Category: online dating

June 22nd, 2014 — 11:17am

I’ve often said that, for all its convenience, texting has become the death of romance. The flip side—it also makes it much easier to detect when someone you’re dating isn’t a good fit.

Two recent dates with two bachelors I met on HowAboutWe illustrated this fact.

After going out twice with , I wasn’t quite sure if the chemistry was there for me. Still, at this stage of dating, I usually give it three dates before making a determination. After all, chemistry can take a little time to develop, right?

So I schedule date #3 with S. When I reach out (yes, via text) day of to confirm, he says he ‘totally forgot’ we had plans and asks to reschedule. I’m not impressed but grudgingly say yes. On the rescheduled day, S initially texts to say we’re on for dinner. Then, a few hours later, he texts again, saying–

“You’re not going to believe this, but I have close out a business event tonight so I have to cancel. L”

I honestly wasn’t sure if I believed him. What I was sure about was that S probably felt my reticence and was accordingly blowing me off.

Bachelor #2, Randy, was very obviously from the get go just looking for uncomplicated fun. The chemistry was definitely there and so was a mutual appreciation for 80s music. Nevertheless, I set some boundaries after date one, declining Randy’s offer to have our second date happen at my place.

After a fun evening of dancing the night away at Pyramid Club in NYC’s East Village, Randy continued texting me. His only invitation to get together, though, came late on a Friday night.

“Wanna watch the Late Show together?”

I declined, later telling him I enjoyed his company but wasn’t interested in a fling.

“Where did you read the words hookup in my text?” he wrote testily “I didn’t say anything and it’s not right to assume anything.”

True. It’s not right to make assumptions, especially with a medium like texting that’s makes miscommunication an all too common thing. Sometimes, though, it communicates incompatibility loud and clear—and, fortunately, very quickly.

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May 26th, 2014 — 7:19pm

As I mentioned in my last entry, I’m thoroughly enjoying the feeling of renewal that comes with a new season. Spring is a wonderful time to make a fresh start – and that’s what I’m doing on several fronts.

I recently went on two dates with guys I connected with on Much like most of the bachelors I’ve met through the site, both were personable, fun and engaged in taking advantage of what this great city has to offer. That makes sense given HowAboutWe’s premise: posting date activities and meeting likeminded people with similar interests.

Still, much as I have enjoyed the men I’ve met on HowAboutWe, I am also ready for a new online dating venue. Dating websites have inevitably become the virtual equivalent of the bar scene. So, after a while (in this case almost a year) of frequenting one, you can’t help wanting to try something else.

I recently stumbled upon a commercial for – no joke –, a website targeting the agriculturally inclined. I’m not in their target demographic, of course, but it is equal parts fascinating and disturbing how niche-oriented the online dating world has become. Call me cynical, but I think this checklist approach to finding love is only making singles more disconnected.

If it sounds like I’m a little weary of the process, not to mention ruminating about it, well, I am. Which is why I’m in the midst of another spring makeover project: revamping my little corner of the blogosphere.

Next month, I will unveil a brand new online direction for this single gal in the city. I will be celebrating this milestone with a series of great giveaways. Looking forward to having you along for the ride, more details to come soon!

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September 16th, 2013 — 8:54pm

Like many so singles, I have a love-hate relationship with online dating. Though it can introduce you to a variety of people, it also seems to have a higher volume of inappropriate behavior than the offline world.

In a virtual universe where anything goes, you can find yourself on the receiving end of these bizarre antics quite regularly.

OkCupid is a magnet for bachelors who don’t appreciate that less is more when you’re getting to know someone. One recent Okc member followed up a fun first date with an invitation to have lunch with him and his sister. I politely declined. He followed up with an explicit late night text message, blaming it on being “drunk, haha!”

Then there was the psychologist I chatted with on the phone. I asked him how his weekend was. He responded with a lengthy description of his father’s enlarged prostate. And a wistful lament for the days when he trolled nightclubs picking up women on the dance floor.

It is one of my single relatives, though, who can claim the most off putting initial conversation with an online bachelor. He had a very specific proposition for her–

“Would you like to Skype in the nude?”

Seriously? Whatever happened to good old fashioned dating etiquette? I know we live in a modern era of sexting and so on, but why is there such a mad rush to replace romance with raunch?

As you might expect from the above, I’m more a fan of taking things slowly. Or at the very least, having the courage to make your x-rated requests in person.

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September 1st, 2013 — 1:40pm

When you’re single, it is inevitable from time to time that well intentioned people will offer to set you up. What I’m increasingly discovering, though, is the gesture rarely materializes.

Over the last couple of months, three different people have mentioned bachelor friends who they would like to introduce me to. Knowing the trepidation that often comes with trying to play Cupid, I reassured each of them by sharing my no-fault matchmaking policy – i.e., no sparks, no problem. After all, mutual chemistry is unpredictable enough that you can’t really hold someone accountable when it doesn’t happen.

I also make it a point to say I’m flexible about how the connection is initiated – open to either providing my contact info or reaching out to the bachelor in question. In a previous life, the traditionalist in me would have insisted on the guy initiating communication. But having been through the anything goes world of online dating, speed dating and just about everything in between, I’ve learned you can’t stand on ceremony and be completely rules driven if you want to meet someone new.

If only matchmaking-minded folks were equally progressive.

Two of the recent would-be Cupids backpedaled as soon as I indicated my openness to taking them up on their offer. They suggested it would be “less pressure” if I were to meet their bachelor friends in a group setting. Less pressure, no doubt, on them for the matchmaking attempt to be successful.

Why create obstacles to the very objective you’re supposedly trying to facilitate? And why state you’re inclined to play matchmaker if you’re not going to actually follow through on it?

Some would argue it’s the thought that counts here. I say, unless you’re actually willing to put words to action, it’s probably best to keep any matchmaking thoughts to yourself.

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August 18th, 2013 — 8:53pm

When it comes to online dating, I’m a big fan of anything that makes it easier to take the connection offline and in person.’s Stir events across the U.S. are geared toward this and now the website is adding a game night series to the mix.

Match has partnered with seven board game manufacturers to provide singles with a combination of icebreakers and party games. Having attended a few happy hour Stir events and been underwhelmed, I think this approach sounds more effective, not to mention a lot more fun. has launched a game night series of events (photo courtesy:

To make it easy to concentrate on mingling and enjoying the game, tables are set up in advance and include easy-to-read game instruction cards, so you don’t have to fumble around with lengthy, confusing directions.  facilitators lead singles through the games.

Players rotate from table to table between rounds, giving everyone a chance to mix and mingle while playing up to seven different games.  Attendees are also provided with a selection of games to play on their own as icebreakers, while connecting with other singles.

Game night events are taking place now through the fall at bars and restaurants in select cities including NYC. Stir events are open to members and their guests. I’m looking forward to checking out the September 5th outing featuring musical game Spontuneous. Stay tuned for a recap.

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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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April 28th, 2013 — 9:10pm

Thursday, I enjoyed a girls night out with my good friend Lauren.

After a brief stop at Faces & Names bar and walking past the NFL Draft red carpet on Sixth Avenue, we settled at the bar of Del Frisco’s in Rockefeller Center. Over a round of Blue Moon and some shared appetizers (cheesesteak egg rolls and tuna tartar tacos…delish), we talked about career moves, bad dating behavior and my most recent speed dating experience.

I’ve said it here and to other singles many times – speed dating is a thousand times better than dating online. Still, some outings are better than others and this particular one was a very mixed bag.

Most of the 15 guys I met were first timers bleary eyed from the frenetic pace. Many used their four minutes to ask questions straight out of (where do you work? What do you like to do when you’re not working? etc.). Others didn’t know what to ask. Among the more memorable bachelors: a 67-year-old who laughed a little too hard as he shared that he is divorced because he likes dating thirtysomething women; a cute British expat whose charm rapidly dissipated when he remarked how there are so many more single women than men in NYC.

Inevitably, if you do speed dating multiple times, you run into familiar faces. I cringed when I spotted a guy I dated briefly back in January who went all X-rated in his sweet nothings on date #2.  For a city of 8 million people, New York is way too small sometimes.

Which is why I’m feeling especially thankful for the gradual yet seismic attitude shift I’ve been feeling lately when it comes to finding love. A combination of spring weather and Amy Spencer’s uplifting book about dating optimism, is fueling the change.

There’s definitely something to be said for positive thinking. In the last week alone, I’ve reconnected with an old flame and met a matchmaker-inclined florist.

I can’t wait to see what happens next.

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March 10th, 2013 — 8:22pm

(photo courtesy:

As the first quarter of 2013 races to a close, I’m happy to have stuck to one of my New Year’s resolutions – speed dating more often. With other, more time intensive resolutions being a work in a progress, this one is proving to be a lot of fun. And a reminder of how important it is to inject some fun in to the dating process.

Readers of this blog know I’ve been a big fan of speed dating for years now. And I’ve also found time and again that it’s the number one thing singles tell me they want to try but haven’t. Interestingly many of these same people have done online dating. I guess it’s less daunting to flirt via cyberspace than to face the prospect of a dozen or so mini dates with complete strangers. In my experience, though, the payoff is much, much greater when you get back to basics and interact with fellow singles in person.

There are so many advantages to speed dating. First, of course, is the obvious – meeting a lot of people in a short space of time. Second, it gives you the opportunity to practice your flirting skills and elevator pitch about yourself, always a good thing in the competitive dating jungle that is New York. Perhaps the most important thing, though, is it levels the playing field.

As a thirtysomething single woman, it’s very easy to think you’ve got the market covered on feeling frustrated with what it takes to make a meaningful romantic connection. A quick chat with just about any guy you meet speed dating reveals that’s most definitely not the case.

Even though, statistically speaking, the odds are more in their favor, single guys go through their ups and downs just like we do. And I can’t help thinking that discovering such common ground helps break down the walls that often divide us in this great city where playing it cool is practically an Olympic sport.

So if you’ve been on the fence about trying speed dating, now’s the time to jump off and give it a try.

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February 23rd, 2013 — 8:45pm

There are some days that make you fall in love all over again with your hometown. For me, Wednesday was one of them.

It started with a visit to Alice Tully Hall at Lincoln Center, where I joined hundreds of fellow hospitality professionals for NYC & Company’s annual meeting.

NYC & Co. annual meeting generated excitement for the city’s soaring popularity as a travel destination

Speaking of new finds, my next stop was the Museum of Art and Design in Columbus Circle, where I met up with business associate Andrea. We headed up to Robert, the museum’s penthouse restaurant with fantastic views and a sleek, modern décor that still manages to be both warm and inviting.

The Robert is a fabulous nightspot

Andrea shared the news that she recently married, which led to a lively conversation about the unexpected journey to finding Mr. Right.

Andrea met her hubby on JDate a year ago, admitting that on paper, he seemed completely different from her usual type. She decided to give him a chance despite opposite schedules and some challenges from living in different boroughs (he’s a Brooklynite, she lives in Manhattan). She said the right relationship is worth the effort — and it tends to happen pretty quickly when you come upon it.

My friend Rachel would no doubt agree with her. When I caught up with Rachel in London last August, she was single and not dating. Just six months later, she’s engaged and planning a 2014 wedding.

Andrea and Rachel are about ten years apart in age, which I can’t help viewing as an encouraging reminder that — contrary to how single women over 35 are often portrayed in the media —  there’s no expiration date when it comes to finding love. You just have to keep yourself open to it. That and embracing the digital possibilities for romance today.

Congratulations, ladies.

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February 17th, 2013 — 5:06pm

Wednesday night, I headed over to David’s Tea on the Upper East Side for cocktails and conversation in celebration of eFlirtExpert Founder Laurie Davis’ fabulous new book, .

eFlirtExpert Founder and author Laurie Davis shared some online dating tips with the crowd

Having worked with nearly a thousand clients and connected with her future hubby on Twitter, Laurie knows plenty about dating in the digital world. Love At First Click is a brisk, engaging read packed with great tips for finding love in cyberspace. Laurie covers everything – from choosing the website that’s right for you and creating the perfect profile to netiquette rules.

All smiles with the author

After reading her book, you won’t have to wonder about whether to wink or how to use emoticons when flirting via email. The best compliment I can give is that Love At First Click has made me consider a  return to online dating. Laurie dispenses her practical, proven advice like an old friend whose wisdom you can’t deny. Her book is a must read for singles navigating the digital dating world.

Laurie and I talked about how excited we are for Tuesday’s First Date how-to event at THE LCL: Bar & Kitchen at the Westin New York Grand Central. Laurie will be joined by her fiancé Thomas Edwards (a.k.a ) and a team of Starwood hotel concierges, sharing their expertise about where to go and what to do on a first date. for more info and to RSVP.

I also had the pleasure of catching up with CeCe of . We talked about work, what’s new in social media — I didn’t know about hot new video app Vine – and adventures in speed dating. I told CeCe about the guy I met at HurryDate last month who called me at work weeks later, soliciting a business lead then clumsily asking me out as an afterthought.

Here’s hoping my next speed dating outing in March will be more successful. In the meantime, I think I might be paying a visit to OkCupid…

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