East Side West Side, My Side Your Side, Upside Downside

Manhattan is an island slightly under 23 miles in area and 2.3 miles at its widest (near 14th Street). Most people in the rest of the country would think nothing of traveling this distance to pay a quick visit to a friend or to go to their favorite manicurist, masseuse, hair stylist, barber, and so on. But as New Yorkers know, we are not like the rest of the country and even walking an extra five blocks to go to a better dry cleaner will often be five blocks too many. In regard to dating in NY, the choice of venue for planning your rendezvous requires the consideration of not just eating preferences, cost and ambiance but also the very real question of how much cabbing it/subway riding (read: inconvenience) is this person worth?

Clearly, the answer to this question can be very circumstantial so let's start off with making a few distinctions. There is a difference, naturally, between setting up a venue for a date where the parties have actually met before (and thus have a certain level of excitement) and the online dating "date" where you are carefully planning your "means of retreat" (see previous blog on the hierarchy of dating days for more on this). Also, as per previous blogs, we are assuming that the first date even when the parties have met before is on a weekday night and not on one of the coveted Friday or Saturday nights. Certainly, the desire to trek to Tribeca from midtown after work is significantly less than it would be coming from home on a relaxing Saturday. OK, so a weekend night first date would certainly impact the equation. Lastly, we are again talking about first dates here. Not second dates or tenth dates - just that ever scrutinized first one.

OK, now that we have all of these clarifications out of the way, what is the protocol you might ask? Let's start with an example based in the online dating world. Someone you have never met before is asking you to meet him or her near his or her apartment in Battery Park and you live on the UES. The clear response is "Are you kidding me?!!" OK, maybe that's not the response but it's definitely the thought. The understood protocol for online dating is someplace halfway between the two of your offices or apartments. Unless the guy wants to travel to the woman's neighborhood ... Yes, there is still a double standard if you want to call it that. But women, you should not be traveling to his part of town -- and any guy who makes that request from the get-go should be an automatic delete on your "hotlist." Chalk it up to his being clueless or not chivalrous or self-centered or lazy or whatever you would like but the message being sent is NOT a good one. Trust me on this, this is a red flag of huge dimensions.

Even if the scenario is where a mutual friend sets you up, the same rules apply to the "sight unseen request to travel to his hood" code. I know a girl, let's call her Jane (yes, it's an original one) who explained to me how she drove from the city to NJ to meet a guy for the first time because he was uncomfortable in Manhattan. I could probably stop there as I am sure you see what's coming. He was as weird as he sounds and she drove all the way out to NJ for him ... she was commuting on her first date! Clearly, had he come into the city her means of retreat would have been far easier. Ladies, you should not be driving anywhere on a first date. Period. And men, asking this is not going to make a good impression.

But what about setting up the date when the parties have previously met? Really, the rules of etiquette are not all that dissimilar. Most women have had men offer to come by their apartments to pick them up on the way to the first date - even when the guy lives close to the venue and the women live across town. Men, just so you know, I don't think that is the expectation among most women but when men offer to do so it definitely stands out and it usually sends a much appreciated message about the level of interest and consideration.

The expectation is, however, that on this first date the guy will pick a restaurant/bar/lounge/you name the appropriate locale that is convenient for the woman or he will at least ask something to the effect of "hey, would like you to try this great spot on the west side or do you just want to stay local?" This is the sign of a considerate date who is actually excited for the dinner, wants to make a good impression and wants to ensure a second date ... or at least someone who knows the rules of engagement.

So what message is being sent when the subject "asker" (sight seen this time) picks a venue in his neighborhood without even proposing one in the neighborhood of his prospective date?* 9 out of 10 matchmakers (or moms or friends or therapists) would still say that the signs are clear - it's all about him. And it always will be. Of course, there could be a very good reason for the selection - perhaps it's a completely unique, romantic, amazing restaurant that he is sure you will love. But this should be said up front so that the woman can understand there is a specific reason for the 12.6 mile travel.

Of course, when the request for first date travel is to try out some fantastic, new, always booked, gastronomic paradise that you have been dying to go to, that's a definite upside to the request to hike uptown, downtown, crosstown and maybe even to one of the outer boroughs if the Best of Citysearch says it's worth the trip ... OK, that might be second date travel ...

*We all recognize that the guy is usually the one picking the restaurant or bar for the first date. There are many reasons for this which can be addressed in a separate blog. For now, we shall just stick with the understanding that this is the dynamic.