As a parent you don't always see the hard questions coming. When planning the vacation day trip into San Francisco's Haight-Ashbury district, who knew I would have to explain the architecture of a bong to my sweet 16-year-old daughter? In retrospect, of course, any Dad with half a brain would anticipate the countless head shops on Haight. Just consider all those upscale baby boomer tourists who need their pot pipe straight from psychedelic head quarters. I didn't bring that half of my brain on this trip, apparently.

I wasn't entirely convinced of her innocence, either, but proving her naiveté on all weed-related matters seemed to be part of the game. "No really, Dad, I know nothing about this. I PROMISE.... . You know I don't do any of that stuff....Oh, look a double-barreled hookah...and Job papers." My fiancée, my daughter's future stepmother, was having way too much fun watching me squirm -- until I realized finally I was being played by both of them. This is one time when steering them into the high-priced boutiques was the safer strategy. Middle-aged Dads learned long ago that sometimes you just have to buy your way out of a problem.

These are the moments when it is good to pack a lot of mobile technology. While the ladies tred on tie-dyed everything, I got to test out a bunch of new toys that glimpse a more powerful mobile future. I spent a lot of time using the iPhone 3G's GPS capabilities to track our movements throughout the city and geo-tag pictures. On bus rides, my fiancée kept urging me to put the "damned thing" away. "Damned thing" is her nickname now for the iPhone. "If you say 'tax deduction' one more time in connection with that damned thing, I am throwing you off this bus,: she rants. "And keep your eye on your daughter, please. I think that schizoid in the stained raincoat is trying to hit on her."

All the bad stories you have been hearing about the new iPhone's dodgy GPS and 3G reception are pretty much true in my experience. Geo-location often relies more on the old system of triangulating cell and WiFi signal strength than it does on precisely pinning you with the GPS chip. Try waving it in the air and yelling to the satellite until it notices you. "Can you see me now?" In practice, the distinction is moot for now, because things like proximity searches and even geo-tagging of images get close enough. How Apple or third parties layer more discriminating services on top of such a weak geo system is anyone's guess. I wouldn't trust this GPS with turn-by-turn navigation. The first VZ Navigator phone I reviewed from Verizon two summers ago was infinitely better. 3G signals pop in and out arbitrarily, and you often need to shut down the phone or toggle the 3G setting to retrieve the purported broadband signal. I think the online groundswell of dissatisfaction is going to poke through Apples Teflon brand image any day now.

When it works, geo-located, map-based search will be ungodly powerful. The local search hurdles that restrain online and even current mobile search start to disappear when a map interface lets you run a proximity search for people and services in a selectable radius. The big difference from previous searches is its frictionless nature. You don't need to know your zip code (which may be too wide anyway). The map is such a clear and natural interface that it quickly becomes a reflex. Combine this with detailed local listings, and then even street level imagery and turn by turn directions, and you are onto something usable and lucrative. Google's Eric Schmidt got blasted by critics the other day for suggesting his company ultimately would make more money from mobile than the Web. I don't know if his numbers add up, but I am sure this is the kind of product and targeting potential he has in mind.

Forget that silly nightmare scenario of nearby shops besieging your phone with Bluetooth-enabled coupons and come-ons. There are many less intrusive ways to leverage location. How much would Starbucks or Borders or FYE pay to have their logo drop down onto the results map off of their respective keywords instead of a nondescript red pin? There is so much possible information I needed or wanted to know based on my location on this trip that any marketer would or should love to underwrite. I am in the panhandle of Golden Gate Park, where much of the Summer of Love camped out, and there is barely a hint of information here. How about letting me rifle through historic images taken at a precise spot in one of the most photographed areas of '60s America? I know where I am on Haight, and where I need to get to back in Union Square, but what bus route gets me there? Why can't that route map drop onto my phone map?

"Do something useful with that damned thing," I hear in my ear. "Your daughter found a printed T-shirt she loves but I think we can find it cheaper somewhere else. Look for more clothing stores here." Anticipating something festooned with spiral-rolled joints and marijuana leaves, I am ready to claim the "damned iPhone can't find a signal...sorry, too expensive." "Look, Dad. It's perfect. 'I am Already Against the Next War.'"

Hmm. Even without GPS, and through all the consumerist-hippie nostalgia, she managed to locate the heart of Haight.

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