In the Playoff Games of Love, I’m totally Billy Cundiff

It was a 32 yard field goal for love and I missed.

Sometimes, I feel like an a-hole. Like a few weeks ago on that first date. Enter seasonal sports analogy: Team Kathleen was in the playoff game for love and I was the team’s equivalent of Billy Cundiff. That’s right, I was the kicker who only had 32 yards to a game-winning field goal but MISSED. Yea, this was the date that was going to put me in the SuperLoveBowl and I had just kicked wide and had to go home without getting to play for the “championship” ring.

There’s nothing more disappointing than sitting across from someone you think could be “it” and feeling like you’re just not on your A-game. It turns into an almost outer-body experience where you get to watch yourself plummet faster and faster, but can’t seem to come to your own rescue.  My heart kept bouncing back and forth between my stomach and my throat – had it been only a flutter, I might have been able to get it under control and build myself a life raft. Instead, I found myself head under water, drowning in flatly-told stories and saying “all-the-wrong-things.”

Somewhere between the sandwich and the dessert menu, I sighed with the thought that “this just isn’t going to amount to anything.”

The walk to my next destination might as well have been a walk along the green mile.

The farewell walk might as well have been a walk along the green mile. He had been thoughtful enough to accompany me to my next destination, but I almost wished he had shown less chivalry. Mediocrity is exhausting, and I was plum worn out from three hours being a mediocre date.  I needed to walk briskly, add a few extra blocks to my trek and let the winter air numb an already aching heart.

The good-bye was awkward enough that, if I tried really hard, I could find a glimmer of hope that not all was lost. But I knew better. As I made my way home later that evening, I resigned to what would become the reality – he would evaporate as quickly as he had appeared.

Love really is a game. Luckily, I’ve been an athlete my whole life, and if there’s one thing I’ve learned on the sports field that’s also applicable to the quest for love it’s this: there’s always another season to be played, which means there’s always another chance for victory… that is, as long as you’re not too quick to throw in the towel.

The Hazards of Online Dating In a Suburban City

Am I the Samantha Jones of suburbia? No... not exactly... but I do love a good cosmo.

“Does this mean you’re officially the Samantha Jones of Westchester?”

If only she was referring to that time a Vanity Fair editor told me I was a young Kim Cattrall!

Instead, that was my best friend’s response to an email — the exclamation point to a series of stories — referencing an awkward encounter in an elevator with an artist my gallery recently decided to represent.

“That would imply I’ve slept with every unmarried man in suburbia,” I replied. “I haven’t slept with them — I’ve just met them on OkCupid.”

Donnie’s email was the last in a string of run-ins with local guys the world of WWW dating suggested I fall in love with. When I had been matched with a good-looking artist who recently moved into the neighborhood, I was obviously tickled pink. Even better, he happened to be a sculptor and I happened to be coordinating a sculpture exhibition. The opportunity to meddle in both business and pleasure could not be missed, and so I sent an introductory email — a rare act of self-pimping.

Immediately upon hitting send, I forgot I’d ever read his profile.

And then, this week, my guest curator announced the addition of a new artist to the roster for our summer exhibition. A meeting and tour of our space was scheduled. The artist made his appearance.

“Gosh, he looks familiar!” I thought as I attempted the requisite pleasantries in the elevator (it’s so good to have you on board! The exhibition really needs your aesthetic… etc).

"Gosh! Why does he look like I'm about to steal his wallet?!" Yea, it was an awkward elevator moment

“Gosh! He looks like he’s afraid I might steal his wallet.”

The next day — the email came with all the answers.

“I recognized you from OkCupid. Sorry, I saw your message but I’m seeing someone. I’d be happy to go for a hike or meet for coffee as friends some time.”

As uncomfortable as it was reading that email in the office, my real-life encounter with Donnie was the least awkward of all similar encounters. Sean was the nice real estate agent I eventually began exchanging text messages with. We found each other during my job’s peak season and I was frequently cancelling our scheduled rendez-vous. Eventually, the inevitable happened — we met standing in line at Starbucks. He was less than cordial.

Thanks to online dating, I can no longer buy coffee from the Starbucks across the street from my office, go to the movie theater a block away or order tostones from the Puetro Rican restaurant around the corner. All of these places are frequented by the men I’ve either asked out, been asked out by or been on a date with. Westchester is not a small county, but the number of single men under the age of 40… well, that is a relatively small number, and apparently, they all know my name.

“I guess it’s better to be the Samantha Jones of suburbia than a Desperate Housewife.”

Only a best friend could say something like that and live to order another cup of coffee.

I guess when it comes to suburban dating, it's better to be a Samantha Jones than a Desperate Housewife... for now...

We Had Dinner. We Kissed. Now What?

It wasn’t just a random hook-up. They had met through a Friend. Spoken on the phone. Gathered for dinner. Caught a movie. And made out in the parking lot like a couple of wayward teenagers.

He told her she was amazing. They agreed it had been a fun night and stared into each other’s eyes with clear intent. She turned to make her far-too-early departure, but not before he planted one more kiss and said:

"Soon" is non-specific. How soon is soon? 72 hours later or 5 months later?

“Let’s get together again soon.”

Recounting the date over brunch with her girlfriends, this was the phrase that raised all our eyebrows, hers included. “Soon” is non-specific, and we all tacitly confessed to having done it before — met someone (an old friend, a new friend, a recent date) and said “let’s get together soon,” with plans to avoid a follow-up.

Over the course of the last year, I’ve run the full gamut of date follow-up possibilities – from the guy who calls tomorrow because he can’t wait to see me again to the guy who stays in touch, but waits 5 months before suggesting a second rendez-vous.

Both blooming relationships faded away. But I’ll confess, the boy who sent me the “So rarely does a woman meet my expectations, let alone exceed them…You’re wonderful… are you free next weekend?” was the boy more likely to win my heart than the one who took 20 weeks after our first kiss to ask me to dinner.

More often than not, we walk away from a first date with a certain ambivalence. We had a nice time, but we’ve yet to make a decision about what’s next. He had a great sense of humor, but can he be serious? He had nice eyes, but do you really want to take his shirt off?

When it's more than a kiss, it's more than an stamp of approval -- it's a slobbery promise.

Sometimes, to help us make a decision, we need a nudge. A kiss at the end of a night is supposed to be a good sign — things went well, the attraction is mutual, here’s a stamp of approval. When it’s more than a kiss, it’s more than a stamp of approval. It’s a kind of slobbery promise that there will be a next time.

But more than a kiss followed by a “let’s get together again soon” or “…one of these days” and well, the scale hasn’t been tipped in favor of a round 2.

When you’re out there playing the game for love rather than lust, both sexes need to take some Jane Austen advice to heart: “In nine cases out of 10, a woman had better show more affection than she feels… he may never more than like her, if she does not help him on.”

Frankly, a “soon” doesn’t help me on.

Next, please!

Odds that the Next Guy I date Will…

Have a tattooed sleeve: 1 in 2

David, did you borrow my lace top again? Oh wait, those are your tats!

From the chef with the butcher’s map of a pig tattooed from this wrist to elbow to the Frye Boots specialist with the Man Ray photograph etched into his left forearm, it seems every man I share a drink or afternoon with is a painted gentleman.

According to a survey published by the Pew Research Center in 2008, 4 in 10 Millennials (the young adults of the early 2000’s) sport tattoos. Within this group, more men have tattoos than women.

Sometimes, I find the tattooed sleeve disarming — what’s he doing wearing my Zara lace top? But on the whole, I don’t mind it. I guess it’s a good thing I’ve always found a lil ink to be very sexy.

Live with his mother: 1 in 4

The most recent census revealed that nearly 6 million Americans between the ages of 25 and 34 lived at their parents’ homes last year. I was one of them. But on the whole, young men are nearly twice as likely as women to live with their parents. Of the last 5 guys I’ve met in this age group, 3 have lived with their parents.

These days, if he lives with his mother, it's not a strike against... it all depends on when he decides to tell you

Statistics and personal experience show, if I’m dating in my age group, a romantic night in, cooking dinner for him at his place, might entail cooking dinner for his mother (and father? and sister?).

So, in 2011, is it a strike against if a guy lives with his parents? I guess it all depends on a number of factors. But in this day and age, if all other signs of adulthood are neatly intact, it’s hard to call him anything but sensible.

Have traveled outside the US: 1 in 3

For the 2008/9 academic year, 260,327 students studied abroad, according to the Open Doors Report on International Educational Exchange. With NYU as the leading sending school in the US, this means odds are pretty good that a Manhattanite has traveled and even spent a significant time outside his homeland.

Only 30% of Americans have a passport, but odds that my next date will have traveled abroad are still pretty good.

But what about non-NYC educated folks? Or what about the possibility of meeting someone who’s seen the world without the help of academic programs? The numbers suggest my next date will have at least a willingness to journey in a foreign land.

Of the 308 million-plus citizens in the United States, 30% have passports. Owning a passport, of course, doesn’t guarantee that it’s been put to use. CNN posted some interesting stats: There were 61.5 million trips outside the United States in 2009 and about 50% of those trips were to either Mexico or Canada.

And yes, Canada is a foreign country, eh.

Have a graduate degree: 1 in 9

On eharmony, you can limit your dating pool according to education. If it’s a priority that your mate have at least as many degrees as you, then check a box, and the logarithm will take care of the rest.

As of 2003, approximately 25% of all Americans could boast a bachelor’s degree or higher. In a region like the North East, odds of landing a date who’s graduated from college is probably closer to 1 in 2. But a graduate degree? Well that gets tougher.

Only 9% of Americans have a masters degree, but New York is not America.

Only 9% of Americans can say they have an MA or MS or MBA. But again, New York isn’t America. New York City has the most post-graduate life sciences degrees awarded annually in the United States while Columbia University alone currently has approximately 17,833 students enrolled in various graduate programs.

Looking at these regional statistics, along with the contemporary reality that an increasing number of people are turning to graduate school as an alternative to a sucky job market, it seems the odds of finding a guy with “at least my level of education” would be in my favor… eventually.

There's nothing classy about a Red Sox fan.

Be a Red Sox Fan: 0

The Red Sox nation has a surprisingly strong representation in New York. It’s uncomfortable, and I won’t deny, I have a terrible habit of falling for fans of my team’s arch-nemesis.

But the chances I’ll actually allow myself to date one? Not a shot in hell.

They Warned Me I’d Find Love, the Summer 2011 Edition

The mating rituals of Banana Slugs give new meaning to the term "cock-blocking"

The Ariolimax columbianus, more commonly known as the Banana Slug, is ubiquitous in the rainforests of the Pacific Northwest. The Banana Slug is a hermaphrodite. When mating time rolls around, Banana Slugs engage in an act called “penis jousting.” Somehow, the slugs fight until one slug’s penis gets knocked off. The winner gets to be “the man.” The loser has to carry the eggs.

“Banana Slug mating rituals sound a lot like a Friday night in a Manhattan bar,” I told my guide as we sloshed through the green squishy stuff that covers the floor of the rainforest on Meares Island, a small island off the coast of Vancouver Island, British Columbia.

Cock-blocking had suddenly taken on a new, more serious meaning.

My guide chuckled and, lost in the mental comparison I was drawing between slug life on Vancouver Island and the NYC dating scene, I slipped on a cedar plank.

Whoosh, slap, squish, thud <– Those are the sounds an eco-tourist makes as she falls in the forest.

There's a lot of green squooshy stuff in the rainforest. Where's my mountain man to help me up when I fall?

Down the trail, a fiance hoisted his fallen fiancee back to her feet —  another victim of the squooshy green stuff — while I flopped around, clumsily trying to make it onto all fours without eating anymore lichen in the process.

Where was my mountain man in shining plaid when I needed him?

A few days earlier, I arrived in the great Canadian City of Vancouver ready for 10 days in the woods, away from work, domestic duties, and dating in the city. Or so I thought.

As soon as my rental car drove across Vancouver’s city limits, my phone started beeping relentlessly. The little blue light that illuminates whenever I have an OkCupid message was flashing like a lighthouse beacon in a hurricane. When they warned me I’d find love on this Canadian adventure, they weren’t kidding.

Hello, Mr. Vancouver. I knew I had a lot to look forward to on this vacation...

Warning! New matches ahead! Warning! New messages!

I opened the alerts icon in disbelief. I had been in Vancouver not more than 30 minutes, and already my inbox was overflowing.  There were notable similarities between the Vancouver men and the Brooklyn men OKCupid frequently found for me (why are they always in Brooklyn?!) — beards and plaid, in all their incarnations, were the standard uniform and a commitment to “sustainable living” was high on lists of interest. That’s where the similarities ended.

Good-bye hipster. Hello mountain man.

Good-bye bike-riding, semi-unemployed, struggling artist. Hello banker-turned-kayak-instructor who plays in two hockey leagues, sails on weekend and skis in the winter.

I knew I had a lot to look forward to on this vacation. And apparently, it wasn’t just the sea-kayaking.

The Online Dating Match Approval Matrix: Or, a Road Map to Choosing Mr. (Almost) Right Online

Online dating is a challenge. As websites bombard you with supposedly viable matches and your inbox fills with messages and winks from men who think you’re “a cutie” or “reeeeeally cool,”  you think: it would be nice if there was a road map to help me weed out the guys I could walk arm in arm with from the ones I may need a restraining order against.

After months of scanning, surveying, replying, blocking, and first-dating, here it is, to your rescue:

The Online Dating Match Approval Matrix.

(in the style of New York Magazine’s Approval Matrix)

The Online Dating Approval Matrix -- Your Guide to Finding Mr. (Almost) Right Online