I just returned from a walk through the Provencal vineyards. I started the walk following a wide and well-trodden gravel path. Soon enough, I was venturing down the various small dirt roads that veered off course. I have all the time in the world, I thought. Why not? Some of the dirt roads were too uninviting to explore in full. Some led to dead ends. But some opened up to lavender fields, to quaint stone houses, to a river, or back to the main pathway. After the exploration, I returned to the hotel buzzing with a fuller appreciation of the village’s landscape.

Soooo with that, let’s talk about Dating, shall we?

A few days ago, I ended a relationship. The guy, for various reasons, was not of the typical mold of past boyfriends. “Off path”, if you will. But I was sufficiently intrigued by him, so we dated. It was a good few months — easy, enjoyable, drama-free. Circumstances were not right for a longer relationship, though, so it ended as quickly and as smoothly as it began. We talked, we agreed to disagree, and we parted as friends.

The absence of complications in this relationship was in stark contrast to my early dating years. All through my late-30s, my romantic story was a rom-com-horror show running on repeat: ditching perfectly good relationships and grasping on to bad ones; neglecting the good guys in favor of the bad boys.

To be fair, the pressure to find our Forevers before impending ovary failure would throw anyone into neuroses. Dating becomes akin to finding love in a factory. Our ability to discern becomes questionable at best. We force ourselves to decide on potential partners within a few hours of meeting based on their perceived capacity to charm us, make us laugh, hold clever conversations, keep their fingernails clean, make cute babies, and pay for said babies’ college tuition. If things (surprisingly) go past the first few dates, we clamp down on any wiggle room to turn back. We end up staying in unhappy relationships longer than necessary just to avoid starting the maniacal process over.

The two best decisions I’ve ever made occurred at the same time: I decided to turn 40, and to step off this insane train. I released myself from the pressure of marriage and children — rather than Must haves, they became Nice to haves. And immediately, the heavens parted, angels carried the weight off my shoulders, and the dating world transformed for me.

Dating became so much more joyful. And sane! When the objective of each date ceases to be To Find The One, we can fearlessly explore, wander off path on new dirt roads, and frolic for as long or as short as we want. That is the gift of Midlife dating — it becomes a series of mini-adventures to relish.

To be clear, when I speak of midlife relationships, I am not talking of the stuff of quick flings.  These relationships can be every bit as sincere, meaningful and enriching as any other. First, because marital union is not the foremost goal, people are together because they enjoy each other’s company. Period. Off-spring potential and tax implications do not enter the equation. As such, there is an inherent acceptance and respect of partners as they are. Rarely are there judgements (“can I live with THAT for the rest of my life???”) or attempts to change each other.  Rather, each person is afforded the freedom to fully be themselves.

Because midlife dating allows us the space to explore atypical unions, it can also help shift our patterns and open us up to new perspectives. It expands our concepts of love and relationships. They expose us to different types of love and help us determine what works and what doesn’t work for us. More importantly, they expand our understanding of ourselves. Believe me when I say, being intimate with someone very different from us has the power to change us profoundly.

Finally, when we stop relying on any one person to make us happy, we learn to take care of ourselves. We learn to guard our happiness fiercely, and entrust it only to the worthy. If a particular route threatens our happiness, we need the courage to turn around. Happiness becomes the key criteria in our choices — including whether or not to be in a relationship at any given moment. When we decide to be in one, we can bring into it our whole selves.

By embracing the gift of midlife and the options that come with it, we fearlessly venture further afield with open hearts, armed with the knowledge that we can respond with a certain maturity and level-headedness that midlife brings. And while venturing out without the pressure of Finding Forever, perhaps we will gracefully stumble upon it.

Or, we may find ourselves exploring for longer than expected. And I promise you with all my heart that that route is equally as lovely, like a stroll in Provence.

I’d love love love to hear your thoughts.  Please comment in the section below.

Chiang Mai, Thailand.  Alone.

“What does a public tuktuk look like? I mean, as opposed to one belonging to a family? Do they have medallion numbers? . . .
And how do I know if one is available? Are they lit? Can I hail one from anywhere or should I go to a tuktuk stop? . . .
How do I pronounce that road again? Ra-cha-dam-no-en?”

I’m obviously in a state of mild panic. The concierge half-smiles in disorientation. I shake my head as a signal to ignore me, and I head out.

This is my first solo trip in Asia. Thailand is a friendly neighboring country, yet being here seems more daunting than the time I was left stranded alone in the middle of Nowhere, Tuscany or the time I was cooped up with 3 strangers in a night train cabin in France. At the back of the (easily recognizable and hail-able) tuktuk, I pondered why this was.

I arrived at the theory that it was because for the very first time, in this trip, I look like a local! Traveling around Europe or Latin America, for example, it was readily apparent that I was an outsider. Locals, then, would be more inclined to help or would be more forgiving of any faux pas. Looking like one of them, though, burdens me with an assumption that I can speak the language, am familiar with their customs, and know how to hail a tuktuk. And if I didn’t (because I don’t), there was a higher chance of not being assisted, or of being misunderstood!

The rumination continued: could this penchant for being an “other” extend to my life as a whole? Is this why I gravitate to places where I don’t fully belong — so there are lower expectations of me? Am I, then, just an unambitious coward?

Solo Travel as Philosophy

I don’t have answers to this far-too-early-in-the-morning cogitation. That was just an anti-climactic demonstration of where my mind wanders when I travel solo. And crazily enough, it is incidents like these that fuel my solitary travel habit despite being called “unorthodox”, “weird”, or “insane” (mostly by my very own mother).

Traveling unaccompanied offers experiences that don’t normally occur in a group setting — the aggravating decision to venture out or stay in, the pitying looks, the fulfilling conversations with strangers. During these experiences, we are also able us to listen to the ripples of thought and emotion that normally go unnoticed in the presence of company — nostalgia, anxiety, excitement, curiosity, fear. These ripples, while sometimes annoyingly circuitous (aka, this morning), can also be profound. These arising thoughts present clues to who we truly are.

In a sense, solo travel is an exercise in philosophy — the pursuit of wisdom to live a good life. According to Socrates, at the core of all philosophical tenets is the knowledge of self. When we have an accurate sense of who we are, we have the ability to make better decisions based on truth.

As collective species, we, unfortunately, are not very good at knowing ourselves — what we want, what makes us tick. We latch on to societal models hoping they will bring us happiness — get a good education, work hard, earn well, marry better, have children, save for retirement. These suggested models may not suit us, but we follow simply because it is what is done. Then we realize much further down the road that our lives have turned out to be very different from what we wanted them to be.

The more ambiguous we are about ourselves, the easier it is to be influenced by others. But the deeper we know what we want and where we’re going, the less threatening societal formulas can be. Our inherent truths, then, can (and should) be our compass for our decisions and actions. This is at the heart of a well-lived and happy life.

As such, the Roman philosopher, Seneca, urges the constant pursuit of self-discovery.

“. . . Examine yourself; scrutinize and observe yourself in diverse ways. . . [Philosophy] moulds and constructs the soul; it orders our life, guides our conduct, shows us what we should do and what we should leave undone; it sits at the helm and directs our course as we waver amid uncertainties.”

Caution: May Cause Happiness

While there are countless ways to gain self-knowledge, solo travel, I believe, is one of the most potent avenues. It rouses latent aspects of ourselves, introduces us to resonating perspectives, and teases out obsolete self-concepts. If we pay attention to our true inclinations, i.e., uninfluenced by others, and take the time to understand what they reveal, we go home from our journeys having made an even more valuable inner journey. These could lead to profound changes in our lives, which after all, should be the point of all this.

It was in one of these trips that I realized how valuable freedom was for me. This eventually led to my career shift. It was also in another where I realized what “enough” was for me. This eventually led to my lifestyle change. I don’t know what or where my rumination in Thailand will take me, but if history is any indicator, it most certainly will be another step towards a life more authentically lived.

Would love to hear your thoughts.  Please feel free to comment below.

London
“New York will always be here, and [will] never care,” a friend texted.

Another friend, in a separate conversation, intimated, “When you leave New York, the void left will instantly be filled by endless other New York incidentals — MTA delays, work frustrations, other friends . . .”

After silently recalling that quote about not needing enemies when you’ve got friends like these, I thought about the Buddhist lesson in non-attachment these guys were inadvertently imparting:  you’ll miss out on the promise of what is in front of you if you don’t learn to let go.  New York knows this all too well.  Things slide off New York like teflon. Fiery arguments provoked in the subway are shaken off a minute later with a shrug of the shoulders. Extraordinary dates kindled each night fade off under no-follow-throughs. Transformative conversations transpire and vanish between strangers who will never see each other again. New York is bu.sy.  It keeps moving. It doesn’t dwell, doesn’t cling. What is important, though, is when it is there, it is there.

As I took a bite (literally and figuratively) out of everything the city offered, New York was there with me. The romance between us was intense.  It educated me, then it partied with me until I had no more party left to give. It extricated preconceived biases out of me. It stoked my corporate ambition then drained me of all of it. It bombarded me with creative inspiration, and assaulted me with new aesthetic sensibilities. It beat organized religion out of me and crammed in place a solid home-spun spirituality. It wrung out of me love and hurt I never knew I had. It squeezed independence out of me, and pounded me with solid support. And it etched out for me the finest group of friends one can only dream of. New York put this very sheltered island-girl through its furnace and spat out something unrecognizable 15 years later. Then yesterday, as I was made to realize, it gave her a good-bye squeeze and turned right back around to dealing with its endless New York incidentals.  Youch.

So fine, New York.  It’s a deal. You go back to relishing the best blue skies on the planet, the bushy-tailed newcomers, and your majestic efficiency. I’ll concentrate on my current incidentals and feel the feels of this upcoming adventure. No jealousy.  And when I return, we can continue this insane love affair.

Meanwhile, feel free to drunk text once in a while. I really won’t mind.

Vienna, Austria.  I’m craving a good conversation, and I’ve got New York on my mind. The Viennese, I’ve come to realize, don’t do chats. Viennese conversations with strangers, while perfectly polite, are purely transactional. Ask one question, you get one answer.  (In fact, Viennese conversations with foreign-looking strangers don’t even reach the transactional level.  A woman at the grocery store ran away from me today.  But that’s another story. . .)

New York chats, on the other hand, are anything but aseptic. Ready or not, New Yorkers will weave their personal lives into the most impersonal of topics. Do what you wish out of this unrestrained (often TMI) openness. A recent overheard conversation captures it all:

Waitress: It’s better to drink tepid water.
Customer: What’s tepid?
Waitress: Lukewarm, like i how I feel about my husband.

Ah, New York. So special. 🙂 New Yorkers are open books with anybody willing to listen. Accustomed to being ‘polite’ and respectful of other people’s personal space, most outsiders would cringe at this overexposure. In most parts of the world, the norm for ‘proper’ conversation, particularly with strangers, remains within the boundaries of the “safe topics” — the weather, where we went, what we did. Consequently, interactions are sterile and forgettable. I would add that when dialogue is limited to how great things are going and what achievements we’ve accomplished, the result is boredom. Alain de Botton, in his School of Life series, says that for meaningful conversations to occur, one should have the courage to go beyond the facts, and venture into the uncomfortable territory of feelings, vulnerabilities and failures.

Maybe it’s the small living spaces that force New Yorkers to make a living room (or therapist office) out of the entire city, or maybe it’s a certain loneliness that makes us seek connections. But New Yorkers frequently and willingly dive headfirst into this uncomfortable territory de Botton speaks of.  A woman in my morning commute asked for a tylenol and regaled me with stories of the ex-boyfriend she had met up with the previous night; another woman crossed a crowded subway car to ask for my stylist’s contact details and told me about the fight she had with hers; the cashier at the grocery store recounted the emergency call she got from her son’s school about her son’s antics.

Of course, this rawness does not always lead to pleasant encounters (such as getting kicked out of cabs, or unwanted advances). But if we do not instantly reject these encounters, and instead, remain open to them and what they can offer, this lack of censorship can forge profound connections, even for a tiny moment. Contrary to what we’ve been taught about “polite conversations”, de Botton proffers that people actually appreciate being shown others’ failures and vulnerabilities. This has less to do about wanting to see others fail, and more about wanting to know that we are not alone in our struggles. Knowing “that our own sorrows have echoes in the lives of others” is what connects us.

After a particularly difficult breakup, I took a lunch breather at one of the benches in Rockefeller. A middle-aged man in shorts and sneakers, with elegant salt and pepper hair, sat next to me. After some silence, he casually mentioned he used to work in the area but quit the law profession to try his hand at entrepreneurship. We got to conversing; I prodded a little more about his life. He mentioned his wife had divorced him.  He went through a tough period, he recalled, but is in a much much better place. He then said, “Look it all boils down to this: we all just have to relax. Life has a way of working out.”

If we find the courage to bring our conversations to new depths, we may be pleasantly surprised.  Even in a large, impersonal city such as New York, we are offered countless opportunities to discover that at the other end of the dialogue is a person with the same struggles as we do — of finding an apartment, of finding love, of finding solace, of making it here. Through these meaningful conversations readily available at any corner grocery or park bench, the city becomes our surrogate family. It consoles us, uplifts us, encourages us, makes us feel less alone, and effectively makes itself enormously difficult to leave.

I would love love love to hear your thoughts.  Drop me a line in the comment section below. 

I made my first solid step out of NY this morning; I told my landlord I was breaking my lease. So today, I walked around the city feeling quite unmoored. What if I hate the cities I move to? What if I never find a good apartment again? What if? What if what if?

I entered the subway and took a seat. In front of me was a young man with a large sketch pad on his lap. He asked, “Can I draw you?”

I looked around, then looked back at him. He was looking at me. I shrugged, “Sure.”

We chatted a tiny bit as he drew. I told him I was from the Philippines but had been in NY for a long time. He said he had been drawing for a long time. The train crossed the Manhattan Bridge. He asked, “Do you want me to draw the view behind you?”

“No,” I said.

I watched as he proceeded to draw the view behind me — the Brooklyn Bridge, Chinatown. “I drew it anyway,” he said.

“That makes a nice going away present then,” I said. He didn’t ask me what that meant.

He then turned to complete the lower part of my portrait, hand rapidly sketching out my hair, my shoulders, and stuff around my shoulders. “I gave you wings,” he said.

“Wings??” I asked, hair on my arms standing. (Some of you may know that wings hold a special meaning for me, hence the name of this blog).

“You know, like Victoria Secret model wings,” he said defensively. He paused. Then continued, “But the message really is: Be Fearless.”

I smiled, and threw a side-wink of thanks up to the universe.