Last night, over a glass of Pinot, I was catching up with a friend who couldn’t believe the questions that she was asked on her latest date. Hint guys: How old are you? What are you measurements? Why are you not married? If you didn’t know, these are inappropriate questions.

If information is what you are seeking (which is completely understandable), there is a smooth creative way to get all the information you could possibly ever want. Instead of asking her age, you can easily ask whether your date knows your friend from their college and determine the class year and do the math in your head.

As for weight and measurements, I’m not sure why that is important, there is either an attraction or there is not. If being a size two is a mandatory requirement, I would revisit your non-negotiables list.
And finally, my favorite, “Why are you not married?” First off, people who live in glass houses should not throw stones. The same question taunts any singleton. And really, isn’t the answer obvious? The person wasn’t ready or just hasn’t met “The One.” I told my friend that I was positive this was meant as a compliment, but nonetheless the question is nonsensical to most women.

Making conversation in the beginning of a date can be tough. Sometimes nervousness brings out statements or questions you wish you’d never said or asked, and in a Seinfeldesque manner, you chase to get them back. (That is why I always advise to go on a second date.) Try to pry the answers you’re looking for out via dialogue instead of pointed questions; you’ll get the same information and avoid walking the tight rope of, “to ask or not to ask?”

An old friend reached out to me this week expressing he had always had a crush on me but felt the timing wasn’t right for one reason or another. But now, though normally he would be shy and not express himself, he is trying the “George” (Costanza fictional character from the sitcom Seinfeld) and doing the opposite. For me, I truly applaud this thinking/behavior. Why wouldn’t you say how you feel and what is on your mind?  I get the whole “risk and rejection is not fun” theory.  But, on one hand, you have the status quo which is apparently not where you want to be. Shaking that up by articulating your desires, can only change the scenario for the better (potentially a happily ever after) or, at a minimum, give you the information you need to not waste your time and move forward. That being said, and admittedly this is sexist comment, I’m not sure I would encourage the same forthrightness by my women friends.  Despite the huge strides in the women’s movement, I believe there is a romantic ideal – call me traditional and old fashioned – that men do the pursuing and courting when it comes to romantic relationships. Women should flirt no doubt, but it is my experience that men (and their egos) generally give them enough of a “George” to go after so they aren’t at risk of letting him slip by.

I’m at a Springsteen concert (gotta love the classics) with a dear friend of mine. And the House in Madison Square Garden is getting down. I turn and smile at my friend whosedanceresemblesthe Seinfield Elaine dance. However, he calls it the “Tarantula Dance.”  Now if he reads this, my ass is in trouble. Though he shouldn’t be because he is not single. That aside, the dance was so endearing/adorable, yet funny (when your stomach hurts from laughing, funny). But the best of it, knowing you can be your absolute self in front of someone and not worrying.  A friendship or romantic relationship is at its best when you can be that person and they still think you’re amazing. Not that doing the Elaine or Tarantula Dance can be seen as a fault, but I guess you know when you can be absolutely yourself in a relationship and when someone knows your faults/quirkiness/idiosyncrasies and even finds them endearing, then you’ve got something good.

New York City Singles 2009–The Ultimate Dating Guide from the Dater’s Point of View. As usual, my friend and I were deep in “serious” Seinfeld-esque discussions involving our celebrity lists…Emmanuelle Chriqui, Kate Beckinsale, Denzel Washington…Then we quickly switched gears to what we thought was a brilliant idea. What if there was an imdb or Zagat for dating? All necessary information would be available with feedback and ratings. We could have categories like “Cost” (high/low maintenance/Am Ex Black Card), “Decor” (Carson Kressley HELP!), “Service” (Getting into Harvard is easier) and “Overall Date.” That way before you asked someone out, you’d know prior what to expect. Efficiency at its best.

Imagine the reviews: “Great in its heyday,” “lovely garden,” “neighborhood favorite,” “NYC’s finest hottie,” “kind of, sort of,” “chaotic,” “authentic without extraneous enhancements,” “doesn’t disappoint”, “cheapskate took the phony offer,” “phony offer made,” “ever-changing menu-commitment phopic” and “Per-fect palate awakening.”Of course included in this guide will be those fun adhesive tabs “Love it,” “Must Try,” “Best in Bed,” “Top Pick” and specialty sections “Geographically Desirable,” “Key Newcomers,” “Back on the Market,” and “Brunch Worthy.”

Coming soon…

Correction: There is indeed a Zagat Guide for Dating entitled Zagat Dating and Dumping Guide – one for New York and one for Los Angeles readers! As if that wasn’t enough, there is also a Zagat iPhone application where you can find the best places to go on a date!

With online dating being mainstream these days, it seems a little odd when you discover someone who doesn’t utilize the resource…why wouldn’t you? It is self marketing and you don’t have to lift a finger at the outset.  The tides have turned from where people socialized in bars wondering if the “one” could be there too; and asking friends for set ups…to sitting on the couch clicking away.  As singletons, we have become somewhat lazy. Why go out (if you are exhausted after a long day) when you can have probably a better batting average clicking away?  Regardless if it is online or in-person, the end result is determined by in-person chemistry and in my humble opinion the sooner you meet “live” the better.  The upside is, while clicking you can watch that hysterical Seinfeld rerun in your pjs knowing that most people online are looking for that same elusive “one”.