Category: first dates

August 25th, 2013 — 11:24am

A boyfriend of mine once had this to say about the journey you take in your career–it’s a marathon, not a sprint. I think the same wisdom applies to dating too.

I was reminded of the need for dating endurance after four consecutive equally lackluster first dates. The I recently blogged about were followed by two more. First, there was the teacher who wouldn’t stop talking about himself. Ironically, he shared that a previous woman had told him he didn’t ask her enough questions on their date. Of course, he didn’t take that feedback to heart.

Mr. Chatty Cathy was followed by a well-intentioned but awkward guy who made quite a first impression — with a terrible case of body odor.

Though bad dates make for great stories, they also make you nostalgic for the comfort zone you reach with someone when you’re well past the formalities of meeting for the first time. Over a recent dinner with a good friend, I mentioned old flame and. Rich was someone who from the get go was fun and easy to be with.

He was on my mind Friday while I worked out at the gym. Clearly, there’s something to the power of suggestion. When I later sat down at cozy UES Bar Sojourn, it just so happened Rich was there.

We fell into easy conversation — catching up on work, life and the perspective shift that comes with turning 40. Though that milestone is still five months away for me, it seemed we were on the same page about changing priorities. Among them, the need for a kitchen that allows for entertaining (typically not an option with NYC’s notoriously tiny galley kitchens).

It was a perfect night. And a much needed reminder that when it comes to dating, you really never know when a welcome surprise is right around the corner.

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August 4th, 2013 — 8:25pm

It’s often said that a first date either goes well or makes for a good story. Two recent dates with bachelors I met via ended up in the latter category.

My evening with financial trader Sean began with a rather offputting admission from him.

“I look at dates like job interviews,” he declared. “I love knowing the other person is more nervous than I am.”

“Well, I’m not nervous,” I said with a pointed smile, suspecting that additional revelations weren’t likely to put Sean in a flattering light.

Sure enough, he proceeded to talk about how he’s just so busy that he could never make time to have children, and it’s really his married friends who are more concerned about him meeting someone than he is. Needless to say, the night went downhill rapidly from there.

My discomfort around Sean was nothing, though, compared to what I experienced with school teacher Robert. In his profile, Robert said he likes a date who “talks as well as listens.” Which is why I found it particularly interesting that he spent the majority of our time together not only talking about himself but failing to ask me much of anything.

When I mentioned that my job is in hospitality, Robert proceeded to spend a good ten minutes revealing in florid detail how much he hated his past experience working for a hotel. An aside about my affinity for Broadway shows inspired him to mock several celebrity-driven musicals. And when I shared that I took a few months off to travel three years ago, he smirked.

“Did you read Eat, Pray, Love?” he asked condescendingly. “It seems like it had that effect on a lot of women.”

During our one hour drinks date (that felt more like four), Robert also treated me to a laundry list of reasons why he hates teaching and doesn’t want to do it anymore.

Call me unreasonable, but shouldn’t a first date be about putting your best foot forward? Assaulting your date with a barrage of complaints and negativity, and being dismissive about what she shares isn’t exactly appealing.

Interestingly, in our pre-date phone conversations, both Sean and Robert were inquisitive and full of positive energy. That they were neither in person reminded me how online dating is such a crapshoot. And, of course, how important it is not to be a Debbie Downer when you’re meeting someone for the first time.

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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.

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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 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 . 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.

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April 23rd, 2012 — 2:16pm

Friday night, I went out with Nominate A Date bachelor #9, Marcus, 33. Marcus and I initially connected last month, at our mutual friend .

Tall, sweet and very easy to talk to, Marcus planned a lovely evening for us that began with a leisurely stroll along NYC’s High Line. I wasn’t surprised to hear that photography is one of his passions. Marcus made a point of stopping a few times along the way so we could take in a few spectacular views,  including the sun setting behind the Hudson River.

We fell into easy conversation about our respective hometowns (he’s originally from Salt Lake City) and career transitions – his from human resources into financial services, mine from journalism to PR.  Marcus started out as a tuba player majoring in music education. I could see that because he has the kind of warm, engaging personality which would lend itself well to teaching.

The artichoke and cream pizza here is not to be missed. Yuuuum.

For dinner, Marcus introduced me to , a cozy pizza place in Chelsea, and to one of their signature dishes – artichoke and cream pizza. The mouthwatering pie is almost worthy of a blog post on its own, that’s how much I enjoyed it.

We ended up talking quite a bit about dating. When it comes to first dates, Marcus was very clear about what he considers the ground rules for them—

“Planned, paid off and partnered up.”

Meaning, he clarified, that chivalry is not dead – something he proved by insisting on treating me to dinner and graciously helping me with my coat.

Marcus asked me a lot about the blog and my various dating blitzes, managing to be inquisitive in a thoughtful, sensitive way.  He wondered what I’ve learned from it all. I found my mind drifting to various moments from each of these adventures, recalling the amazing people I met and many a-ha moments they led me to.

I told Marcus that some of the greatest lessons have been about the universality of the search for love, and the understanding shared by all singles regardless of zip code or country. I also realized how I was getting in my own way by holding on too tightly to the past.

One of the greatest epiphanies resurfaced as Marcus and I were saying goodnight.

“Let’s definitely stay in touch,” he said. “I want to hear about your future dating projects.”

I cringed when he said this.  Because it reinforced the downside of taking an unconventional approach to meeting new people – the perception that you’re only interested in adventure for its own sake. Though I have no regrets about any of my three dating projects, I am now officially done with them, happy to turn my attention toward slightly more traditional methods of connecting.

Here’s to the next chapter in my single life – and feeling completely ready for it.

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April 17th, 2012 — 9:52pm

Friday night, I met up with Nominate A Date bachelor #8 — Westchester attorney Mike, 48. Mike nominated himself after recently stumbling upon my blog.

Mike and I met up at East End Bar & Grill (photo:

As we sat down for drinks and a light bite at East End Bar on the UES, Mike was surprised to discover my day job has nothing to do with blogging.

“I thought being single was your job. I have to ask – is dating a hobby for you?”

“No,” I told him, literally having an a-ha moment about the singles scene in New York. Dating actually is a hobby for a lot of people here, a sport engaged in for its own sake rather than with any specific outcome in mind.

Divorced with two kids, Mike clearly isn’t one of those people. When I asked him if he had ever been married, he seemed surprised by the question.

“Any guy my age who says he’s never been married is either cheating or never will get married.”

I laughed at this refreshingly non-Gotham take on settling down, informing Mike that my experience of upper-40 something guys confirms it. A sharp, no nonsense kind of guy, he didn’t hesitate to reveal some of his own dating horror stories – including a relentlessly monosyllabic woman who refused to make eye contact and a bachelorette who attempted to saddle him with a pricey dinner bill on their first date.

Mike also shared how his experiences working in the military and as a cop helped prepare him to be a lawyer. I found myself thinking of my journey from journalism to PR, and being happily reminded that each chapter really does lead to the next.

When you’re single, it’s easy to feel like that’s not necessarily the case – because you don’t know where the journey is going to take you. But when I look back at the landscape of my love life so far, I see that each experience has shaped me in some way, sharpening who I am and my vision of the partner I hope to find. And in the land of dating for sport, that’s definitely something to smile about.

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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 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.

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March 4th, 2012 — 8:49pm

Today, I met up with Nominate A Date bachelor #4, personal trainer and New Jersey native SK.

SK and I were introduced through our mutual friend, the fabulous Liz of . Liz raved about what a thoughtful, caring and all around great guy SK is – qualities that all came across during our pre-date communications. We discovered mutual interests in writing and movies, and easily continued the conversation in person at Hell’s Kitchen bistro Pier 9.

Pier 9 serves up a delicious, budget-friendly brunch in a lively bistro setting

Over a delicious brunch (lobster mac & cheese, crab supreme scrambled eggs), SK and I talked about the winding road of our careers (including having both worked at 30 Rock), our passion for concerts of the 80’s music variety and nostalgia for a time when technology didn’t completely saturate our daily lives. We had some laughs about Commodore 64 computers, the impatience that texting breeds and the inevitable perils of online dating.

SK shared the story of a ex that demanded he return all of his birthday gifts, including a movie gift certificate. I admitted to cancelling post-breakup the value of a movie gift certificate I had purchased for an ex of mine. He chuckled, quipping that he would keep in mind that this is an option should future scenarios warrant it.

After brunch, we walked briskly over to Theater Row Diner, a cozy coffee shop that serves decent dessert and hot chocolate. SK asked me what I look for in a guy. I thought about it, and said that experience has taught me to look for whether someone is close to their family and friends. Because people who are tend to be pretty grounded. We both had something of an a-ha moment, realizing that paying attention to this one thing could have prevented more than one ill-fated past relationship.

As we reflected on some love life lessons not so easily learned, I found myself feeling thankful all over again for what Nominate A Date has already taught me – that you can meet some great people when you’re willing to be adventurous. And, of course, that when it comes to matchmaking, the Internet doesn’t hold a candle to your friends.

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February 27th, 2012 — 9:01pm

Wednesday night, I met up with Nominate A Date bachelor #3, New Jersey resident Kai. Our date is a wonderful example of how serendipity sometimes has a romantic streak.

Kai recently attended a disastrous speed dating event — attended solely by him and a few women. The event took place at a comedy club, so Kai ended up as the target of a few performers. He handled it so graciously that he caught the attention of my friend Annabel. Annabel has a good track when it comes to playing matchmaker – she set me up with from my European Dating Blitz.

Knowing about my adventure, Annabel mentioned it to Kai. He proceeded to send me an email that confirmed her initial impressions of him as a fun, easygoing guy. Especially when he referenced Nominate A Date in a way that indicated he had a lighthearted view of my unconventional approach to meeting new people.

Kai and I enjoyed cocktails and great conversation at Reunion Surf Bar (photo credit:

As soon as we met, I was struck by Kai’s great smile, warm personality – and knack for picking an ideal place in which to get to know each other. Our first stop was Reunion Surf Bar, a fun, flirty downstairs bar tucked away in Hell’s Kitchen. The beach hut vibe and steady soundtrack of 70’s and 80’s pop music makes you feel like you’re anywhere but in the city. Kai and I found plenty to talk about with our mutual love of travel, karaoke and taking bold leaps of faith where dating is concerned.

We traded a few speed dating horror stories before heading onto Mercury Bar, where the effortless conversation continued as we sat closer to each other. I found myself smiling a lot and feeling none of the awkwardness that often goes along with a first date.

Chemistry was the word that kept coming to mind after Kai and I said goodnight nearly five hours later. And how you never know when or where it’s going to find you, so why not just embrace that?

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February 21st, 2012 — 8:18pm

There are some nights that remind you why you stay in the journey that is dating — and should remain open to wherever it takes you. Saturday night was one of them.

Introduced for Nominate A Date through a mutual friend, 36-year-old Long Island native M and I first connected a few weeks ago. After talking on the phone, we exchanged a series of texts that revealed M’s playful sense of humor and more than a few common interests. Among them – an affinity for Scrabble, live music and beachside getaways.

Seven Bar & Grill provided the perfect setting for a perfect first date

The conversation continued effortlessly when we met up at Seven Bar & Grill in Midtown West. M greeted me with a kiss on the cheek and gallantly took my coat, as I found myself thinking he was even cuter in person than his Facebook profile picture.

Over a delicious dinner (tuna tartar, lobster bisque soup, pan roasted snapper with lobster crushed potatoes), we bonded over our appreciation for good food and of course dessert (we shared tiramisu and coconut rice pudding). I also learned more about M’s work as a contractor, his longstanding love of guitar playing and why seeing an 80’s cover band – my suggested post-meal activity – wasn’t his first choice.

I happily said yes to his proposed alternative, going to see the Channing Tatum-Rachel McAdams romance, “The Vow.” During the previews, M leaned over a few times to make small talk. I could feel the kind of click that happens when you’re genuinely having a good time with someone.

We both enjoyed the movie – as far as on-screen love stories go, this one managed to be sweet without being too cloying – and, much to my delight, M didn’t let his hour-long journey home cut our evening short.  Our last stop was Houndtooth Pub, where we talked about Caribbean cruises, spiritual retreats and outgrowing the antics of being in your twenties.

It was after 1am when I walked M to Penn Station. Later, I texted him to say thanks for a great night and for coming into NYC.

“Worth the trip,” he replied.

The feeling was more than mutual.

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