexpectedly find yourself in the untethered universe of single life. To move from that romantic free fall toward a loving connection, you will have to navigate an intensely emotional, uncertain, and unsettling period of time.

The internal forces that will drive you during this period— your own individual fears and longings, your lifelong romantic patterns, and your acute reentry needs—are powerful, un- expected, and erratic. It would help to have some meaningful self-knowledge to steer a safe course. Yet your capacity for introspection and self-awareness may well have atrophied during your marriage or motherhood, when you focused so much on taking care of other people that you lost close touch with yourself.

Now here you are, thrown back on that self you may no longer know well, negotiating your own mixed feelings while you are recovering from emotional loss. Just catching up with your inner life could be a full-time preoccupation. But many of us are tempted to skip this inner step entirely. The outer drama of e-mail flirtation, social competition, and actual foreplay can be so compelling, confusing, or aversive that we miss a clear picture of ourselves because we are too busy watching the show.

That show, the interpersonal soap opera of dating, will involve meeting, assessing, kissing, touching, wooing, and negotiating with some stranger. And his children. Plus his friends. Not to mention his ex-wife, past girlfriends, medical history, financial fetishes, sexual aspirations, political biases, and his odd habit of saving string and old Playboy magazines because he still believes the collection is valuable.

Anywhere along this rocky way you might dismiss him, which will exhaust and discourage you, even though you are the one to do the dumping. Or he might reject you—which will sting even if you had already decided you didn’t want him. All told, it’s hard to believe that any one of us could refer to such a potentially brutal interaction as a game, nor that sane and self-sufficient adults would enter into it. But we do. And we must, because at the other end of reentry is connection, and that’s worth a lot of shake, rattle, and roll.

Actually, truth told, you will probably have to engage in bits and pieces of this process more than once, perhaps with many strangers, in order to develop one serious, solid, and cherished bond with a person who will undoubtedly turn out to be flawed, because in the end we all are. And then you will have the struggle to compromise and love him anyway. But by this time you will be long past the awkward uncertainty of getting naked again and into the serious relationship for which there are many other books written—some of which I’ve written myself.

Right now, though, you are at the precarious and interesting beginning. Between the relationship you’ve left behind and the new person with whom you will connect, there is an internal process and an interpersonal one. You can get better at both. The internal process of getting naked again involves a personal evolution. Understanding and furthering that evolution— its dynamics, conflicts, and their successful resolution—is the subject of part I of this book. It is also its deeper purpose. Certainly we date again because it’s a drag to sit home on Saturday night; because it’s nice to have a man to dance with at weddings, to open jars, or to intervene with the car mechanic; or because they sometimes pay and that’s a plus (though the cost of hair and makeup and shoes usually evens out this benefit). But expedience is not the only reason we return again and again to courtship, decked in hope and dread and fresh Botox.

Romantic life is really nothing more than a playing field; increasing your capacity to give and receive love is the prize. A sexual reawakening, some very good laughs, and the sheer pleasure of telling your girlfriends the tale are the side benefits. And happiness—packaged as quiet contentment, studded with emotional sizzle, and grounded in a sense of connection—is the point. To enjoy these fresh emotional heights, though, you will need more than a suitable partner. You need an evolving sense of yourself.

Most of us who get naked again start by shedding or losing a partner. We go from attached to alone, but that change of outward status takes awhile to percolate through to the soul. Naked can feel very chilly, and some of us rush to shelter in a quick new relationship, create a career onslaught, or take temporary, even necessary cover in the lives of our children. (A daughter’s divorce can, for example, distract you from the pain of your own.) But wherever you hurry to hide out, the change of identity will creep up. It’s best to be ready for it.

Even if you just stand bravely stripped and single in the world, it will still take some time to integrate the idea that this is you, meeting a strange man for coffee; you, handing cuff links to a man not your husband as you two dress after sex for a theater curtain; you, slow dancing at a resort party with a man who miraculously appears to have an erection. All the while the woman who lives in your mind’s eye is still married, a mother, a wife, a granny. Who are you now? Who will you become? Or more likely, if it’s fear whispering the questions instead of excitement—what’s to become of you?

Victorian as the thought is, it does capture the sometimes overwhelming sense of uncertainty that accompanies the transition from some safe harbor to the unsheltered world of single life. Over time, if you pay attention and press through the obstacles to change, this becomes you, free to decide whether to spend the money on the new roof or the trip to Africa; you, removing the dead mouse from the kitchen floor because there’s no one else there to do it and you know what, it’s doable; you, deciding to stay, move, buy, rent, with only your adult children to natter at you about your decision; you, slipping your business card into some guy’s pocket because at this point, why the hell not?

Getting Naked Again is about evolving into an adult single woman after you’ve defined yourself as part of a whole. It’s about partnering again, if that’s what you hope for, and about taking your clothes off in front of someone again, even if that’s what you fear. It’s about revealing yourself—your heart, your soul, your quirks and calcified habits, your physical droops, maternal missteps, crammed closets, and/or empty retirement funds—to fresh judging eyes. It’s about acting in your own self-interest, especially when your heart is steering you off the cliff of love, or when your fear has you dug deep behind a barricade of reasons. It’s about doing all of this with a smile on your face and a strong and clear sense of yourself, recognizing:

  • How the injuries and frustrations of your previous relationship shape your next one.
  • Which mistaken fantasies and beliefs you may be nurturing.
  • The signs that you are ready to reconnect.
  • Which of the two great reentry fears drives you.
  • Your most productive mind-set for dating.
In the end, like it or not, dating, commitment, and love are less about whom you meet and more about who you are. Part I of Getting Naked Again focuses on understanding who you are and catching up with the woman you’ve become.

None of that introspection is easy, especially because you’ll be seriously distracted. Though it may be rough, getting naked again is also an emotional rush. After all, you are not only going back to the game of romance; you are also returning mentally to the last time you played it. Circumstances have thrown you back on your own, to an earlier solitary time in your life. You are suddenly without cover, open to the cruelty of the seven second judgment, the evaporating e-mail friend. You are back to thinking about what to wear with an eye to how it unzips. Back to contemplating eyelash batting, phone-call waiting, and hope followed by crash followed by delicious, exuberant hope again.

In other words, you might be feeling the same wild mood swings and jailbreak giddiness you felt when you first left home. If you are coming back to life after a freezing grief, or a decade of grim marital endurance, you might just zip up a bustier, strap on your four-inch heels, and wallow in being young again for as long as you can.

But even if dating rituals make you feel temporarily twenty— with all its sexual thrill and shaky self-worth—it’s still smart to use your grown-up head to steer by. True, everyone goes back into the game in his or her own way, but there are common success and failure patterns from which you can learn. There are basic dating and relationship skills in which we could all use a refresher. More important, there are mistakes you can avoid, pitfalls to steer around if only you could see them coming. And, just as every satellite needs to align itself properly to assure a successful reentry, you will need to adjust your attitude to best survive the atmosphere of romance. Part II of Getting Naked Again, Interpersonal Expertise, reviews each of the central questions:
  • What’s the best meet-and-mate advice offered by people who have been out there and succeeded?
  • Who picks, who pays, who calls, who seduces in adult courtship these days?
  • How do you manage your girlfriends, their husbands, the social world, and altered family expectations when you turn single?
  • What are the four classic transitional relationships and what emotional needs do they satisfy?
  • How can you recognize, and correct, your own emotional regressions?
This might all sound like much ado about something that depends primarily on luck and the right social connections. In fact, most of us, whether we are dating at twenty-seven or seventy, tend to obsess about the question “Where do I go to meet someone?” and ignore the rest. After all, meeting someone is the necessary if not sufficient condition to a romance, and if you believe that no one is out there, then what good is knowing the best way to proceed? Too, “Where do I meet someone?” resonates with the cherished romantic belief that meeting the right person is everything, that when it’s right it’s right, that love solves problems.

Meeting is a critical part of the process. Whom you are willing to meet, how open you are to meeting, to connecting, to risking the rejection that so often follows meeting, how willing you are to do the picking, how much you rely on being the one picked—all of these are crucial relationship variables for you to examine and reevaluate.

You can’t ignore the meet-who-where question. But frankly, if you focus exclusively on it—that is, if you don’t look beyond the reasonable advice to —join clubs, ask friends for introductions, pursue your hobbies, be friendly, go where the boys are, but only if you’re sure you wanna be there, to take up golf or tennis or Internet matches, to try Elderhostel travel or Silver Seniors or Gorgeous Grandmas or some other equally chirpily named group you are apt to put out a great deal of effort with very little return. After all that work, with little love to share, you will naturally come to believe that there is no one out there, all the good ones are taken, no one you want will ever want you. In other words, without thinking more deeply about what you are doing, you could easily end up with all the self-limiting convictions that make so many of us retire to our sweat suits and curl up with our cats. Getting naked again, you’ve determined, was a bust.

Meeting someone is a numbers game, as you’ve been told.

But it is also more than a numbers game. It is bringing the right mind, body, and spirit to that numbers game. You are, after all, reentering after a long relationship followed by a brutal divorce (and they are pretty much all brutal, just each in its exquisitely individual way). Or you are gathering your strength to reengage after the death of a longtime partner—whether it was a partner you adored or one you tolerated and, if it was a long marriage, you surely felt some of each.

These losses might have been recent, in the last weeks or years. Or they might have been long ago, and you ignored the possibility of romance in favor of your career, your parenting responsibilities, your destructive addictions or elevating preoccupations. Whatever your individual pattern, when you reenter the game after age forty or so, you are different this time around. Your mind, your body, your emotional attitude will probably need a little conscious work, some weeding, some turning of the mental soil, before anything new can really take root.

It’s not all about whom you meet. Getting naked again is, first, foremost, and maybe in the end most important, all about who you are when you meet him. And that depends, at least in part, on what sent you back out there.