Category: OKCupid

A Second Date With A Semi-Surprising Outcome

December 8th, 2012 — 7:40pm

My second date with Long Island bachelor and OkCupid member E began much like the first – at a fabulous nightspot in Chelsea.

We met for drinks at The Darby, an upscale jazz club and restaurant with rich, elegant décor and great music. As we clinked glasses, E said I looked pretty and we made easy small talk about the holidays and our plans for the evening.

For dinner, E chose Crispo, a first-class Italian bistro with a cozy main dining room featuring exposed brick, a waterfall and wrought iron chairs. The food was amazing – I had black truffle ricotta ravioli and we shared a sublime tiramisu for dessert. Along the way, E asked a lot of questions and listened intently as I told him about my travels to Australia over the years and what I learned during my U.S. Dating Blitz.

Crispo serves delicious, authentic Italian fare (Photo Courtesy:

I found myself thinking maybe I had read too much into his gay-related observations on date #1 — until we got to Canal Room down in Soho.

As we waited for awesome 80’s tribute band Jessie’s Girl to take the stage, E quoted some advice a friend had shared with him–

“’If you like this girl, don’t tell her you like Neil Diamond.’”

While I’m processing why he’s telling me this, E reflects on how popular tight jeans were during the 80’s – and gestures toward the rear end of a guy in front of us who’s wearing them.

At this point, I can’t ignore the fact that my gay-dar vibe is sounding an alarm. I try putting that aside once the concert starts, doing by best to just enjoy Jessie’s Girl’s energetic set of 80’s classics. But when E leans over – twice – to comment on the band’s muscle-shirt clad male backup singer, my patience begins to wear thin. Nothing’s a bigger buzzkill than having your date make eyes at other men.

E and I shared an awkward cab ride back uptown.

“I’ll talk to you soon,” he called out as he shut the door and I knew that wasn’t going to happen. Because clearly, he has a few things to figure out when it comes to who exactly he wants to date.

Though I managed to eventually find the humor in this unexpected episode, it also served as a cautionary tale of what can happen when you rely too heavily on the Internet to find love. I’ve said it many times and it bears repeating: online dating is a lot like gambling. There are the lucky few who hit the jackpot and then there’s everybody else. I, for one, have had my fill of cyberspace-instigated dates. So I’m officially taking my online profile down and making a New Year’s resolution to get offline and back out there again.

The quest for love continues.

| 80's cover band, Canal Room, Chelsea, new year's resolutions, OKCupid, online dating, second dates

A Surprising First Date

December 5th, 2012 — 10:04pm

It’s no secret that online dating has its fair share of surprises. And that most of those surprises are because people aren’t always how they appear in a profile. I was recently reminded of this after connecting with E on OkCupid.

E and I seemed to click in our initial phone conversation, which breezed by for over an hour. During that time, E admitted he actually lives in and is from Long Island — not Manhattan, as his profile states. Knowing the geographic snobbery that is all too common here in NYC, I understood the minor mistruth and thought nothing of it.

Il Bastardo: this popular bistro in Chelsea is perfect for a first date

We met for drinks at Il Bastardo, a cozy Italian bistro in Chelsea with a lounge vibe. When I arrived at the restaurant, he greeted me warmly, making mention of both my dress and my earrings. We easily picked up where we had left off in our phone conversation, talking about our mutual affinity for James Bond and the challenges of dating in your thirties.

It was around this time that E revealed he is actually 44, not 39 as his profile states. A red flag went off — lie #2, I thought to myself suspiciously — but I brushed it off when he talked about age discrimination in the New York dating scene. Having once been a twenty something woman dating upper thirty something guys, I couldn’t argue with his reasoning.

So the easy banter continued, as a second round of drinks led to dinner and we found ourselves sharing relationship war stories. When I mentioned my history of dating older men, E talked about an older woman he was involved with for awhile.

“She told me that when she first met me, she thought I was gay.”

This seemed like an unusual anecdote to share but, once again, I tried not to jump to conclusions. After all, isn’t that we’re often accused of as thirtysomething singles — being too picky, too quick to make snap judgments about the opposite sex?

E briefly excused himself to go to the bathroom. Just before I followed suit, he made a point of telling me it was a unisex facility — and that he was once almost propositioned by two men who disappeared into a stall in there.

Again, red flag alert. Could it be, I wondered, that E was as interested in men as his profile claimed him to be in women? I was, well, befuddled. His words seemed to say one thing yet his actions communicated something else, especially when it came time to say goodnight. E leaned in for a kiss that left little room for questioning.

Date #2, however, was a completely different story.

| Chelsea, first dates, OKCupid, online dating, online dating profiles

The Happiness Ripple Effect

September 12th, 2012 — 9:28pm

As I mentioned in my last couple of posts, I have a new job that I love. And it’s making me rediscover just how much of a ripple effect being happy in one very important area of life.

During a recent dinner out with good friend who, like me, was recently liberated from a hellish work environment, she pointed out my changed demeanor.

“Now I know why people have been telling me I look completely different. You look so much happier,” she said.

Just like the changing temperatures and start of fall, I feel like I’m in a new season myself. Looking forward to every workday has given me a renewed energy to jump start non-career related goals. And the universe is more than meeting me halfway.

Last night, for the first time in months, I had a great conversation with an OkCupid bachelor, one that resulted in an upcoming date. Today, I learned that I’ll be doing a second piece for Latina Magazine (look for it in the February 2013 issue!). And I’ve made a small dent in my mission to shed the extra pounds I picked up over the past two years.

Simply put, I’d forgotten how being content at the office can spark feeling that way outside of it too. And I’m beyond thankful to the Westin New York Grand Central for reminding me.

| new jobs, OKCupid, online dating, Westin New York Grand Central

The First Date Dilemma

June 3rd, 2012 — 3:20pm

Like most thirtysomething singles, I’ve been on my fair share of first dates. And yet, it doesn’t seem to get any easier to answer the unavoidable first date question — how to say goodnight?

Of course, there’s no right or wrong answer because so much of it depends on how the date goes in the first place. A recent evening out with OkCupid bachelor JC reminded me that more often than not, parting company can be more than a little awkward.

The date itself seemed to go well — decent conversation at a cozy wine bar, with a few laughs along the way. JC indicated he was disappointed that the bill came while I was in the bathroom. When I informed him the waitress brought it without any prompting from me, he said–

“The night doesn’t have to end here.”

And so, we went on to a nearby bar for one more round before heading toward the subway. As we approached the station entrance, JC said regretfully–

“Oh, this means our date is almost over!”

I assumed that he meant he’d like to get together again. Which is why I was more than a little surprised when his parting words were–

“Don’t be a stranger.”

I didn’t quite know what to make of that one. Did he want to get together again? Was he trying to gauge whether I was interested enough to make the next move? Granted, that’s one of the trickiest parts of a first date — who takes the leap of finding out if there’s going to be a second one? Experience has taught me that even though the so-called ‘rules’ say that responsibility belongs to the guy, men don’t always want it.

Not too long ago, another OkCupid guy ended our first date by handing me his business card. We didn’t exactly click, so I understood him wanting to put the ball firmly in my court.

Then, more recently, there was my final Nominate A Date bachelor Marcus. Despite asking several questions about whether I’m relationship ready, Marcus made it clear he wanted friendship only — inviting me to keep in touch about my dating projects (ugh).

But the most surprising conclusion to a first date I’ve ever experienced happened more than a decade ago. After hours of effortless, flirty conversation and palpable mutual chemistry, Southern Illinois cutie Steve said goodnight with….a handshake. I remember being completely floored (especially since I was so convinced about a forthcoming kiss, I’d discretely popped a breath mint minutes before).

Steve and I later had a good laugh about it after smooching at the end of our second date. And so began a wildly passionate romance that evolved into a friendship which endures to this day.

The longer I’m on this journey called singlehood, the more I realize that you really can never predict when, where or how romance is going to ignite. Sometimes a lukewarm goodnight means it’s just not happening, sometimes a handshake is a precursor to being completely smitten. And the only way to find out is by braving first dates, awkward moments and all.

| dating rules, first dates, OKCupid, online dating, Southern Illinois

An Online Dating Misstep

April 3rd, 2012 — 7:08am

When it comes to online dating, I’m all for cutting to the chase and cutting down on back and forth communication. Having said that, I think sometimes people are a little too quick to skip the basics — like, for example, actually reading a profile before initiating contact.

I recently received a lengthy message from an OkCupid guy who, in his haste to connect with as many women as possible, chose an unusual approach: a form letter. No personalization, just a five-paragraph missive along the lines of a job seeker who hasn’t taken the time to do his homework. Here’s an excerpt:

“Hi, my name is [A], I’m almost 35 and live in Northern NJ about 45 mins from Lincoln Tunnel, GW Bridge and Holland Tunnel… I am single, never married, never engaged, and no children, last relationship was a few years ago since then I have been focused and busy working on myself and putting my ducks in a row… You know the whole career, then mortgage and finance a house, and then eventually meet the right woman… Please do not think this means that you are the right woman. I just am trying to muddle through the dating scene as an adult. From the pictures I saw there was definitely an initial attraction, and I would love to know more about you. Like what is your name? Do you have any siblings? When was your last relationship? How long have you been using OKCupid?

I prefer quality to quantity, and I’d rather be alone and single then settle and be miserable. I do have to say I would really enjoy getting to know you better, perhaps online messenger, or via cellphone calling or texting. I believe the first step to a good foundation is communication. I believe communication is important with friendships, relationships, even networking. I do text but I prefer to use the phone so I can really get a feel for the person and vice versa. So I will be the first to ask if you would like to talk and get to know each other better. I do understand I may not meet what you are looking for, but you should be open to giving me a chance… Oh and by the way, if you really don’t think I’m your cup of tea, I just ask for a polite email saying Thanks but no thanks…”

Apart from being a bit wordy, there was one problem with this introductory missive — A and I already connected seven months ago. We exchanged emails for weeks, then played phone tag for nearly as long. Though none of this culminated in a date, we communicated enough that it’s a little strange A chose to include me in his mass messaging.

A male friend of mine says, during his online dating days, he used a spreadsheet to keep track of everyone he connected with. After receiving A’s misdirected introductory message, I think he may be onto something.

| OKCupid, online dating

Nominate A Date (Sort of) #7

March 24th, 2012 — 3:04pm

As I recently mentioned, would be Nominate A Date # 6 went MIA. So, in the adventurous spirit with which I started this journey, I opted to loosen the parameters and go out with Kash, an OkCupid member who nominated himself.

Earlier this week, we met up for drinks on the Upper East Side. Much as he seemed in his profile, Kash was well spoken and thoughtful, happy to share his take on writing, what he enjoys about his day job at a law firm and how he manages to juggle work with finishing up his master’s degree.

At 30, Kash falls within the broad age spectrum (27-47) I’ve been open to for – which also happens to be beyond my dating comfort zone (38+).  Longtime readers of this blog know I’m a big believer in shaking things up. The older I get though, and the more miles I log in this journey called singlehood, the more I am realizing that there’s nothing wrong with knowing what you want — and what you don’t.

As I listened to Kash talk about his aspirations and newness to the online dating scene, I was reminded of why my dating type skews older than he is — because it usually means having more in common and, for me, more of what it takes to spark a genuine attraction. Though I’ve had some fun flirting with younger guys, I’ve always been most drawn to men who are my chronological peers or older. Being at the same life stage makes romantic chemistry feel grounded in something more substantial. Especially when the connection begins through mutual friends instead of online.

With only a few weeks left of Nominate A Date, I’m appreciating how this process has taken my love life offline and somewhere a lot more fun than cyberspace. Cupid tends to have a much better track record when he’s not confined to a computer.

| Nominate A Date, OKCupid, online dating, Upper East Side & Nominate A Date #5

March 11th, 2012 — 6:12pm

As someone who is bone tired of online dating, I’m a big fan of websites that make it easier to connect offline. So I was excited to hear about, a site created by veteran bartender Teresa Rivera that connects members and suggests ideal bars based on a variety of variables.

Each bar has a profile highlighting hook-up potential, guy-to-girl ratio, vibe, etc. The website’s team also stalks the City’s top bars, so that members can see the hottest venues for a particular evening. During the registration process, asks you to fill out a brief profile with info including favorite spots in the city, neighborhood, and what qualities you’re looking for in a match, etc. One of my favorite features — an “Anonymous Check Out” button that enables members to view matches while remaining discreet.

When my date for this weekend fell through, founder Teresa graciously and quickly came up with an alternate candidate – 34-year-old J, a good-looking, soft-spoken personal trainer and Connecticut native.

Del Frisco's Grille in Rockefeller Center has a much cozier vibe than its sister restaurant on Sixth Ave nearby

J trekked in from the Bronx for our drinks date, which got off to a good start with him guessing that I’m closer to 30 than not. We met up at Del Frisco’s Grille in Rockefeller Center, which has a fantastic cocktail menu and ideal low-key ambience for conversation. J filled me in on his upcoming trip to South Beach, why nothing and no one comes between him and an Oakland Raiders game and what he doesn’t like when it comes to food.

He also mentioned a seven-year relationship. His ex-girlfriend actually came up a handful of times. Even though it happened organically, it got me to thinking about mentioning old flames on dates in general. It’s a topic that has surfaced a few times since I started Nominate A Date about a month ago. One guy did it only in passing as we were comparing notes about online dating disasters. Another bachelor, the only one I’ve gone out with multiple times, spent the last part of our third date telling me about his month-long stint on OkCupid.

Admittedly, these stories can be amusing at times (after all if they weren’t, dating blogs wouldn’t exist). I’m just not so sure the first few dates with someone should be a forum for them. Because, frankly, it’s a buzzkill.

| first date ettiquette, first dates, Nominate A Date, OKCupid, online dating, Rockefeller Center

The Mystery of The One Sided Date

February 1st, 2012 — 9:31pm

When it comes to first dates, it’s safe to say the whole point is for two people to get to know each other. Which is why I remain baffled whenever I encounter someone who perceives it more as the chance to have an audience of one.

Over the years, I’ve had a handful of first dates during which the guy pretty much monopolized the entire conversation. There was the once engaged bachelor who, clearly still in heartbreak mode, opted to share chapter and verse about what precipitated the breakup. Or the chatty piano player who barely let me get a word in edgewise, later admitting via email that he tends to talk a lot when he’s nervous. Both completely understandable scenarios – unlike my outing with an OkCupid member the other night.

His profile was so well written and detailed that I didn’t think too much about its copious length. Especially since his introductory email managed to sound flattering yet sincere. When we spoke on the phone, he spent most of our 20-minute chat telling me about his extensive wine expertise. Though this was a major clue into how much he likes to hear his own voice, I opted to give him the benefit of the doubt. Maybe he was nervous, I told myself. And, after all, aren’t we thirtysomething women often accused of not giving men a fair chance?

So I meet Mr. Wine Expert for drinks. Not surprisingly, he selects a perfect venue in Midtown — a unique hybrid of wine bar and sports bistro that was comfortably quiet on this particular night. I compliment him on being a connoisseur, to which he replies with an explanation of the word’s true origin and that it doesn’t always have a positive connotation. And then, for the next two hours, he did not stop talking. About the differences between grape varietals, what makes beer Belgian, why he speaks several languages and why he hates being asked what his favorite restaurant is.

I tried a few times to interject, but each time he made sure the conversation reverted squarely back to him. As I sat there, I couldn’t help wondering – would this monologue ever end? And, more importantly, how could I make a fast exit in time to get home and watch the SAG Awards?

The one redeeming part of the evening? I only missed the first 20 minutes of the awards.

| first date, first dates, OKCupid, online dating, online dating profiles

Relearning The Rules of Online Dating

January 2nd, 2012 — 7:31pm

(photo courtesy:

With the new year here at last, I’m getting back out into the dating scene. That means going online again — and relearning some of odd rules of dating in cyberspace.

Beware of weird/cutesy profile names: Though not always the case, it’s safe to say that an unusual profile handle often equals an equally unusual person. Among the more colorful guys I’ve heard from — monkey_vs_robot, out_to_late_NYC and easternspice4u.

Being overly familiar isn’t a turn on: even after online dating on and off for years, I’m astounded at how many people don’t know the difference between flirting and creepy come ons. Among the recent opening gambits I’ve received: “Hi Honey” and “You are yummy.” In a word, ewww.

Lengthy emails and chat mean nothing: Many bachelors online seem to favor back and forth communicating that never goes anywhere. Case in point — the fortysomething hotel exec who followed up a five paragraph email and one hour conversation with…zilch.

Disappearing and reappearing require no explanation: In a dating medium designed for short attention spans and shopping around, this is an all too common occurrence. My favorite recent example — the Connecticut bachelor I chatted with who said he would call me back but never did, only to resurface in an email a month later. I invited him to give me a call. “Will do,” he says. He doesn’t then emails me again three months later. “Hi Melissa, long time!” he writes, oddly given that he disappeared twice. 

Speaking of disappearing acts, not all are the same. I’m actually meeting up this week for date number three with a charming, cute OkCupid bachelor — three months after date number two took place.

Here’s to an eventful 2012, on and offline!

| OKCupid, online dating, online dating profiles, online flirting

What I’m Thankful For

November 26th, 2011 — 4:30pm

Thanksgiving may be over but I find myself still thinking about what I’m thankful for – and feeling hopeful that this holiday season will bring a gift that’s been eluding me for awhile now.

Every year, I count my amazing family and friends at the top of my blessings lists and this year is no different. In the absence of my beloved parents – whose loss I continue to feel acutely – I know I am doubly fortunate to have so many wonderful people to count among my nearest and dearest.

I’m just back from spending the holiday in Delaware with my brother and sister-in-law, whose love, warmth and understanding make every occasion together one worthy of celebration. Tonight, I will trim my tree with galpal Faith, the kind of friend who makes good times better and difficult times more bearable. Tomorrow, I will head to New Jersey to visit my Aunt Nancy and Uncle Johnny, two of the most kind and generous souls you could ever know.

Yes, when it comes to loved ones, I can say I have an embarrassment of riches. Their support and encouragement are what make me optimistic that I can give myself a gift as 2011 winds down – getting back in the proverbial saddle again.

Readers of this blog know I’ve spent much of this year on sabbatical from dating (a few half-hearted forays into OkCupid notwithstanding). It was a break that I needed, one that gave me the opportunity to reconnect with myself and concentrate on the many pursuits that fill my life. Now it’s time to take my own advice and get out of my comfort zone – i.e., take dating off the back burner.

With less than two months until my 38th birthday, I can’t deny I’m more than a little weary of this merry go round. But I know that’s no longer a good enough reason to sit on the sidelines anymore. So, I am bidding a not-so-fond farewell to OkCupid and all of its grammatically challenged, disappear act pulling members and saying hello to new adventures of the offline kind. Here’s to a holiday season and 2012 full of them.

| dating fatigue, dating in your thirties, OKCupid, Thanksgiving

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