Singles: Patterns of Pursuit
There's a long path from one heart to another.
How to find your way through the meandering maze of dating.

A century ago, a 16-year-old Irish girl reluctantly arrived on Ellis Island, betrothed to a much older pub owner about whom she knew nothing. In love with a boy from her village, Bridget was devastated to become a New World bride. And though her husband was a kind man who stayed with her until his death, they never became close. She often let slip her lingering bitterness.

One hundred years later, my own experience of single life in New York City could not have been more different. Bridget, my great-grandmother, had just one ship ride between adolescence and marriage; I've had 15 years of dating. Her life was charted for her, her own feelings and wishes irrelevant. I had nothing but feelings and wishes to guide me. I had plenty of enriching experiences, but I also felt by turns anxious, rejected, guilty about rejecting others, and just plain lonely. I could choose unwisely, and there'd be no one else to blame. Autonomy is great, but it is not without its burdens. My tale concludes more happily than Bridget's: I have the luxury of looking forward to a life with my true love.

Somewhere between Bridget's arranged marriage and my protracted floundering lies a vast middle ground of single life that can be navigated happily, with an eye toward one's ultimate goal: often, but not always, a committed partnership. It takes only a few principles of human nature, and insight into one's own desires. While there's clearly no formula for how to meet The One, psychologists agree on beliefs and strategies that inadvertently hold people back. This is not to say that the uncoupled are necessarily doing anything wrong; they may just not have stumbled into the right cafe at the right time.

Nonetheless, it's worth taking an inventory of your romantic life. The successful single will be willing to turn a non-defensive eye toward his or her own dating patterns. Here I explore a few romantic cul de sacs that many singles encounter.

Dating Shake-Up #1: Get Out the *%*#$&(*# Door

Lady luck can seat you next to a gorgeous stranger at an open-air jazz concert. Watching TV in your living room, however, hardly facilitates serendipitous encounters. Putting yourself out there is a prerequisite to curing the loneliness that settles over you when you spend too many nights in.

Maybe you dread getting overlooked by people you'd meet if you were socializing. Or perhaps you're afraid that if you do get into a relationship you'll be distracted from other important goals. Whatever the hesitation, online dating could be a good way to get to know who's out there while maintaining control and privacy. Still, if you want to partner up, you'll have to get out eventually.

Ask a trusted friend to act as social coordinator—and simply promise to show up. Talk to someone openly about your self-perceptions to see if they match others' ideas of who you are. Take on new work or extracurricular challenges to increase your self-esteem and your confidence that you can handle the pressures of the singles scene and are an attractive addition to it.

Snapshot of the decision-making center of a twentysomething's mind at a dinner party: "The girl sitting next to Chris is friendly, and she's a politics geek, just like me. But there's that speed-dating thing at the brewery next week, plus I haven't written back to that blonde I met online last Thursday...."

Barry Schwartz, a professor of psychology at Swarthmore, has shown how gluts of products paralyze consumers, and he's convinced that dating overload can similarly hamstring singles. "The temptation to not choose is great in a world where there is a large number of options," Schwartz says. He advises shoppers to settle on "good enough" purchases, but finds it much harder to convince singles to apply the strategy to their love lives. "People think they need to find the absolute 'best' romantic partner for them," Schwartz says. " But I believe that making a commitment is an act of faith. If you wait until you're sure, you'll die alone."

Even if you're not too picky, you may consistently fall for people who aren't right for you. You're attracted to bad boys or girls—a shot of adrenaline into a routine-filled life, but a letdown when you need a dependable companion. Or you gravitate toward quiet types, but soon enough feel frustrated with their lack of verbal input.

We learn how to relate to people through our family members and other significant relationships in early life. Sometimes those relationships aren't easy or healthy, but they are what we know. We may have even developed a role to fit into our clan—say, the overachiever or the peacemaker. Say you were the charmer in your home, the one who pulled everyone else out of dour moods. If you were to meet a man who needed constant bucking up, you'd be comfortable and quite effective. But just because the arrangement would feel comfortable and familiar doesn't mean he'd be a great partner who could support you emotionally.

You may even be attracted to particular people out of a desire, conscious or not, to rewrite bad endings. Chicago therapist Wendy Wasson recalls a patient who had a critical, judgmental father. The patient began dating someone who was accepting at first. But when he became distant and negative, she was suddenly desperate to please him. She wasn't consciously aware that her boyfriend shared traits with her father, but Wasson helped her see that on some level she was trying to rework that family dynamic by winning the man over.

If you're not sure whether you have a misguided yen for a certain type, list your past sweethearts' prominent traits. While you're at it, write down ten qualities that describe your ideal relationship. Instead of a grocery list of what you want in another person (blue eyes, likes hockey), this should detail what you value and what you most want someone else to bring out in you (we would hold each other to our goals, we would laugh frequently).

Psychologist M.P. Wylie, a relationships coach, puts clients through this exercise to remind them that all pairings are a pas de deux of personalities. It also encourages people to separate real deal-breakers (doesn't want kids) from nitpicky requirements that might screen out true love. You say you require a college grad, but what if you meet an ambitious autodidact who doesn't have that piece of paper? He or she might fulfill your desire for a partnership that fosters intellectual growth, even though the person wouldn't meet your checklist.

Nicole had been daydreaming about their third date when his email popped into her inbox. All week she'd built up an ironclad case for why he was perfect for her, and marveled at how their interests dovetailed. Her friends were going to be so impressed!

The message was an unaffectionate request to reschedule. She felt a surge of anger: How could he act like this? Why wasn't he at least excited to see her? She'd set herself up for disappointment because she expected him to conform to her fantasy, and not the reality—they barely knew each other.

Moving too fast, either by projecting hopes onto someone or by speeding up a natural getting-to-know-you phase, skews your ability to objectively judge a prospect.

"If attachment is the glue in relationships, then an accelerated attachment is like super glue. It activates a willingness to overlook and minimize obvious problems, it blinds your vision, and it intoxicates your emotions and hormones so that you feel safe and secure in this newfound love," proclaims psychologist John Van Epp in his book How Not to Marry a Jerk.

In the early stages of romance, it's wise to make non-date-related plans that are as exciting to you as your prospective partner is. And mom was right: Don't jump into bed right away. Sleeping with someone prompts your brain to release neurochemicals such as oxytocin that spur bonding and make you feel more connected to and dependent on your bedmate than is wise at an early juncture. The bonding phenomenon is stronger for women in general, though men who have been without someone for a while can also become overly attached to a new  sex partner in the absence of genuine affection, Van Epp says.

Once you know you can truly trust a dating partner, sexual intimacy can strengthen the connections you've already forged. But if the physical aspect of the relationship swamps your total time spent together—ideally in a variety of situations—you're at risk of ending up with someone who won't be good for you in the long run.

You're probably marshaling counterevidence in the form of happily married couples who slept together on their first date and who are convinced that the amorous fast track had no negative impact on the ensuing relationship. That's great for them, but if you want to aim for better relationship outcomes overall, consider waiting it out.

One of my friends stopped dating a smart, sweet, beautiful woman after discovering she possessed, of all horrors, a Celine Dion CD. Another friend continued seeing a guy for six months even though he conducted lengthy phone calls with his ex and other women in front of her.

Assessing a partner's worthiness is part art, part science: You must measure and weigh a constellation of quirks and qualities without losing sight of the whole person. How can you tell whether a single incompatibility is a deal breaker or an annoyance worth tolerating? Keep your eyes open for behaviors that signify distasteful and deeply-rooted attitudes. Don't rationalize consistent displays of disrespect or irresponsibility—observe them carefully. Such bad behaviors will only get worse over time, when people are no longer out to impress you. The best marriages are the ones preceded by happy dating relationships, so take your partner at face value and don't expect situations to magically improve over time.

However, it's only fair to raise your concerns to your partner, and to give him or her a chance to change. Within a healthy relationship some behaviors are moldable. Gently bring up the issue ("sometimes it seems that you're not listening to me when I tell you stories") in order to put it into what Van Epp calls the "machinery" of the relationship. Your girlfriend may need to be reminded a few more times of her habit of spacing out while you talk, but it's possible that after that, she will become a rapt listener. If you catch her daydreaming three or four more times, however, you have your answer as to whether or not she is capable of tuning in. You then must decide if you can live with that trait or not. If you can, discipline yourself to not get upset at the behavior, since you decided to put up with it.

While it's a vital first step, understanding the patterns in your behavior isn't enough. You must continually make yourself do what doesn't come naturally. It's comfortable for you to reject short men. So say yes to the next one who flirts with you. It's easy for you to become overly dependent on new boyfriends, texting them every hour. So hide your phone and resist the urge. It's tempting to cut things off before your new love starts talking about "the future"—so bring up the topic yourself.

Consider a woman who was magnetized by macho men. Her alluring suitors quickly morphed into angry jerks. The consequent fights and breakups were devastating, and yet they never deterred her from going back for more with a new tough guy. Van Epp encouraged her to accept a date with a sensitive young man. Her mission was to expand her comfort zone: Even if it didn't work out, she'd be more open to prospects like him in the future. She began spending time with him, and he didn't thrill her. But she stuck to it and paced the relationship well, forgoing sexual contact. After a few months, she developed intimate feelings toward him that finally blossomed into a physical attraction. After a year, she fell deeply in love and married him.

Not all experiments in pattern breaking work out so well. Even after you've changed your counterproductive tendencies, you may still get your heart broken. In the face of such disappointments, you must be careful not to beat yourself up or write off every last member of the opposite sex.

Being single longer than you'd expected gives you the opportunity to find your way through a variety of entanglements and to understand how different sides of yourself emerge based on how you conduct your relationships and whom you choose to get close to. It also gives you the chance to build satisfying friendships.

"When singles realize that they need to take responsibility for themselves, they often feel empowered," says Wasson. "And learning to appreciate other emotional bonds helps them build resilience."

Wasson, who was single for much of her life, notes that when she met her partner in her 50s, he truly valued the life she had built for herself. It was, in fact, part of her appeal.

Wasson encourages single men and women to throw themselves into life when they least feel like doing so.

"If you take out a mallet or get cynical, it keeps you from moving on," Wasson says. "Staying confident is, after all, what attracts people."

In retrospect, although it wasn't always pleasant, being single lent me precious time to make and nurture a wealth of friendships. I might not have forged such strong bonds had I not needed dating advice and support. In this sense, my romantic quest was worthwhile in more ways than one. —Carlin Flora

A commitment-phobe might fear the end of youth, or he (yes, they are often, but by no means always, male) may just be itchy at the thought of a long-term vow. They are not likely to identify themselves as having commitment issues, however, since in their mind there is always a good reason not to move forward with a relationship. Their stasis breeds misery on both sides: The commitment-phobe is paralyzed and his or her partner is left feeling hurt and rejected.

The Plan:

Life sometimes catapults even the most reluctant lover into commitment: Advancing age, housing logistics, or a recognition that the perfect has become the enemy of the good can all reform the staunchest commitment-phobe.

"Sometimes it's easier to leap off the cliff than to walk slowly down the diving board," says psychologist and writer Judith Sills. Many people would be happier eloping than dragging out wedding proposals and plans.

Marriage is a big decision, but it doesn't determine everything that happens thereafter. "We don't make mistakes," says Sills. "We build or create mistakes over time." Paradoxically, the reluctant party's relationship may get much better after he takes the leap. This leaves commitment-phobes locked into a self-fulfilling prophecy: They don't feel passionate enough toward someone, so they break up and then think, "Thank God I didn't commit to her!" But if they had committed, the passion might have flowed after the fact.

There's at least one broad exception. Charles Waehler of the University of Akron found that middle-aged bachelors who are unsatisfied in life and ambivalent about marriage remain conflicted after marriage.

Single parents often fear that their desire to find someone will lead them to overlook their children's needs or feelings. They wonder how their kids will react, and how all of the moving parts of their family and their prospective new love's family will fit together.

The Plan:

Block out a privacy zone, counsels Sills. Kids don't need to know dating details, and they certainly don't need to be confronted with any aspect of their parent's sex life.

When someone is important enough to be introduced to a child, the parent should have him or her over for dinner. But they shouldn't stage-manage. Let everybody find out about each other naturally. And the parent shouldn't do a post-mortem on the encounter, warns Sills. "Sometimes when we put things into words we get committed to a point of view about someone."

Bringing home a new dating partner may very well stir up children's fears about divorce or death or the future. The important thing is to let the kids have such feelings. They will adjust to the situation over time.

And avoid the "pseudo-marriage" trap: If you've been married, it's tempting to rush into sharing lives and household duties with someone. But this can put undue strain on a budding relationship.

Younger singles searching for love often look to midlife and beyond with a marked fear that they will still be alone. But midlifers often find the experience of being single easier than it was during their reproductive years, when they may have felt dramatically out of step with married friends, says Wendy Wasson. Suddenly, they're forging new connections with peers who are divorced or widowed.

The newly single camp can be more difficult: People feel like failures after the breakup of a long partnership, or undergo a lengthy grieving  process after having experienced a partner's death. Yet Wasson sees a bright side: She's witnessed patients develop a renewed sense of vitality and optimism after a panicky adjustment period. People—especially women—often reorganize their lives around friendships (old and new) and look forward to a more independent and open-ended way of life.

The Plan:

Broadening one's horizons is not just a pragmatic way to approach the social scene; it's also the key to finding unexpected happiness  in midlife. In her book Getting Naked Again: Dating, Romance, Sex, and Love When You've Been Divorced, Widowed, Dumped, or Distracted , Judith Sills argues that older singles should consider a wider range of prospects, since they're not looking to create a family. " It doesn't matter if a woman shares your religion, for example, if you're not raising children together," she says. Sills says that women concerned about the lack of available older single men, for example, should not evaluate men they meet in terms of whether they are marriage material, but should rather enjoy and embrace what they do have to offer—be it friendship, companionship, help, or guidance in cultivating new hobbies or interests.

Middle-aged singles may find that the autonomy and social skills they've built up over the years give them a confidence in the world that they never had as young people. In fact, several interview-based studies of single women aged 40 and above revealed that they felt a greater sense of clarity and agency than ever before. They'd managed to fulfill their needs to nurture others (perhaps via nephews and nieces) and to feel supported (often by strong friendships and family ties). Furthermore, they were freer to express themselves since they no longer felt constricted by expectations about marriage that may have once sparked regrets or insecurity.

By Carlin Flora, published on July 1, 2009 - last reviewed on November 20, 2015