Photo by Wettly via Flickr

Tell me if this sounds familiar. You’re at a party and find yourself talking to a friend’s friend. He seems really cool and makes you laugh, but honestly, you don’t find him all that attractive. Later, he asks if you want to hang out sometime. You agree… hesitantly. Then you make an excuse to leave before he can ask for your number.

Been there, done that? Then, like me, you’ve suffered from a type of romantic tunnel vision, where you lose all interest in hanging out with someone you don’t immediately see as romantic potential.

The problem with this behavior is that we need friends of the opposite sex. They help us see life from another perspective. That guy asking to hang out may be looking for something more, but he could just as well end up becoming a friend.

I go to my guy friends for their unbiased (or sometimes totally biased) opinions on everything from dating to whether I’m too fat to wear a bikini. Unlike the girls who will undoubtedly answer, “no you look great, really,” the guys will give me their honest opinions and often offer a fresh point of view.

It’s hard to explain the differences between relationships with your girl friends and relationships with your guy friends without getting into stereotypes. But it is a unique relationship I’ve learned to value as I’ve gotten older.

The most obvious example? When I need to know all the stats on the new Padres’ pitcher or an update of the Charger’s season, I get my guy friends to give me the Cliff notes version.

But more than just for sports, guy friends can be like cultural translators. Thanks to my brother’s friends for example, I can totally speak “geek.” I’ve never owned a comic book in my life, but thanks to the guys, I can compare Stan Lee characters, critique a Kevin Smith movie, recognize Vulcan references, and make quips about World of Warcraft. Don’t even get me started on Star Wars! This comes in fantastically handy, not just working in a preschool, but carrying on conversations with men of all ages.

If I want to enjoy a nice, quiet evening, sipping wine while chatting on a pristine white sofa, I can hang out with my girls. But it’s my guy friends who organize beer pong and flip cup games, where it’s perfectly acceptable to belch as loud as I can. Plus, with all the tall, muscular or beer-guzzling guys around, I can get away with being completely unfeminine and still feel cute and girly.

Also, for whatever reason, there’s a difference between your guy friend telling you how cute you are and one of your girls saying the same thing. There’s also a difference between hearing it from a boyfriend and hearing it from a platonic guy friend. Platonic love lets us know we are loved for who we are, completely separate from any sexual or romantic motivations. There’s just something more sincere about the compliment when it comes from a platonic guy friend.

Especially when you are dating and the romantic relationships in your life come and go, relationships with the opposite sex are comforting. It’s placating to know that I can still get my testosterone fix even without the boyfriend. I enjoy having someone who will “drag” me to UFC, so I can have an excuse to watch it and, admittedly, check out the other guys at the sports bar.

Guy friends can be your designated date when the occasion calls for it, preventing all those happy couples from patronizing you. Best of all, guys have other guy friends. Sometimes cute guy friends… the kind you just might want to date.

So try this: Before you blow another guy off at a party or a bar, let him know you’re not really looking to date him, but he’s really fun and interesting to talk to, and you’d love if he came to hang out with you and your friends sometime. Or just friend him on Facebook—whatever approach works for you.

You’ll be surprised how much fun you can have when you switch out of dating-and-mating mode and enjoy the friend zone.

But do the guy a favor and make sure he’s clear that he’s in the friend zone… especially if his eyes seem to linger a bit too long when he tells you how cute you are.

Photo by Marley Musella

One of my pet peeves is the single person who hates being partnerless. Hollywood loves to play up the stereotype of the woman who is desperate for anyone to love her. Sadly, a lot of my friends fit right into this cliché. They hate going to special occasions without a date on their arm. Or they complain about being the only unattached person on the planet, which is how life appears from their perspective.

So, I’d like to offer a different perspective. While I look forward to meaningful relationships in my future, I enjoy dating. Yes, someday I hope to find “the one.” But, in the meantime, I relish the chance to get wild on the dance floor and represent “all the single ladies.”

Here are a few reasons I love being single:

1. Social Currency

How often does anyone ask if there are going to be any nice married couples at the party? I’ve yet to hear it. Instead, my very presence as one of the cute single women (or at least one with a great personality, hopefully) increases the potential fun of any social gathering. Parties have a different energy when people have the possibility of meeting the man or women of their dreams… or at least finding someone cute to talk to or make out with later on. Simply being available increases our value as social currency.

2. Ogling Season

The entire season of summer seems designed with the single person in mind. Surfers out of their wetsuits. Guys jogging without their shirts, and girls in bikinis. Cute neighbors by the pool. Basically, it’s ogling season, and when we’re single, we can look and appreciate without anyone getting jealous.

3. Crushes

One of the fun things about being single is developing all of the little crushes. Just about everywhere I go, I have someone to look forward to seeing: the guy at work who impresses the kids with his dinosaur sketches, the cute guy on my soccer team who always compliments my defense, my friend’s friend who teases me at all the parties. The joy of crushes is that most of the time, we don’t even have any expectations of pursuing a relationship, but sometimes we’re delightfully surprised when one forms.

4. Friend time

We all swear we won’t dump our friends once we get involved in a relationship. Yet, the more we hang out with someone, the more our calendar fills up with activities with that person. Sometimes, we stop making our own plans altogether and just assume our weekends will be spent with our significant other. When we’re single again, that first weekend can be a wake-up call, as we realize we didn’t make any plans, and our friends no longer invite us out. So, we’re forced to pick up that phone and reconnect with our friends. We rediscover how fun quality friend time can be.

5. Productivity

Relationships often take a lot out of us emotionally. When I’m truly single, I get so much more done on all my projects. It’s as though all that brain space dedicated to dating, relationships, or breaking up is suddenly freed up for other interests. We have time to take those classes, write that book, or do whatever it is that became less of a priority when we were spending quality time with our guy or girl.

6. Self-reliance

When I asked a friend what he loved most about being single, he gave me a very succinct answer: self-reliance. When we’ve been in a relationship or even serial dating for awhile, we forget what it’s like being alone. We get used to doing a lot of the things we love or even those chores we loathe with someone else. Being on our own again means relearning that alone doesn’t have to mean lonely. Not only is it okay to watch movies all by ourselves, we can finally watch the ones we wanted to see, but which had always been voted out.

7. Endless possibilities

My favorite part of being single is the feeling that anything can happen at any moment. I love the idea that life is full of potential. Being in a serious relationship can be wonderful, but when we are with someone, the future can become somewhat limited. Where we’ll live, what type of job we’ll have, where and how often we’ll travel, how long we can get away each time—these are all serious considerations when we are involved with someone. Without the extra dimension of a significant other, much of the world opens up to us. We feel like we can go anywhere, do anything, and dream as wide as we wish.

Thus, I say that we enjoy this time to ourselves. Being single now doesn’t mean being lonely forever. So we should savor it.

Photo by HerLanieShip via Flickr

My friend has embarked on the noble journey of making himself into the “Perfect 10.” He figures that if he wants to date a woman he considers the ultimate match, he himself needs to be a perfect 10.

Everyone has their own idea of who their optimal mate is. My friend wants someone who is confident, sexual, financially-stable and many other remarkable and understandably desirable qualities. So, he is working on improving his own shortcomings in these areas.

I love the idea of self-improvement and becoming the best person you can be. There’s nothing like the self-confidence having a great job, a nice car, a fantastic body, stable finances and interesting hobbies gives you.

It’s a wonderful idea, reaching your full potential as a human being and meeting someone who meets all your requirements, who is simply right for you. But what happens when your exemplary partner loses his job or she gains 20 pounds? What happens when the stock or housing market crashes or that marathon runner has to have surgery on her knee? What happens when you have kids and can no longer afford or have time for all of those interesting hobbies?

I’ve had excellent jobs that left me with no time for anything else, but looked respectable on paper. I’ve reached my ideal weight and fit into my skinny jeans. I’ve traveled to amazing places. I’ve run a marathon in Athens, Greece. Yet, I’ve never felt like a perfect 10. I don’t know the woman who does.

One evening, at a time when I was at my skinniest, the guy I was dating was complimenting me on my small waist and chest. A year later, I’m wearing my fat jeans again and my chest has grown a few cup sizes. Would he still find me attractive now? I wonder.

Like my weight, all aspects of life fluctuate, which is why the part I love most about marriage vows is the promise to love and care for one another “for better or worse, for richer or poorer, in sickness and in health.”

The problem with falling in love with someone at their peak, when they are at their most perfect, is that there’s no guarantee you will still love them when they turn out to be merely human. Experts often cite finances and life changes like a new career as reasons for divorce. Another explanation for people being unhappy in marriages: reality sets in. No one can be at their best forever.

Conversely, someone falling in love with you at your peak, when you’ve finally gotten everything you’ve worked so hard for, makes you wonder if he or she would have loved and supported you through the tough times, as you struggled to become the person he or she admires.

I’m sure my friend will become the man he wants to be, his ideal self. He’ll find his perfect 10, and she’ll recognize him for being her optimal mate.

As for me, I’m looking for the guy who will fall for me when I’m at my fattest, when I’m struggling financially and stressed out about my job. The guy who will love me without make-up, in my over-sized sweats, with all my little insecurities. The guy who will see the beauty in me when I’ve forgotten it myself, when I’m feeling like a 5 on my own list—that’s my perfect person.

If someone can fall in love with you during the tough times, surely that person will be even more delighted to stick around for the good times. As Marilyn Monroe once said, “I’m selfish, impatient and a little insecure. I make mistakes, I am out of control and at times hard to handle. But if you can’t handle me at my worst, then you sure as hell don’t deserve me at my best.”

Image by PhotograTree via flickr

The scene is familiar: I’m at a party chatting with a group of friends. Gradually, we draw in the nearby group of guys, and before long, I’m amiably discussing quantum physics or artificial intelligence or some other topic I’m completely unqualified to have any opinion on (but do, anyways).

Then, the conversation turns personal: what do you do, where do you live, do you have roommates? I suddenly feel like a sea anemone with bright flowery tentacles, trying to ensnare the unsuspecting innocent guppy into my trap.

“Actually,” I reply, “I’m a full-time single mom.” Often the expression on the guy’s face reminds me of a black and white mushroom cloud rising up after the bomb has been dropped.

When the smoke clears, drinks need to be refilled, a buddy needs to be found, and my friends and I start swapping stories about how absolutely adorable my three-year-old is. Disaster averted.

Every once in awhile, though, some poor fool is too distracted by the décolleté and short length of my dress to run screaming in the opposite direction. He gets my phone number, and inevitably, the question becomes, “so how does this work, dating a single mom?”

Relax guys, it’s easier than you think. If you want to date a single mom, just ask her out like any other woman. If she likes you, she’ll find a babysitter. Trust me.

Of course, after the first date, it gets more complicated. It’s important to find a balance between fun during the day and romance at night.

Moms, especially full-time single moms, get this little thing called “mom guilt.” You aren’t going to find too many stay-at-home single moms. We don’t really have what other people consider “free time.” When we’re not working, our time is kid time (or chore time).

In the beginning, your job is to make sure that the woman’s time away from her kid is well-spent. That means participating in activities she can’t do with her kid: going to an R-rated movie, eating dinner in a fancy restaurant, or going out dancing. Or if it’s during the day: rock climbing, surfing, or snorkeling.

I once dated a guy who wanted to hang out and do all the stuff I usually do with my kid, but he didn’t want me to bring my kid, because he said it was too early in the relationship. So there I was, watching football games on TV, laughing at cartoons, and going on easy hikes, all things I love doing with my son. Instead of enjoying myself, I quickly found myself regretting wasting those memories on some guy I hadn’t even decided I wanted to keep around, instead of the most important boy in my life.

Of course, as the relationship progresses, and the woman finds herself spending more time with you, that means (if she’s a full-time mom) she’s going to start feeling guilty about all that time spent away from her kid.

Once you’ve passed security clearance, and she’s ensured you’re safe to bring around her kid, you can minimize the mom guilt and win major bonus points by inviting her and her kid(s) on an excursion that will be fun for everyone. The most fun dates I’ve been on were with a full-time dad, my kid and his kids. We went snorkeling and paddle boating, and watched movies under the stars.

Plus, this is where the real test comes in. No single mom is going to be serious about a man who can’t get along with her kids—or worse, can’t wait to get rid of the kid. I recently had a guy joke, “can’t we just tie him up for an hour?” Not funny. (OK, a little funny, but not helping the situation.)

The key to a mom’s heart is through her kid, but don’t try to fake it if you don’t feel it. We know a fraud when we see one. Adam Sandler’s movie, “Funny People,” illustrates this concept when his character fails to show emotion after his old flame shows him the video of her daughter singing a song from “Cats.” His lack of feelings is a deal breaker for her.

Think you’ve got all this down? You’ve impressed her. You’ve proven yourself with her kid. Now don’t forget to woo her. Just because kid time lasted all day doesn’t mean it should last into the night.

Discuss sleeping arrangements, find a babysitter, put a lock on your bedroom door, and spend some quality adult time. Let her know that while she’s somebody’s mom, she’s also an individual—a beautiful, sexy, smart, talented woman in her own right—then have some fun of your own.

Image by pareerica via flickr

For me, they usually come quietly, stealthily sneaking upon me when my thoughts are elsewhere.

The close proximity, the smiles, the steady eye contact, the pressing of knees in the bar, or a careless hand resting just a moment on my feet snuggled under a blanket. Jokes, dimples, and shared confidences. Whatever the cause, butterflies flutter in my stomach, and I’m thinking about a guy in a way I never have before.

What are these butterflies? Attraction, a crush, love?

Zack, for instance, made my stomach twist, flip, and want to shout for joy the moment we met. Unfortunately, he left on a ship, for five months, a few weeks later. Think it’s grueling waiting a week for the person you like to call you? Waiting five months to see what those feelings really were was torture.

These insects of attraction flit about, blind to what is healthy and careless of the past or future with an individual.

When Zack came back, I was ready for happily ever after, and he didn’t really care. He’d be out of touch for two weeks at a time, and I would swear never to talk to him again. Then he would call, and those butterflies would start fluttering, and my heart would start beating like crazy again.

I was in love with him, and I hated it.

So, when Max came along and I didn’t feel anything, I figured it was nice and safe. We dated on and off for a bit, but it wasn’t long before I realized I didn’t have much to hang on to without the butterflies.

Butterflies can be fickle. They come and go at the most unexpected times.

When I met Ryan, he was just another guy. We dated. We were friends. We talked about hooking up. We didn’t talk. We were friends. We talked about hooking up. We didn’t talk. We were friends….

Ryan was another Navy guy. When we met, I promised not to fall in love with him, being still in love with Zack and dating Max.

So, I was less than thrilled when a few months before Ryan was to leave for Guam (after he’d already expressed his feelings that he didn’t want to have any attachments to anyone), we were talking as friends one day and… flip, flutter, jump. Stupid butterflies in the stomach.

The really annoying part? When I wanted to know if the feelings were mutual, he said, “a blind man galloping by on a horse can tell we’re attracted to each other.”

Whether that stomach flipping feeling comes at first sight, months into dating, months after dating, or ten years into a friendship, it becomes the difference between merely answering his calls and obsessively counting the ticks of the clock between correspondences. They are the distinction between curiosity about his friends and jealously analyzing his relationship with all the girls who comment on his Facebook page.

Before the feelings, I don’t really care whether he thinks I’m too forward, too flaky, or slightly crazy. After the feelings, I despise myself for being absolutely out of my mind. Realizing this, I often try to hide it by going to the opposite extreme and avoiding giving him any sign that I’ve been thinking about him.

With those feelings, I hang on long after there’s nothing left to hang onto. For four months after I told Zack to never call me again, I was still trying to meet up with him on a monthly basis. Not a proud time in my life.

Yet in the absence of this quick heartbeat and nervous excitement, the silence of the heart feels too much like settling. After Zack, I was dating a guy, Peter, who was awesome and fun to hang out with, but when we kissed, I didn’t feel any spark. I liked him a lot, but it was difficult to know whether to keep dating him without the feelings.

Hoping the attraction would grow, I kept at it. But every time he disappointed me, I was ready to run. It made for an uneasy relationship. Without the tumbling nervous excitement that feels like butterflies flitting in my stomach, I don’t have a guide to know I’m in the right place.

I don’t think a romantic relationship can succeed without those butterflies, without feelings of excitement and quick heart beats. Yet, having feelings for a person is no guarantee there’s a chance for a romantic relationship either, even when the feelings are mutual.

Even more confusing, you never know when you these feelings might just pop up. Just because someone doesn’t make your palms sweat now or your stomach do cartwheels doesn’t mean he never will. Then again, enjoying someone’s company doesn’t guarantee you’ll ever feel that way about him either.

Art by mollycakes via flickr

Some women go through relationships like shoes; I go through men like jobs. I’ve had 29 jobs since I started working when I was 16. I’m not even going to try counting the guys I’ve had crushes on, dated, or hooked up with. My longest job lasted a year and a half, my longest relationship approximately four months.

These days it seems whenever I get together with my friends, they need a review: “Where are you working now? Which guy is this you’re dating?”

Breaking up with the last guy who found such shortcomings in my job insecurity has induced me to muse upon the connections between my work and my love life.

Every new job and every new relationship forces introspection. When people ask me what I do, I tell them the exact description of the jobs I’m currently working. Lately, those jobs have included special education aide, tutor, English as a Foreign Language teacher and grant writing consultant. So, I was struck when my new boss-to-be looked at my resume and observed that I’d been teaching six years. It was longer than I thought.

Maybe this is why I dislike statistics. I know some people find comfort in the rules of math, the seeming hard facts that digits provide, but like so many aspects of life I find this data a matter of perspective. I’ve had almost as many jobs as I’ve had years on this planet, which at first glance makes me think, “What’s wrong with me?”

A closer look, however, reveals that many of those jobs were simultaneous. In the 13 years I’ve been working, I’ve been unemployed a mere three months. Those are statistics I find soothing.

My love life is an equally nonsensical set of digits to manipulate. One guy I dated one month, but have been friends with for almost 10 years and acquainted with longer. In the last month, I began developing feelings for a guy I’ve known 15 months and dated only one time, 12 months ago. The only time I’ve been in love was with a guy I had known for only two weeks.

Dating statistics are often only a fraction of  the real relationship. Thus, numbers alone are insignificant, only the stories behind them bring meaning and understanding.

The seeming instability in hopping from job to job and guy to guy has taught me so much about who I am, how I love and the world at large. One of the patterns I’ve noticed about both is that first, I’m nervous and excited. As I get to know the new person or new position, I’m enthusiastic to learn everything I can and to succeed.

Gradually, I get more comfortable, fall into a routine and the shine starts to wear off. Sometimes the fantastic boss turns out not to be the amazing leader I deified in the beginning. Or the vast differences between me and the new guy don’t seem quite so complementary anymore. Employment and relationships end for so many reasons, but saying good-bye doesn’t get any better.

The hardest jobs to get over were the teaching positions in which I didn’t have a back-up plan, usually because I was so busy working and really didn’t want to leave. I often hope that somehow everything will work out for the best.

The most difficult lesson in life is the discovery that a job or relationship I thought was meant to be—because it seemed so perfect and to fit so well, I was certain it had to be ordained by the heavens—could crumble just as easily as that which I didn’t believe so deeply in. I’ve come to realize that I can’t rely on predestination or fate or some divine sign, but instead have to fight tooth and nail for everything I love and desire in this world.

I’ve learned to deal with the hard knocks of love and work life by adapting and trying to prepare for the eventual outcome. When the season, work year, numbers or money start to wane or end, the time comes to look for the next adventure. When the guy I am seeing becomes distant or undesirable, I keep my heart open for new opportunities.

With each new endeavor and romance, I must bend and adapt like branches of the willow tree, while my core continues to stand strong, confident that even without a distinct job or person by my side, I can survive any storm.

Photo by Brett Arthur via Flickr

Heads turned when this very Hot Guy walked into the Halloween party I attended this year. Dimples to the heavens, sparkling, mischievous eyes, and muscles a girl just can’t help but hang onto. Unfortunately, the illusion was quickly shattered by how obviously he wanted to get laid.

The first girl he struck up a conversation with hastily found a way out, groaning to us about how unattractive it is when a guy brings up sex within minutes of meeting. The rest of us concurred and didn’t bother conversing with him most of the night, though Hot Guy seemed to pervade the party.

Meanwhile two girls were in a flirting battle over the same “Nice” Guy, (who claimed to be single, but days later revealed that was just a part of his Halloween costume too), because he could actually hold his end of a conversation.

By the end of the night, Nice Guy was making out with one of the girls while two other girls were doing body shots off of Hot Guys’ very amazing abs. Apparently they had missed the incident of him ripping the police badge off a girl’s chest, getting slapped and throwing a drink at her.

Nice Guy went home with a girl’s number. Hot Guy got cockblocked by me, the designated driver, while he was trying to go home with one of the girls who had come later to the party and missed the drama. (The teacher in me was worried about the girl’s safety as he didn’t seem like the kind of guy who would take “no” for an answer and both he and the girl were pretty drunk. Being the only sober one, I would have felt responsible for anything bad happening.)

After she left, he wasn’t discouraged; he tried to convince the other girls in the van to keep his bed warm. He went home alone.

What a waste of that hot body. He was such a good-looking guy that if he’d had an ounce of tact, he could have had a lot of fun keeping his bed warm with any number of girls at that party, if not that night, then another one soon. I just felt like if I could have taken him by the hand and coached him through the party, I could have helped him get exactly what he wanted without him looking like such a chump. (Which I fully realize is ironic and hypocritical since I was the one who cockblocked him.)

Honesty is important, but if I were him, I would have toned down the desperation. Meeting a guy is, if not the goal for a single girl at a party, at least one of the excellent perks. When I meet single guys at a party or a bar, I’m subconsciously rating them on two scales: “Likelihood I’d want to date him” and “Likelihood I’d want to sleep with him.”

A really attractive guy doesn’t have to work that hard to stay on the high end of the “Likelihood I’d want to sleep with him” scale, even if he’s not even registering on the “Likelihood I’d want to date him” scale. However, one of the major factors that changes this is his ability to show discrimination.

I don’t want to sleep with a guy who will bang on every door in the city until he finds one that opens. Leading with sex is a turn off, because a girl wants to know a guy wants to sleep with her in particular, because he’s assessed her attributes and found them favorable, not merely because she’s breathing and there. I won’t qualify these attributes in anyway, because it fluctuates depending on what scale he’s on. I try to be fair, if I’m checking out his hot body, well, I’m not going to expect him to be interested in my personality.

I do think a guy should be honest about not wanting a relationship, but at a party where people are getting wasted and flirting sex is already on people’s minds, spelling it out at the beginning of a conversation isn’t necessary. If Hot Guy had spent more time chatting up different girls and then zoned in on one or two he was really interested in, he would have drastically increased his chances of sharing someone’s bed.

I know this, because I did kiss and give my phone number to a guy that night, not because he was incredibly irresistible, but because despite another girl totally flirting with him, he pursued me, just me. Sometimes that makes all the difference.

Photo by John Fraissinet via Flickr

When I broke up with the last guy I was dating, I tried to be polite about it. I told him he was nice, cute and fantastic—and he replied with a low blow about my “lack of stability.” Eww. He hurt my feelings, especially since I had tried to be amiable. I reacted by doing what I swore I would never do. I told him all the awful things I’d thought about him over the last month since it first occurred to me that maybe I didn’t want to date a guy who wore white shoes hiking and complained about them getting dirty.

I’m not usually such a bitch, but early on in our discussions, he’d said he didn’t see any point in staying in contact with the girls he dated once he’d broken up with them. So I felt I didn’t have anything to lose. If I’d thought we could be friends, I would have acted differently. Typically, I’m at least friendly, if not friends, with most of the people I’ve dated, a fact that he wasn’t very comfortable with. In his opinion, women are more likely to cheat with an ex because it doesn’t affect their “numbers.” In other words, sleeping with someone you’ve already slept with doesn’t change the number of people you’ve been involved with. I disagree. If I can’t trust the guy I’m dating with his ex, I can’t trust him with anyone. (And if I can’t trust him, I don’t date him.)

While during the relationship, I did find a sense of security in not having to compete with any ex-girlfriends, I realized the reason he didn’t stay in touch with his exes was that he wasn’t really friends with them in the first place. I want a friend as well as a boyfriend, someone who will always be a part of my life even if on the fringes, someone I can trust long after the romantic relationship has crumbled. This last guy I dated didn’t need to be friends with the girls he was dating, because he already had enough friends of both sexes in place to go out to dinner with and do fun activities with. The women he dated seemed simply necessary to take care of his other needs, but not to incorporate into his life, although this wasn’t immediately obvious to me.

Of course, I wouldn’t want to date a guy who was best friends with his ex either. One of my sisters dated a guy who still hung out with his ex-girlfriend, whom he had dated for several years. While the guy was dating my sister, the ex-girlfriend bought him a dog, baked him cakes, and the two of them went to lunch and dinner frequently. This became an area of major contention between him and my sister.

As relationships change, boundaries need to change too. I recently told one ex that if he wanted to continue being friends with me, he had to stop talking about my boobs. I don’t care if he talks about boobs in general, just not mine. Sometimes it takes time to adjust. I didn’t mind flirting with another ex with whom I’d had an amiable split, until I started dating someone else and he was still sending sex texts. He agreed to stop the flirting in favor of preserving our friendship.

On the other hand, just because we are now friends doesn’t mean I want to hear about the sex life of any guy I’ve dated, kissed, or even had a discussion about sleeping with, let alone actually slept with. I will genuinely be happy for him if he’s joyfully dating someone new, or commiserate with his dating failures.  However, when I had a guy I’d had feelings for tell me about the apartment-shaking sex he’d had with a one night stand, it just made me feel dirty and embarrassed.

In the future, I will consider a guy’s relationship with the previous women he’s dated more closely. If he can’t relegate his ex to the backseat, then maybe he’s not ready to move on yet. However, if people come and go too easily from his life, it’s likely that I will be in and out of his life just as quickly and with just as little impact. Ideally, the guy I date will have an amicable, but not inseparable, relationship with most of the people he’s dated. That way, even if the romantic relationship doesn’t work out, like Humphrey Bogart’s character at the end of Casablanca, I can look forward to “the beginning of a very beautiful friendship.”

Photo by Ed Yourdon via Flickr

I felt complete awe when one of my best friends in college, who’d had a distant crush on a law student we referred to as Tattoo Boy, actually went home with him one night after a random encounter in a bar. I was less thrilled when she told me how he’d said good-bye the next morning: “Call me. My number is in the phone book.” While my friend puzzled over whether he actually expected her to look up his number and call, I sat fuming in righteous indignation on behalf of women everywhere.

Although I personally never laid eyes on Tattoo Boy, he had a long-lasting impact on my life. My older more mature self would like to say that I learned to have respect for other people’s feelings. Unfortunately, that wasn’t the case at the time.

The first time a guy ever spent the night, I kicked him out so fast he barely had time to pull his shirt over his head. In my defense, during our brief few months of “friendship” he spent an equal amount of time flirting with my friend (who had a boyfriend at the time) and spent even more time locking lips with her. How do you tell a guy, “sorry, but I actually think you’re a jerk and not worth my time?” He called repeatedly over the next few days, saying what a good time he’d had, but I was too chicken to pick up and tell him the truth. Plus, he deserved it. Didn’t he? On some level, I felt I was reaping revenge on all the guys who never called some girl. That one was for Tattoo Boy.

I’m more than a little embarrassed to admit some of the ways I’ve broken up or blown off guys in my life.

I thought he was never going to call again

Having been advised by some guys that since I wasn’t a girlfriend, a guy wasn’t actually required to dump me, I was certain I’d gotten the heave-ho when I didn’t hear from the guy I was dating for two weeks. By the time he did call, I was already dating someone else, which was a shame since I’d really liked him.

Wrote a text message

Granted, the guy I broke up with via text message didn’t understand conversational English very well, but I admit it was still a wimpy way to break up with him. Especially since later when I saw his cute puppy dog eyes and mischievous grin in person, I immediately felt horrible and wanted him back again.

Before he’s fully dressed

Before I hooked up with my guy friend of almost a year, I was perfectly honest with him about not wanting a relationship, so when he asked me out to coffee later I refused. Unfortunately, that meant not only having that dejected look imprinted on my brain (right above that very lovely torso) for months to come, but having to see his miserable mug all over my very small town.

Left a message on his voicemail

So I finally got up the courage to tell a guy it was over and had everything I was going to say all planned out… when he didn’t answer his phone. Caught off guard, I recited the break-up speech anyways. Granted, he may have been the one who told me he prefers blondes—even though I’m a brunette. He may even have confided critically how his ex-girlfriend got too much “junk in her trunk” after they started dating, right after I had told him I’ve struggled with weight problems my entire life. Unfortunately, my voice calling it quits was the one captured on tape for him to replay over and over to all his friends. Who was the bitch then?

Got back together again a week, two weeks or a month later

Really, what had changed in two weeks? Did he suddenly turn liberal? Become less of a jerk? Was he more attractive? Did I suddenly expect him to start calling me on a regular basis this time? Did he somehow become more exciting? Did we now have more in common than we did two weeks ago? Seriously, how many times will I do this before I learn?

On the other hand, I secretly believe some of these guys have purposely chickened out and waited until I broke up with them. Honestly, we both knew it was over. He wasn’t calling me, we both would rather hang out with our friends, and we had nothing in common or nothing to say to each other. Yet, since high school I’ve almost always been the one to say we need to move on. (Both times I broke up with a guy.) Why?

It’s difficult to be honest with people, especially to their face or over the phone, but I should have learned years ago from Tattoo Boy that most people really don’t like that person who doesn’t have the courage to tell the truth or the finesse to tell it in a nice way. More importantly, I don’t like myself when I don’t show the respect for the other person by having the courage to break off any type of relationship in a way that preserves both people’s dignity.

Photo by Kit Haselden

As a kid, I used to watch the surfers riding the curls on the other side of the checkered flag with such envy; they made it seem so effortless. These days I look at my friends in long-term relationships with the same jealousy. Yet, ask a skilled surfer to teach you to surf or a blissful couple how to date, and their instructions tend to be vague and unhelpful. They started young and have been at it for so long, they don’t really think about what they are doing, they just do it.

Having started surfing in my early 20s and dating in my late 20s, I’ve really had to concentrate on the learning process of these two challenging activities. The processes of going from that first date to being in a bona fide relationship and going from catching that first wave to being recognized as a surfer have a lot in common.

Learning with Another Rookie

The first time I attempted surfing, my older brother borrowed his friend’s longboard, and we spent the day taking turns out on the waves. I watched him keel over, he watched me take multiple nose dives, and at the end of the day I wasn’t any closer to learning to surf than I had been at the beginning.

My first relationship attempt was similar.

My long-time guy friend made Steve Carell’s “40-year-old Virgin” look like Casanova. He loved the idea of dating another novice; it gave him a sense of security. Unfortunately, a month into it, I felt I needed more excitement in a relationship. I hadn’t learned yet that excitement isn’t exactly one of the key elements of a successful relationship. Communication is. At that early stage, neither of us communicated our desires, worries or goals very well. Although learning with another rookie wasn’t my style, I’ve witnessed it work for many others who cherish their first loves for the experience.

The More the Merrier?

When I finally bought my own board, I got so eager to learn, I’d try to catch every wave I could, no matter how weak or small, just to get the practice in. Sometimes, I’d exhaust myself attempting to surf a wave only to find myself standing up in six inches of water. Then, when the really good waves came along, I’d either be stuck with my fin in the sand, or my arms would be too tired from all the extraneous paddling to pop up. The more waves I rode, I justified, the better I’d get.

This “the-more-the-merrier” approach isn’t unlike one of my guy friend’s recent approach to dating. After what he explains has been years of being seen as a friend rather than a lover, he’s determined to gain confidence and raise his sexual appeal by dating and bedding as many women as possible. On a recent night at the club, he went home with four women’s phone numbers and followed up with every one of the women. Each experience, he says, boosts his social and sexual confidence, but I wonder:  Surfing the bubbling white foam of 100 waves after they’ve broken never prepared me for dropping in on a five-foot wave as it was breaking. So, if my friend’s goal is to have the confidence to win the heart of the woman he chooses, how well does jumping from one woman to another prepare him for a long-term relationship?

Waiting for the Perfect Wave

Some beginning surfers take the opposite approach to surfing. They paddle out past the breakers to where the experienced surfers lounge on their boards to wait for the perfect wave. They wait and wait and wait. Finally, when they sight that choice rise of water on the horizon, they turn their boards and begin to paddle. The wave lifts them. It’s now or never. The wave breaks. Whoosh! They find themselves under a four-foot wall of water flailing for the surface.

The first time I fell in love left me feeling just as helpless. Brainwashed by fairy tales to expect that when two people fall in love, they are bound to live happily ever after, I didn’t realize that patience wasn’t just required while waiting for “the one” to come along; it’s also a huge factor in developing a relationship. Since I’d never attempted to turn dating into something more meaningful, I didn’t know how to do it. If I’d had more practice with less at stake, I might have had more success.

Riding it out

One of the toughest lessons I’ve striven to master both surfing and dating is discernment. An essential step in improving wave-riding skills is deciphering which surges of water are worth the effort and which I should paddle over. As a beginner, I would start to paddle out on a wave, hesitate because it was too weak or big or slow or the timing was off.

When I look for reasons to fail, I find them. In my dating life, I was so busy trying to foresee whether I was “meant to be” with that particular guy, I never really gave the romance a chance. So, along with discovering that successful relationships take practice, patience and communication, I’ve also found that even when I’m not in a committed relationship I can still benefit by riding it out to see where it takes me.

The beauty and challenge of surfing is facing a new ocean every day. A new surf spot, a different tide, low winds or high winds, strong currents, flat water or giant curling beasts – each time I take out one of my boards, the experience is thrilling and novel. The same is true for dating and relationships, but the real phenomenon is that each time I’m bringing a new element and strength to the experience too.