Say what you want about The New York Times – that their website sucks, they they have a tendency to victimize and scare the crap out of single women, that they totally misunderstand the Millennial generation and wrongfully pick lazy, privileged, upper-middle class slackers to represent us as a whole (don’t even get me started on that one) – but DAMN, people read it.

Over the past few days, Becky and I have happily been inundated with emails from our fabulous readers about the Times’s latest foray into modern dating and relationships – their Sunday Styles cover story, The Ritual of the First Date, Circa 2010.  And almost everyone had pretty much the same reaction: I can’t figure out if this is cool?  Or creepy?  Should I be into this or not?

It’s a good question, and I’m still sorting out my thoughts as well.  The article centers around a new-ish online dating site called HowAboutWe.com, where user profiles focus less on typical categories like “interests” and “what you’re looking for” and instead ask people to show their personalities by coming up with quirky date suggestions that begin with “How about we…”  So for example, if you want to depict yourself to potential mates as a Phish fan, you’ll forgo the usual “I love music, especially Phish!” and go with, “How about we smoke some weed and dance around to our favorite Phish albums in my backyard?”  Interesting, right?

HowAboutWe.com claims that it “is about putting the date back in dating.”  Well, kudos to the founders – two 31-year-old single guys – for realizing that “the date” is missing in dating!  I couldn’t agree more.  However. In the absence of a governmental decree or a mainstream school of thought telling you to do otherwise, people presumably stopped asking each other out on dates for a reason.  Maybe because they felt that dates were awkward and disingenuous , or maybe because they weren’t leading people to the relationships of their dreams, or maybe because it’s easier on the ego to send an ambiguous text message.  And yes, thanks to that recent romantic shift, we’re all confused as hell.  But is the solution really to take a step back and promote traditional dating, encouraging single people to again meet up with strangers for explicitly romantic one-on-one outings?  Or should we be looking ahead and trying to figure out what’s next on the romantic horizon, and what works best for our unique generation?  Even if that’s a structure comprised of ambiguous-but-natural Non-Dates and dah guys? To me, something about the ‘back to the future’ solution seems like a surface level band-aid cure.

So while I applaud anyone who is taking an optimistic, proactive approach to the post-dating world, I’m having trouble getting past the feeling that this concept of getting to know people by getting to know what kind of ‘dates’ they’d want to go on is sort of…gimmicky and outdated.  It seems to be the opposite of the organic, idiosyncratic approach to love and relationships that our generation has been exploring. Our parents – the baby boomers – didn’t always get it right (anyone have an update on that stellar divorce rate?).  So shouldn’t we try to embrace a new age of romance and get excited about the new path to relationships that we’ve been forging?

It’d be easier for me to support the dating argument if so many of the date suggestions featured on HowAboutWe.com weren’t so, well, weird.  Don’t get me wrong, a major reason that I live in NYC is that I like variety and adventure and always having the option of doing cool stuff that I wouldn’t necessarily be able to do in, say, my suburban hometown or a more homogeneous setting. But “How about we go to a library or bookstore and leave notes inside books?”  Or “How about we go to a free marriage counseling session with a priest knowing nothing other than each others names?” As Gawker noted, “…the first dates in the Times article read like deleted scenes from Amelie.” It’s no small miracle that Gawker and I agree on this – remember when their sister site Jezebel called us superficial and we yelled back at them? (and picked up quite a few readers in the process – thanks guys!)  But even they seemed concerned that, “…first dates are getting worse! They’re getting quirkier….the 2010, New First Dater, must excruciatingly craft an evening which embodies their own uniqueness.”  No pressure or anything.  I’m sure that’s the real you, planning that mega-date.

Of course, fun and unexpected experiences are a vital part of any burgeoning relationship. But at the end of the day, they’re not necessarily what true connection is built on. Connection is built on personality, and values, and hopes and dreams and goals, and an inexplicable spark that makes you unable to stop looking at each other and touching each other and smiling uncontrollably when that person posts on your Facebook wall.  So why all the razzle dazzle of  “How about we check out Ninja New York, a Japanese restaurant with ninjas for waiters in the meatpacking district?”  Sure, someone’s suggestion to “recreate ‘Ferris Bueller’s Day Off’” shows that they have a sense of humor, which is a step in the right direction.  But then you actually have to do that weird thing, and with someone who you’ve never met before.

I’ve done plenty of fun, ridiculous things with guys, but my most memorable and romantic moments tend to revolve around staying up all night talking, or taking an impromptu walk that lasts for hours, or feeling the butterflies explode in my stomach when I’m kissing someone who I truly care about.  The best crazy moments usually aren’t planned and put into a calendar.  They just…happen when the mood strikes.  And I like to think that, even when life has its boring moments, you can enjoy each other’s company without resorting to “Let’s go walk the High Line and look for people with mullets.”  But all that would make me look so boring on HowAboutWe.com!  I’d lose to “How about we learn how to read tarot cards (after buying a set somewhere in Manhattan) and practice at the 169 Bar?” every time.

I’m curious to see whether HowAboutWe.com, and the inevitably similar ventures that will pop up, will truly help to cure the romantic frustrations of our date-less generation or simply keep us all busy while we wonder why that guy in our dah hasn’t texted us back yet.  The key for many of us may be to embark on these official dating adventures – both traditional and outlandish – with the awareness that, in this post-dating world, the time that we spend not on dates is just as important to the success of our romantic futures.  Most of the guys in your dah will still be around, whether you’re going on the most inventive dates in the history of the world with them or not.  What’s more, the guys in your dah are not going to disappear just because you logged out of your dating profile.  Love in the post-dating world is multifaceted, and that Friend-Non-Date where you spontaneously spent all afternoon jumping through city fountains in the 100 degree weather was awesome, by whatever name you call it, and whether you planned it in advance or not.

But in the meantime…how about we sit in front of my laptop together and watch a bunch of gay guys dance to California Gurls?