You’re either in it, or you’re not. And if you’re in it, then it’s a veritable black hole of platonic interactions and nearly there interludes. I’m talking about the friend zone – the inescapable territory for nice guys and girls everywhere.

People are either friends for life or romantic prospects and, once set, those definitions are nigh impossible to escape. If you haven’t been held back by the friend label, then you’ve probably tried to enforce that barrier on someone else. Regardless of which side of the line you’re on, negotiating that boundary is always awkward and often complicated. So to ease the stress, here are some tips to lead you through the treacherous track.

SCENARIO 1: A total hottie comes to be part of your circle of friends, but the vibe between you is more friendly banter than flying sparks.

DO ask for some one-on-one time. Suggest something innocuous like coffee or lunch where you can be comfortable yet intimate. See if that cutie lives up to your expectations and if there’s potential for something more than friendship.

DON’T plan a candle-lit dinner. Go slow, or risk appearing too intense. Another no-no: getting drunk to loosen up around your crush. Slurring is always a turn-off, and you’ll just come off as unattractive and immature.

SCENARIO 2: Congrats! You’ve met that special someone. Too bad it’s your long-time friend who looks at you like a sister.

DO assess your emotions, and determine if they’re worth the gamble – disclosing your feelings might add undue tension. But if you must, do so gently in a casual setting. The truth goes a long way. And at the very least, your friend will be flattered to know you care.

DON’T blindside your friend with an over-the-top confession. Make the reveal as comfortable as it can be. But remember to be kind to yourself, too. Don’t bottle up your feelings just because you want to preserve the friendship. You never know what could happen if you never try.

SCENARIO 3: Your dating drought finally ends with an invitation to dinner. You’d be more excited if it wasn’t from a friend of a friend for whom you have no interest.

DO be open. One date won’t hurt, and your suitor might surprise you. But if you’re sure it’s strictly friendly, be polite with a definite no. There’s nothing worse than unintentionally leading someone on just because you’re trying to be nice to a friend’s friend.

DON’T act embarrassed after declining. Keep the rapport pleasant since you’re bound to see each other again when hanging out with your mutual buddy.

SCENARIO 4: Your BFF makes a move on you after 10+ years of friendship. You like things the way they are, but you don’t want to strain the relationship.

DO be honest. You owe your best friend the truth, even though it may be tough to hear. And give your friend time afterward, if needed, to cope with the refusal. Rejection is difficult, especially when it comes from someone so dear.

DON’T freak out. Though easier said than done, remaining calm and as un-awkward as possible will save your friend some face. Don’t ignore the situation either. It will only aggravate your relationship with that person in the future.

photo by ana kunst

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As a generation of overachievers, we feel entitled to have the perfect life the moment we envision it. Everything must be accessible at the speed of a mouse click, and the lives we embark on must provide a clear route to our future. Gen Y has no patience for ambiguity, and this includes our personal lives. Courtship has always been one huge gray area, especially in its beginning stages when we don’t know where the flirtation is going. So to allay the stress of the unknown, we have those infamous DTRs – the “define the relationship” talks. But what do those talks really mean? And if we’re confident in our feelings, are those labels really necessary?

The always awkward talks arise from our need for definitions, boundaries, and tangibility. A bit of mystery characterizes every romance – it’s what makes the chase so thrilling and the other person so intriguing. Yet there comes a time when the mystery gets old. The unknown is unnerving, particularly when it comes to emotions (where we’re the most vulnerable). With our hearts on the line, we need to know where we stand in the other’s eyes. And the only way to achieve that is to put ourselves out there and ask the inevitable, “So what are we doing with each other?”

But whether we’re the initiators or the avoiders of those conversations, we need to first determine if we’re ready for such demarcation. As a generation, we don’t like to waste our time. Our lives must be planned out as soon as we graduate, that new job must put us on the fast track to our dream career, and any significant other must be worthy of the long term or we don’t date at all. We don’t gamble our futures, so the pressure to solidify or deny the uncertain really puts us in a corner when it comes to our emotional well-being.

There are those whose need for structure takes over, and they rush into romantic situations for which they’re not prepared. We all know someone who has been blindsided into the girlfriend status (or perhaps someone who has done the blindsiding). And any pairings that arise from those instances are doomed to fail.

Then there are those like me, who will deny until their dying day all romantic entanglements. It’s the flip side of our generation’s intolerance for ambiguity—a fear-of rather than a compulsion-for definition. If all that matters is emotions, why do we need to pin them down when we’re sure of what we feel? Unfortunately deliberate ignorance is also an equation for catastrophe. Resolving nothing, it only pushes aside those pesky matters of the heart until they rear their messy heads again.

Though uncomfortable to the max, “define the relationship” talks are crucial to developing healthy romantic interactions. We’re not the only ones whose hearts are at stake, and we can’t forget about the other person’s feelings in our selfish quests for specificity or denial. But timing is everything here. Having these conversations too soon or too late in the courtship may spell disaster. Progress happens in due time. If your partner isn’t ready for a certain label, it doesn’t necessarily mean they’re ready to kick you to the curb. Relax and enjoy the courtship. Bode your time, take heed of your emotions, and most importantly, listen to your partner.

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It was Spring Semester of my freshman year at college and I was going on a date with Andrew, an older guy whom I’d met at a fraternity/sorority function. I waited anxiously in the lobby of my dorm, checking myself out in the mirror that lined the back wall, making sure that my hair was in place and my dress wasn’t on backwards. Andrew picked me up and we embarked on a magical evening of intimate glances over dinner, waves breaking on the sand, and a lingering goodnight kiss when he finally delivered me back to my door.

The night had been perfect except for one thing – that’s not how it really happened. In truth, while I did meet Andrew at the fraternity/sorority function, I had also made out with him that night, and while he did pick me up at my dorm, he was twenty minutes late. When I got in the car he said something about how “awesome” the other night had been, and while the dinner was delicious, the conversation was far from thought provoking and the kiss goodnight was more of a full-on attack of the tongue.

Needless to say, that was the last time I went on a date with Andrew. What surprises me is that in all four years of college that was the last time I went on an actual date, period.

That’s not to say I didn’t have my fair share of flirty fun. Guys bought me drinks, but it wasn’t over dinner; I was taken on weekend getaways, but it was with twenty other “couples” and our “chariot” was a yellow school bus; guys asked me to dance at the local bars, but as a form of foreplay, setting the stage to boogie down between the sheets later that night. Looking back, courtship in college was well, a sinking vessel. In the world of dorm rooms, dining halls, TAs, and “Thirsty Thursdays,” has traditional romance fallen off the radar?

Maybe our antennae are simply tuned to a different channel. The idea of going to college with husband hunting on the brain is about as passé as the Partridges. The courtship rituals of our parents’ youths have evolved past recognition, so consider college as your chance to learn the new rules. It’s true that handwritten letters have been replaced by text messaging, and it’s likely that all stages of any relationships will be broadcast on Facebook. With love in a whole new ballpark, it’s no surprise that graduating unwed, unengaged, and even unattached, is the norm.

Now cynics, postpone your victory party – romance is not dead. Rather, the four years that were once used to find your husband are now the four years used to find yourself.  So don’t waste your time being disappointed that Prince Charming hasn’t ridden his white horse into your cafeteria hall. He’s out there somewhere but, for the time being, he’s probably boozing it up with his frat brothers, which gives you plenty of time to live it up with your girlfriends until he’s slept off his massive four-year hangover called college.

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Ever had to turn down a date because you had to work or we’re just too tired after the daily grind at the office to muster up the energy for an evening out? For women of our generation, the drive to pursue a career often outweighs the importance of relationships. Our ability to be economically independent and dream-driven is a hard won necessity, but in the US, where we work more than any other industrialized country, new issues are arising. Career women are staying single longer, marrying later, and divorcing more.  In our generation, is loneliness the price of success?

The Sex and the City film and series candidly depicts this cultural conundrum as it chronicles the lives of four single gals in New York, and the romantic dilemmas they face as career women in post-sexual revolution America.  While the HBO show exaggerated female promiscuity, it did accurately portray the fact that successful workingwomen are, in reality, marrying later.

In the Australian book Man Drought and Other Social Issues of the New Century, Bernard Salt asserts “the average age of marriage for women (has risen) from 21 in 1971 to 29 today.” But what’s unique about our generation’s career women is that we are more likely than men to put achievement before romantic relationship.

In a Scientific Journal study entitled “Gender Issues,” researchers interviewed 237 undergraduates asking them “to rate the importance of goals such as financial success, career, education and contribution to society, as well as goals such as romantic relationships, marriage, children, and friendship.” They found that 61% of men prioritized romantic relationships above achievement, compared to only 51% of women.

This trend implies that in order for women to pursue their careers, they feel they have to do it alone. Perhaps it’s because relationships take an overwhelming amount of time, and, if put before your grades, a looming project, or long hours, can result in lower performance level.  It’s simply easier to focus when you don’t have to be responsible to someone else.

The issue of childbearing also forces many women to establish their careers in their twenties, holding off having a child until their early 30s. Putting in the long hours required to climb the corporate ladder is much easier without having to take care of a child at the same time.  Not to mention that, should a woman choose to start a family, she may need to take a leave of absence from her job, which can be detrimental in many competitive careers.

It’s hard for women to find men who value our careers as much as their own. In the Forbes article, “Careers and Marriage,” Michael Noer suggests that if men want a happy marriage they shouldn’t marry a career woman. He points to studies that state that we’re more likely to get divorced and be unhappy if we have children – not exactly the kind thing a lady would want a man to read before a night of speed dating.

The phenomenon Noer speaks of is directly related to the fact that men’s gender ideology has yet to catch up with women’s shifting role in society, according to UC Berkeley professor Arlie Hoschild. In her study The Second Shift, she found that ideology surrounding gender roles tends to make or break modern relationships.  If the man has egalitarian views toward women, he tends to value her career as much as his own and will help out with the “second shift” of housework and child rearing. If the man, has traditional gender views, he expects the woman to make sacrifices in her career to shoulder the entire “second shift.” She found that this caused bitterness and resentment in relationships, sometimes resulting in divorce.

So ladies, it appears we can take some advice from Carrie Bradshaw, and invest in good girlfriends and sexy shoes, as most likely the path to our careers will be paved by single-dom. In the meantime, establish yourself and your career; enjoy dating and discovering the values that you desire in a partner. And someday, when the timing is right, you just might find a man who shares your ideas of success and ultimate fabulousness, whatever those may be.

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