Category: OKCupid


Embracing The Roller Coaster

October 10th, 2011 — 8:35pm

It’s often said that life is about the journey, not the destination. This weekend, I was reminded that the same can be said about dating – and that ups and downs are par for the (bumpy) course.

Saturday night, after two weeks of scheduling conflicts and phone tag, I finally met up with Connecticut-based bachelor M.

M chose the Beekman Hotel’s glorious Top of The Tower for our date, and made sure we were seated at an outdoor table with stunning city views. He was charming and sweet and the conversation for the most part flowed – except when he asked me one of my least favorite questions:

“What’s your experience been like on OkCupid?”

And so began a litany of his bad experiences, one which found me scratching my head for the umpteenth time over this line of small talk.

Why is it that so many guys want to discuss online dating? Isn’t the whole point of a first date to get to know each other, not compare notes about looking for love in cyberspace? If you met someone at a bar, would you devote 20 minutes to rating your best and worst pickup experiences there? Probably not, and yet for some unfathomable reason, this has been the rule rather than the exception with online bachelors.

That most unromantic line of conversation found me appreciating in a deeper way the more traditional communication I’ve been having with an old flame, Chris. After recently reconnecting (through Facebook, of course) for the first time in 14 years, Chris wrote me a beautiful letter describing what he hopes we might share now – and the places he wants to take me to his hometown. Inside the envelope, he also pressed a leaf as a symbol of the fall colors he’d love for us to take in together.

And just like that, I rediscovered that you never really know what can happen from one day to the next, be it a visit from your past or a new connection. It’s a roller coaster for sure. Here’s to learning again and again how to enjoy the ride.

| dating dos and don'ts, OKCupid, online dating, renewing old flames

Questioning How Many Times Cupid Comes Calling

September 14th, 2011 — 9:11pm

During a recent trip to the movies, I saw a trailer for the upcoming Anna Faris flick, “What’s Your Number?” The film’s premise got me thinking once again — do you get a limited number of chances for finding love?

Anna Faris muses about recycling exes in this EXCLUSIVE clip

Faris’ character begins to think so, after reading an article that says you’re out of luck if you’ve had 20 or more relationships. Of course, she’s hardly the first pop culture character to voice this anxiety. Remember that Sex And The City episode where Charlotte tells Carrie women only get two great loves?

By that standard, I’m in trouble. But even though I’m safely under the 20 threshhold (assuming, that is, that relationships of less than three months duration don’t count), I can’t help questioning the odds now that I’m closer to 40 than 30. Especially when I’ve already recycled the exes worth recycling, and the opportunities to connect seem fleeting at best, in a city where the dating equivalent of ADD runs rampant.

Recent cases in point, courtesy of OkCupid.com: a Connecticut-based bachelor who immediately gave me his number, proceeded to call me twice and then disappear; a fellow Upper East Sider who called and texted multiple times while out of town, suggested dinner upon his return, then also pulled a vanishing act.

Though these kinds of things are par for the course with online dating, I can’t help wondering if there is indeed an expiration date on getting to happily ever after. If you turn Cupid down enough times for one reason or another, does he eventually make like an ex-boyfriend and move on?

I’m guessing “What’s Your Number?” has an optimistic answer to that question. In the meantime, or on the above link for an exclusive and hilarious clip of Anna Faris talking about the merits of recycling past loves.

What’s your take on going back to an old flame?

| finding Mr. Right, OKCupid, online dating, Sex and The City

It Only Takes One

September 3rd, 2011 — 10:29pm

Someone once told me that, when it comes to most milestones in life — be it a job, a home or a relationship — it only takes one for everything to change. The combination of a good friend’s wedding and my return to online dating has reminded how true this is.

A few weeks ago, I met up for coffee with J, who got things off to an awkward start by saying–

“I don’t know how to greet you, since you’re a professional dater.”

It only went downhill from there, during an excruciating hour that found J quoting lines from bad movies and his fear of using in-flight restrooms for fear of where airport sewage goes. I felt uncomfortable and not myself the entire time, thinking as we parted ways what you usually do after a dreadful date…why do I even bother anymore?

Miraculously so, I managed to muster up the wherewithal a few days later to go out with another bachelor whom I’d connected with online. Much to my great surprise, we clicked. The conversation flowed and the evening ended with us holding hands and the promise of a second date. And just like that, I understood the reason I’m still putting myself through this unpredictable process, embracing the reminders of where it all will (hopefully) eventually lead.

I Do: Julie and Brian celebrate becoming husband and wife

Today was one of those reminders, as I witnessed my good friend Julie marry her beloved Brian. Julie and Brian met on OkCupid about a year ago, and they couldn’t be a more perfect match.

Like that wise person once said, it only takes one.

| getting married in your thirties, meeting Mr. Right, OKCupid, online dating

Embracing The Unexpected

August 24th, 2011 — 2:29pm

I recently corresponded with two women I met on last year’s US Dating Blitz — both of whom are engaged. As they shared their bliss during this pre-marital period, I couldn’t help thinking about how the unexpected is so much a part of wherever you are in the relationship spectrum.

For both betrothed gals, meeting their respective fiancés was a surprise. Cleveland native Jen joined Match on a lark, with what she describes as zero expectations. Atlanta resident Leah dragged herself to a holiday party she had no interest in attending.

Their respective happy outcomes reminded me you have to be open to wherever this process takes you. Case in point — my recent second date with a long ago colleague I connected with on OkCupid.

As I mentioned here, given our very rocky professional history, I can say he is the last person I would ever have expected to go out with.  And yet, we ended up sharing a great conversation and some laughs — a reminder that it’s always worth letting go of the past to make room for new possibilities in the present.

Congrats, Jen and Leah!

| meeting Mr. Right, OKCupid, online dating, The Great Dating Blitz

Skipping The Small Talk Online

August 21st, 2011 — 12:06pm

As I slowly come out of my recent dating hiatus, I’ve decided to give online dating world yet another shot. In just a few weeks of being active again on OkCupid, I am noticing an unfortunate trend – the absence of letting chemistry unfold (or not) organically.

More and more, it seems online bachelors are trying to divine within a matter of minutes whether you’re worthy of an offline conversation. At the age of 37, I can certainly appreciate not wanting to waste time. But that doesn’t mean I’m in favor of treating the process of getting to know someone like a bad job interview.

One guy asked for my relationship dealbreakers over the phone, explaining that it was better to find them out before we took the time to meet. Another one took his day job as an attorney a little too far, confusing an instant message chat with a cross examination.

After asking me how big my apartment is and whether I rent or own, he proceeded to list his requirements:

“Educated/professional/intelligent, feminine/girly, maybe a little arty, has sophisticated taste but not ‘alternative,’ physically i like fair skin, thin but not skinny, curvy but not fat, busty. Would you say you fit what I described?”

Call me old fashioned, but whatever happened to making normal small talk during an initial conversation? It’s like online dating has made people so jaded, they don’t want to trust that you can take a person’s profile at face value.

“What are you looking for on Okcupid?” Mr. Attorney persisted.

Already put off by his interrogation-style questions, I took another glance his profile.

As long as there is good music, cute girls and Coronas on hand I’m a happy camper,”  read his opening line.

Between that and his age range of 18-34, my verdict was that we were most definitely not looking for the same thing.

I’m looking forward to tomorrow’s date with Mr. Dealbreaker guy. His jumping ahead question came after 90 delightful minutes of small talk that didn’t involve square footage or mating requirements. If only there could be more of that in the online dating world.

| dating dos and don'ts, OKCupid, online dating

Reconsidering Who Makes The First Move

August 12th, 2011 — 1:05pm

When it comes to so-called dating rules, one of the most tried and true is waiting for the guy to make the first move.  I’m usually a big believer in this approach – though a recent conversation found me considering exceptions to it.

Over drinks at Midtown watering hole Sutton Place, galpal N shared her conundrum about the cute guy she encountered at a bar. The friend N was with could see she was smitten and opted to be bold for her, walking over to Mr. Cute and telling him he should ask N out. He immediately approached N – and gave her his number.  N proceeded to suggest they go out sometime, then immediately questioned having taken the initiative.

I empathized with her completely. Female or not, going out on a limb when you first meet someone isn’t easy. Having said that, why stand on ceremony if you’re interested enough to act on it? Inspired by N’s courage, I opted to throw a little caution to the wind myself.

Months ago, OkCupid matched me with a former colleague with whom I had a contentious (to the say the least) relationship. Ignoring our complicated history, he took a chance and invited me out for dinner. Sensing my lingering reticence, he gave me his card at the evening’s end – making it clear the ball was now in my court.

So I emailed him and proposed meeting for drinks, holding my breath a little as I hit send – and appreciating a little more what men go through when they do the asking.

He responded with an enthusiastic yes. Sometimes, it pays to break the rules.

| Girls Night Out, making the first move, Midtown NYC, OKCupid, online dating

From Online Dating To Happily Ever After

June 4th, 2011 — 6:31pm

Having had my fair share of online dating disasters over the years, I’ve come to believe that cyberspace isn’t for all singles.

I’ve become fond of saying that online dating is like gambling — there are the few that hit the jackpot and then there’s everyone else. And yet sometimes, all it takes is the lucky few to make you believe otherwise.

Over the last week, two friends of mine have gotten engaged to men they connected with online.

Galpal Julie met her fiance Brian on OkCupid last summer. In addition to being crazy about her, Brian pays close attention to the little things — as I learned when Julie shared how he proposed.

Knowing Julie is a Food Network fan, Brian surprised her with reservations at a favorite celebrity chef’s restaurant. The maitre’d came out and extended the chef’s apologies for not being on property that night to welcome them (Brian had called ahead), offering them complimentary dessert and drinks.

After a stroll across the Brooklyn Bridge at sunset, Brian honored Julie’s wishes to keep their special moment private, proposing to her in a heartfelt speech at home.

An intimate setting also provided the backdrop for Cleveland galpal Jen’s engagement.

Jen was one of the fabulous single gals I connected with during my US Dating Blitz last year. A few months later, she emailed me to say she’d met someone on Match.

“Matthew is absolutely fantastic and everything that I didn’t really think existed.”

The other night, Jen came home from work to find Matthew in the driveway with a handful of roses.

“He told me how much he loved me and how he wished he could give me flowers every day that he knew me.  I still had no idea anything was up.”

All of that changed when they went inside the entire house was covered in roses — 362 for each day they’ve known each other. Brian wrapped his arms around her and popped the question.

Both Jen and Julie had zero expectations of online dating, yet they both managed to find their ideal mate. Best of all, each of them were already living full, happy lives and fully comfortable in their own skin before meeting Mr. Right. Throw in a little help from Cupid and you can’t find a better recipe for happily ever after than that.

Congratulations, ladies!!

| finding Mr. Right, Match.com, OKCupid, online dating

Online Dating Oddball Of The Week

June 2nd, 2011 — 1:10pm

When it comes to online dating, one thing that never ceases to amaze me is how it’s a breeding ground for strange behavior. I was reminded of this the other day, with an unexpected email from a bachelor I’d connected with on OkCupid.

As I mentioned here, said guy and I were supposed to meet for drinks last month. At the last minute, he cancelled our drinks date because of work. In his text message, he also revealed that he’d been in AA for more than a decade and would rather meet for coffee.

A few days later, Mr. Coffee Lover sends me a text wishing me a Happy Passover — but makes no overture about rescheduling. I respond with thanks, thinking that was that until he sent me this missive yesterday:

“It seems your life revolves around drinking alcohol and mine doesnt. good luck in your search..no need to contact me again…really not into those that need alcohol in order to meet me. AA could use a woman like you ..”

Um, call me crazy but this seemed like a slightly extreme overreaction. And I told him as much in my response, adding that I would happily have met for an activity that didn’t involve drinking had he bothered to follow up and reschedule.

More bizarre still, the guy answers my email by informing me that he’s already found someone else who could work with his ‘crazy’ schedule.

“This new one is beginning to become an assistant for me as well for business…so best of both worlds..been having tons of fun with life…”

Which only begs the question — then why are you still contacting me?

Sigh. Simply another reason to be thankful that, for the time being, I’m offline.

| dating dos and don'ts, OKCupid, online dating

Tales Of Online Dating TMI

April 16th, 2011 — 12:36pm

In this age of social media, oversharing is an all too common practice on Facebook, Twitter and the like. Lately, I’ve experienced this phenomenon in the online dating world too — with men who, before you even meet them, give new meaning to the phrase TMI.

Take, for example, the FBI agent I connected with on OkCupid. When we spoke on the phone for the first time, I asked what seemed like an innocuous enough question–

“How was your day?”

His response?

“I probably shouldn’t tell you this since we might end up dating, but I’ve been dealing with a mouse problem.”

For the next five minutes, Mr. FBI proceeded to go on in copious detail about mousetraps, steel wool and the number of mice he’s interacted with recently.

Then there was the video production guy who cancelled our drinks date an hour beforehand because of work. In his less than apologetic text message, he said–

“For the next time we meet, I’d rather do coffee. Over 10 yrs on AA. Alcohol and me aren’t a good mix.”

Call me crazy, but some revelations are better left unsaid before meeting in person. Like the following opening gambit from an OkCupid member:

“Hot well endowed Brazilian male just for you!”

Though I had no intention of responding, curiosity led me to check out his profile. Sure enough, he indicated that you should message if you’re interested in casual sex–with the following caveat.

“Discration is a must.”

If only the same could be said in cyberspace about spell check and self-restraint.

| OKCupid, online dating

The Misplaced Art of Dating Etiquette

April 4th, 2011 — 8:51pm

Saturday, I caught up with my good friend and fellow single gal B. Over a delicious brunch at Bistro 61 on NYC’s Upper East Side, B and I got to talking about dating etiquette — and how it seems to be an increasingly lost art these days.

Case in point — the Jdate guy who B has gone out with twice. After their first date, he suggested multiple times they get together at his place so he could demonstrate his massage prowess (clearly a popular line among online bachelors, as an OkCupid member recently suggested likewise to me at the end of our first date). When B declined, he said his only free time would be following a work-related dinner — and then proceeded to be more than an hour late in showing up.

During a dinner date this weekend with an online guy, I was reminded that men too are dealing with strange behavior. My date told me he’s gone out with multiple women who’ve expected him to send (and pay for) a car service to pick them up. When I insisted on paying for the movies, he told me that was a first for him.

I was floored. For as much as I’m a believer in traditional mores when it comes to who pays on a first and second date, I also think it’s bad manners not to reciprocate. Whatever happened to putting your best foot forward when you’re getting to know someone? Has online dating reached a point where people don’t think twice about being inconsiderate of people’s time or money?

Despite what he’s experienced, my date would beg to differ. He couldn’t have been more of a gentleman — and an inspiring example of dating with class regardless of how many times you’ve experienced those who choose not to.

| dating dos and don'ts, JDate.com, OKCupid, online dating, Upper East Side

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