Category: dating dos and don’ts


The Good And Bad of Texting

June 22nd, 2014 — 11:17am

People_textingI’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 S, 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.

| dating dos and don'ts, online dating, text messaging

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

When Raunch Replaces Romance

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.

| dating dos and don'ts, first date ettiquette, online dating

It Really Is All About Luck And Timing

June 23rd, 2013 — 12:40pm

love-o-clockWhen it comes to finding love, you often hear about the dual forces of luck and timing. In navigating the ups and downs of thirtysomething singlehood, you inevitably find yourself questioning whether this duo is working in your favor. Lately, I’ve experienced examples that they are – in very unexpected ways.

Case in point number one – my derailed reunion with D, an out of town bachelor I met during my Great Dating Blitz three years ago. After reconnecting back in April, D and I began communicating almost daily. Soon, we were planning a romantic weekend for him to visit. But the Friday that D was to arrive, his flight ended up getting cancelled because of torrential rains.

Suitcase packed, D headed to the airport anyway, attempting to fly standby. Several hours later, he was informed there would be no availability until the following afternoon. We spoke and texted our mutual disappointment, initially talking about the possibility of rescheduling.

That conversation has slowly tapered off. I can’t help wondering, was Mother Nature’s intervention intended to spare us both from a protracted long distance scenario?

Meanwhile, closer to home, two great dates with a guy I met at speed dating were followed by him cancelling last minute without an explanation. Though my instincts said I should say sayonara because he was clearly not that interested, I opted to give Mr. MIA one more chance. After all, in this post-modern dating world, etiquette about making plans is a more fluid thing, right? We’re supposed to be flexible, etc., etc.

Not so much – as I was just reminded by an old flame. When work forced him to cancel our plans, he called (rather than texted), offered a heartfelt apology and immediately rescheduled. His thoughtfulness confirmed what I already knew about Mr. MIA: he’s not a candidate for anything serious.

Bottom line, it seems that luck and timing have been doing their part to steer me away from men with whom there is no future. All the more reason to be hopeful about stumbling upon the right guy — with their capable help of course.

| dating dos and don'ts, dating in your thirties, old flames, speed dating, The Great Dating Blitz

New Book And Giveaway: The Gaggle Approach To Dating

June 18th, 2012 — 7:14pm

It’s a question all of us single gals have asked at one time or another — where are all the single, available men? Well, what if your existing social circle held the answer to that question? This is the premise of (Simon & Schuster), a new book by Jessica Massa, co-creator of the acclaimed website WTF Is Up With My Love Life?!

Based on in-depth interviews with young women and men across the U.S., the book is a how-to guide for navigating your love life in what Massa describes as a “post-dating world.” It talks a lot about how technology has changed the dating landscape – and how the Gaggle concept can help women take charge of their romantic fate.

So what exactly is the gaggle? Massa and her best-friend-turned-business-partner Rebecca Wiegand coined the term to describe the collection of guys in every woman’s life.

“Your gaggle is the group of guys in your life who you might not be “dating,” but who play different roles, fulfill different needs, and help you to figure out who you are and what kind of guy and relationship you ultimately want,” says Massa. “These guys are all around you, once you open your eyes to them! There are ten types of guys who might be in your gaggle at any moment (for a list of all ten types).”

Massa adds that the gaggle approach is easy to adopt – it’s simply a matter of shifting how you think about the men you know, and the new men you’re meeting every day.

“Women don’t need to learn any tricks or memorize any rules,” she says. “They just need to start recognizing that all the ambiguous, not-quite-romantic-but-not-quite-platonic relationships that they have with men mean something.”

You can read an excerpt of The Gaggle . Even better, I’ve got a copy to give away to one lucky Single Gal In The City reader! Post a comment below by Friday June 22nd and tell me what you think about the Gaggle concept, and you’ll be automatically entered to win!

| dating advice, dating bloggers, dating dos and don'ts

Singles Event Pick: Mindful Dating Workshop

May 14th, 2012 — 1:59pm

Dating in NYC (or anywhere, for that matter) can be exhausting at times. If you’re looking to inject new energy into your love life, you might want to check out Mindful Dating.

Unlike many “how to meet your mate” workshops, this one will take the form of a fun and interactive Sunday afternoon brunch that includes wine, cupcakes and light fare. Makeup artists will be on hand to demonstrate how to showcase your best physical assets, and the event features presentations from licensed psychotherapist Chamin Ajjan, registered dietitian A. Fiorella DiCarlo and Dating Coach Trenia Parham, MS.

Mindful Dating will take place on Sunday, June 10, 2012 from noon-4pm at Silk Studio in Noho. Tuition is $75 and includes brunch, make-up demos, and presentations. To sign up, click here or call Chamin at 917.476.9381.

| dating advice, dating coaches, dating dos and don'ts, singles events

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

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

The Problem With Expecting Too Little

August 7th, 2011 — 4:39pm

When it comes to being a single thirtysomething woman, much has been said and written about having expectations that are too high. A recent conversation with a good friend found me wondering if just the opposite is true – are we becoming too permissive of bad behavior?

We live in a day and age where multi-tasking is the norm and having someone’s undivided attention is the exception rather than the rule. Not surprisingly, this has carried over to the dating realm too. My aforementioned galpal recently started seeing an attentive guy with whom she’s made the gradual transition from friends to something more.

“I can’t believe it – he never texts other people when we’re out together,” she told me with a mixture of shock and delight.

As she said this, it occurred to me this used to be the norm – and that there’s nothing wrong with still wanting or expecting it to be. 

For as much as we’re primed to believe otherwise, there are still people out there who believe in good manners and etiquette. I was happily reminded of this during a recent exchange with Long Island native Harrison.

My aunt and his mother thought Harrison and I could be a match. Within hours of emailing his mother, I received a thoughtful, engaging email from Harrison inviting me to call him. We talked for about a half an hour and he said he would be in touch. No endless back and forth (as is all too common in the online dating world) or phone tag – just swift, respectful communication that didn’t waste either of our time.

Behaving like a gentleman and acting like a lady are only outdated standards if we allow them to be.

| dating dos and don'ts

Dating Wisdom From The Twitterverse

July 26th, 2011 — 1:52pm


Now matter how much experience you have (or like to think you have) with dating, sometimes you need a little expert advice. The other day, I turned to the twitterverse for their take on a bachelor’s pre-date actions.

Said bachelor — we’ll call him Mr. Shadowy — and I had gone out a few times a few months ago. Both were drinks-only dates, both ended with kisses goodnight. Mr. Shadowy travels often for business and texted twice from his recent travels. After about a month of radio silence, he unexpectedly resurfaced on Friday with a text message inviting me to drinks and/or a movie.

“We should catch up!!” he exclaimed.

My initial thought was to say no thanks given the lengthy absence of any communication. But, as part of my ongoing attempt to be less jaded and more open minded, I figured, why not? We left it that Mr. Shadowy would call to confirm time and place for date #3 on Monday.

Sure enough, he did get in touch — on Monday via text, at 6:15pm, to suggest drinks. Call me high maintenance, but I think it’s a little inconsiderate to wait until this late in the day to confirm, and then not really have come up with anything concrete in the way of plans. My gut was telling me that Mr. Shadowy was making me his back up plan and/or didn’t care enough to put any thought whatsoever into our date. Either way, I was inclined to cancel. First, though, I decided to do a little informal poll on Twitter.

“Unless they’re KILLER plans (i.e. great seats to Book of Mormon thanks to a lottery),” said relationships guru @DatingRev. “It’s a major fail.”

Added dating coach @RachelTRusso—

“More likely to stay married to his/her career than to you!! I’d just say no and reschedule or scratch it!”

Several tweeps confirmed my suspicions that Mr. Shadowy was either waiting for something (or someone) better to come along, and more than a few said this is standard male behavior.

“Annoying, but happens all the time,” said @SingleGirlie. “Think it’s a guy thing.”

Now married, @DatingRev wasn’t letting his gender off the hook so easily.

“It’s a boy thing – not a man thing. I planned 3-5 days in advance, and confirmed the plans 1-2 days before.”

I couldn’t agree with him more. I’ve been lucky that almost all of the men I’ve ever dated, casual or otherwise, were respectful enough to make and confirm plans much further in advance than two hours before. Which is why, once my gut check was confirmed, I happily told Mr. Shadowy – via text, of course — date #3 was off.

| dating coaches, dating dos and don'ts, Twitter

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