Category: dating rules

In Defense of Old School Dating Rules

June 5th, 2014 — 9:31pm

I often say that I miss dating in the nineties. Recent experiences reminded me of why — and how murky the dating landscape has become.

After connecting with a guy online, S, we met up for drinks. As the evening progressed, our solicitous waiter repeatedly asked if we wanted to order food. S cut him off each time without even asking if I might want to share something.

When it came time to plan date number two, S asked me to suggest a venue. Applauding his excellent first date choice, I insisted he choose. He did. Drinks or dinner? I wondered.

“Up to you,” he texted back.

“Your call,” I replied.

I could feel my frustration mounting as I texted that. Whatever happened to a healthy dose of manly initiative in romance? Why does it feel like you have to strongarm a guy into courting you these days? The answer, of course, is that the old fashioned rules which once defined dating seem to have gone by the wayside – making it more difficult than ever to truly connect.

In this era where your next flirtation is only a click away, it’s no surprise that today’s dating culture is a decidedly lazy one. Popular wisdom encourages this, repeatedly telling us women that our expectations are too high, that we are naïve and unreasonable to want the wooing of pre-texting days.

I’ve lost count of how many times I’ve been told to lower my expectations. But at what point does accommodating post-modern dating rules (or lack thereof) begin to cross over into compromising what you believe in?

S did eventually take the lead with my encouragement. Which made me see an upside to these role reversals in dating – being free to speak your mind about what you want.

If only it didn’t feel like a time machine was required to find it.

| dating, dating dos and don'ts, dating rules

Why I Don’t Go To Singles Events

May 4th, 2014 — 8:56pm

One of my dating resolutions this year was to declare a moratorium on going to singles events. Friday night, I was reminded of the many reasons why.

A good friend of mine asked me to join her at a 40+ singles mixer. As she hadn’t been to one in a while, I gladly obliged, telling myself I was going strictly to be a supportive friend. Of course, despite my prior experience with these things, a small part of myself couldn’t help thinking—maybe this one will be different.

The venue (Pranna in NYC’s Flatiron District) and price point ($20) were both great. The crowd that turned up?

Not so much.

Pranna in NYC's Flatiron District

Pranna in NYC’s Flatiron District

Simply put, the event was a perfect microcosm of what makes dating in New York so frustrating. Women far outnumbered the men. We were also the ones who were obviously expected to do the heavy lifting.

Over and over again, I watched women approach men as said men either stood idly by waiting for that to happen or looked down at their phones. Though everyone received a list of mostly odd icebreaker questions (“have you ever cried in a movie theater?”), it was only the women in attendance fast and furiously working the room with it.

My friend wryly observed that the entire scene felt like a repeat of awkward high school dances. I said this was decidedly worse. At least in high school, guys eventually stepped up to the plate and took some initiative. Yes, I know times have changed, women feel empowered to make the first move and are more independently minded, etc. etc. But I can’t help wondering, at what cost? Has all of this progress come at the expense of good old fashioned romance?

As Savvy Auntie Founder Melanie Notkin writes in her fantastic memoir Otherhood, men mistakenly assume that our more equal footing in the workplace means we’ve somehow lost our femininity when it comes to dating and relationships. News flash—we haven’t. We still want you to plan a first date (maybe even a second one too).  We still need to be courted (instead of being asked from day one, ‘what do you want to do tonight?’). None of the rewritten rules have changed any of that.

As for singles mixers like the one I just went to, I have another pet peeve: no free cocktails. Considering how much work it takes to mingle these days, $20 should at the very least cover a shot of liquid courage.

| dating rules, Flatiron District, Pranna restaurant, singles events

Celebrating A Fabulous New Dating Advice Book

June 2nd, 2013 — 9:16pm

Wednesday night, I attended a press preview for Andrea Syrtash and Jeff Wilser’s new book,

All smiles with co-authors Jeff and Andrea

All smiles with co-authors Jeff and Andrea

Held at THE LCL: Bar & Kitchen and sponsored by Movado, the lively event gave me the opportunity to catch up with some of my favorite fellow bloggers: Nando, and Yolanda Shoshana. This trio’s sass and smarts never fail to entertain.

While enjoying cocktails and some delicious hors d’oeuvres, we talked about the teenage-like thrill of a great first date, the complicated journey of exiting a difficult romance and the myriad joys of being in jobs that we love. Nando also shared a hilarious tale about the interplay between his two pet birds that proves male-female posturing in relationships happens among the animal set too.

Movado treated all attendees to a fabulous gift — a watch from their colorful ESQ ONE collection. I opted for a classic white timepiece which I am loving. Thank you, Movado!

Tres Chic: Movado's ESQONE timepiece

Tres Chic: Movado’s ESQONE timepiece

I also had the pleasure of chatting briefly with co-author Jeff, who shared that a chance meeting with Andrea at a writers’ conference sparked the initial idea for them to pen a book together.

I’m only a few chapters into it, and I have to say it is the best kind of dating advice book — smart, funny and full of common sense advice. Jeff and Andrea play well off each other, especially since they are coming from different vantage points: she’s married, he’s single. One of my favorite quotes so far from Jeff has to do with the question of who pays on a first date:

“The guy who doesn’t pay isn’t some daring, trailblazing pioneer for women’s rights; he’s just cheap.”

Well said.

| Andrea Syrtash, dating advice, dating bloggers, dating rules

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

A New Professional Chapter

September 5th, 2011 — 4:41pm

Readers of this blog know that I’ve been pounding the pavement for awhile now. I’m happy to report that after 30+ interviews over the course of five months, I have landed a job with respected PR agency Evins Communications.

Much like the job search process itself, this happy ending has had a lot of parallels to dating.

Fairy Jobmother: my good friend and soon-to-be colleague Andrea got me the interview at Evins.

The conversation doesn’t feel strictly like an interview: There’s nothing worse on a first date than being interrogated like you’re applying for a job. Though tough questions are to be expected when you are seeking employment, the interview should also allow for some give and take. All 3 of my interviews at Evins were engaging conversations that went much deeper than the standard “where do you see yourself in 5 years?” fare. 

Both parties aren’t waiting to see if something better comes along: When you’re just not that into someone, you can’t help wanting to keep your options open. During my job search, I had multiple companies follow up with me more than once then fail to close the deal. It took just five days for Evins to extend me an offer, a reminder that…

You know when the chemistry is mutual: So many times during the dating process, you try to convince yourself that there’s a spark even when all the indications are otherwise. But you can feel if chemistry truly exists, because it just flows. I had that feeling with each person I met with at Evins.

I can’t wait to work with them when I start my new job on Thursday. Let the new professional chapter begin!

| dating rules, getting a job, job interviews

Dating Rules For Job Interviews: Part One

July 7th, 2011 — 5:54pm

Over the last couple of months, I’ve been pounding the pavement for my next full-time gig. In the course of doing so, it’s occurred to me that many of the rules about first dates also apply to job interviews.

I’ve also found myself thinking that, just as most of the dating advice out there is geared toward women, most interview tips are designed for job seekers. After all, in this tough hiring market, the pressure is on the potential employee to make a good impression, right?


Much like a first date, a job interview is a two-way street, requiring preparation and engagement from both sides. Employers would do well to keep the following dos and don’ts in mind:

Do Your Homework: As a job candidate, I would never show up to an interview without having researched the company first. In this age of the Internet, it doesn’t take long to be prepared — just like it doesn’t take long to scan someone’s resume beforehand. During a second interview with one company, the executive clearly knew nothing about my background, nor did he even know what position I was being interviewed for. An hour later, I received a call from him saying he had spoken with a colleague who clarified things and would likely ask me back for a more focused third conversation — one that would have been unnecessary had this conversation taken place prior to my second interview.

Don’t Be Late:  This seems like an obvious one. Because as a job seeker or date, tardiness usually disqualifies you from being taken seriously and getting to round two. And yet, I’ve been on a handful of interviews that have started more than 20 minutes late — without any apology from the person conducting it or any visible sign that he or she was rushing from a prior appointment.

Do Pay Attention: On a date or an interview, there’s nothing more frustrating than when the person you’re talking to isn’t listening. During a phone interview with the VPO of a popular men’s lifestyle website, he asked a fairly involved question. After giving my three-minute answer, the guy told me–

“Could you repeat what you just said? I was checking my personal email and a friend of mine got engaged — it’s not every day that happens — so I didn’t hear anything you just said.”

I don’t know which was worse. That he admitted to this, or that he said was “too busy” to spell out his email address when I asked him for it so I could follow up. Ugh.

Up next…the most inappropriate job interview tangent ever and worst faux pas when it comes to closing the deal (or not).

| dating rules, job interviews

Rethinking The Rules

February 13th, 2011 — 10:48am

Much as I hate to admit it, I’ve always been a stickler for certain rules when it comes to dating. Having been raised by two strong, smart parents who were madly in love with each other, I’ve inevitably found myself trying to emulate the high romantic standard they set – and to spare myself any needless heartbreak along the way. 

Enter these so-called rules, designed as a self-defense mechanism to gauge whether to take a chance with someone. One of the more traditional (or, I suppose, antiquated depending on your point of view) ones is the notion that, when you first start dating a guy, all of the initiative taking should come from him. 

After all, we’re taught to believe that when a man is interested, that’s what he does. And, in a city like New York where you feel like expressing interest yourself could be the tipping point that turns someone off, you tend to second guess what is really just common sense. Say, for example, picking up the phone. 

Radio silence after a first date usually means there’s no spark. But what does it mean after you’ve been on three amazing and (what feels like) mutually enjoyable dates? According to my wise brother and sister in law, it doesn’t necessarily indicate a loss of interest. It could simply mean that the guy, having demonstrated plenty of initiative, wants (understandably) some reciprocity. 

So, I went out on a limb and gave said guy a call. Surprise, surprise, we managed to pick up right where we left off. And I realized that, instead of standing on ceremony about who calls who, sometimes you just have to bite the bullet and put yourself out there.

 Yep, good old common sense. No better rule to follow than that.

| dating rules

In Defense of Courtship Rituals

February 5th, 2010 — 6:52pm

Earlier this week, I received an email from a male reader with an interesting take on my recent romance with PR exec E.

Based upon my posts about E’s knack for planning elaborate dates, said reader assumed his wining and dining me must have had an ulterior motive – to get me in between the sheets.

As I read his (thankfully) inaccurate take on E’s modus operandi, I couldn’t help thinking how the art of courtship seems to be something increasingly scoffed at in the dating world.

Last year, a conversation with my summer fling during a rare night out found us talking about one of NYC’s five-star restaurants. He asked if previous significant others had taken me there and I said yes.

“Those guys were just trying to impress you,” he said dismissively.

And what, I thought to myself, is so terrible about that? Why is it that, according to the new dating rules, men are often considered foolish for wooing a woman, while women who want and enjoy the experience are made to feel guilty for it?

Over the years, I’ve gone out with men who have taken me out lavishly as as well as those who preferred more low-key courting. Neither approach is wrong, it’s simply — like the type of person you tend to be attracted to — a matter of personal preference.

During my time with E, he planned a series of great dates ranging from nights out on the town to quiet, cozy evenings in the neighborhood. He was thoughtful about everything and, when it comes to the art of courtship, there’s nothing more than romantic.

| being wined and dined, dating rules, the art of courtship

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