Wanted: A truly helpful mobile virtual personal assistant

We've been on the brink of a new relationship with our gadgets for years.

"Real soon now," we're told, mobile apps will interrupt us with personalized information we never asked for. These interruptions would show us opportunities ("Those shirts you like are half-off at the store around the corner"), facilitate our social lives ("Your friend Janet is also visiting New York and is free for lunch—would you like to invite her?") and save our bacon ("You haven't ordered a flower delivery for your anniversary—would you like me to take care of it?").

What are they waiting for?

Apple's Siri responds impressively but doesn't take the initiative to interrupt much.

MindMeld is supposed to ship to general availability an app that churns out information related to your video conversations. The technology and platform look impressive, but the purpose of MindMeld's proof-of-concept app will be context for conversations, not mobile personal assistance.

EasilyDo is supposed to give you predictive results, but like most in this category, you have to work for it. The results are a fraction of what you want, actually harvesting data from social networks, calendars and location-oriented databases and placing them in a stream.

EasilyDo performs a wide variety of useful tasks like contacting people for you, telling you when to leave for your meeting, getting directions, automatically creating new contacts and many other things. EasilyDo automates tasks to simulate a personal assistant, but it doesn't do anything you haven't specifically commanded it to do. It doesn't interrupt you proactively with contextual information beyond things like telling you to leave for your next meeting.

Osito is another cool app that suffers from the same lack of creative interruption as EasilyDo. It's more of a rollup of the kinds of information you can get elsewhere, but presented in a stream with some pop-ups. It's more about automation than contextual assistance.

Foursquare just got interesting. The company rolled out a test version of Foursquare that throws advice and context at you when you walk into a restaurant or around a neighborhood. ("Try the cheese fries in this place—they're incredible.")

Checking in isn't required. In fact, the information will pop up even if the Foursquare app isn't running. Now that's what I'm talking about.

Sadly, the test is for 2000 lucky Android users only, with a wider rollout promised for an unspecified future. Foursquare tested a comparable feature called "Radar" two years ago, but killed it after "Radar" killed battery life.

Google Now has by far the best proactive interruption in the business, if you have an Android device.

Google Now grabs information about you from Gmail, Google Search, and elsewhere, and uses that data to improve results.

Lately, Google has folded in some amazing capabilities. For example, it preemptively feeds you information about your car rentals, public transportation information based on guesses about where you might want to go, movie tickets and sports scores.

Google Now tells you more information about whatever's on screen. It knows what you're watching because, with your permission, it listens to the sound of the show to figure out what you're watching.

Google Now is great in every way except one—it doesn't give you enough information. Leaving Google Now running gives you a mostly static view, with "cards" coming in very infrequently.

Field Trip, another Google product, is wonderful only because of what it promises, not what it delivers.

We learned recently that Field Trip was originally designed for Google Glass but shipped on the iPhone while Glass was still in early development. It's now available on Glass.

Field Trip has the right idea, popping up contextual data. However, these are based on a list of arbitrary database-oriented websites, such as "Historic Detroit," "Public Art Archive," and "San Francisco Architectural Heritage." Unless you're in a major city, Field Trip contextual information is slim pickin's.

There are other services that claim to interrupt with contextual information. But in my experience these require launching the app and refreshing it—a conscious choice followed by deliberate action, which is the opposite of what's promised in this category—interruption.

Looking at these few examples, the industry overall seems hesitant, unwilling or (most likely) unable to meet the promise of interruption for contextual information.

It's true that this category is fraught with hazard. People feel their privacy is being violated when a gadget demonstrates what it knows about them. It's an irrational concern because not letting the user take full advantage of harvested data (as is the case today for most users) doesn't equal privacy, just ignorance.

Users might get overwhelmed by too much interruption data. But there are better ways to stop overload than simply withholding messages. Let it be turned up gradually. Offer a snooze feature. Set times of day. Notify only when moving.

The ideal service would combine the benefits of Foursquare, Google Now and Field Trip. It would give you useful and interesting data not just for general areas or historic landmarks, but down to the specific address level.

It would be like the test version of Foursquare, interrupting you whether the app is running or not.

It would be like Google Now with its uncanny ability to know all about you and learn from your actions.

It would be like Field Trip in bringing in disparate human-curated databases to augment your reality.

Most of all, I would like these services to turn up the fire hose. Limiting access to a handful of users like Foursquare, dribbling out frustrating little bits of data like Google Now, and limiting information sources to a handful of content sources like Field Trip isn't going to cut it.

This category has been full of promise and potential for two years now. The wearable computing category is exploding with activity. It's time for the industry to get over its shyness and start interrupting us with more and better personalized contextual information.

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Staycation, all the apps I ever wanted

Labor Day is the greatest weekend of the year—the entire point of the holiday is to have an extra day to take it easy. And while the airports and highways will be jammed with people trying to squeeze in one last trip of the summer, to truly take it easy you don’t have to go far from home. It’s time for a good old-fashioned staycation. These apps can make sure you have a great one without sweating too much over the planning.

Field Trip has the scoop on all the good eats close by.

Whether you’re at home or on the road, you gotta eat. To spice up your staycation, try to find new-to-you places instead of your normal haunts. These apps make it easy as pie—pie you didn’t cook yourself.

While Field Trip (free for iOS and Android) is absolutely perfect for exploring a new city, it can also help you find cool places in your hometown, spots you might not otherwise know existed. From Google’s Niantic Labs, makers of Ingress, Field Trip uses your GPS location and a robust database of sources (from Scoutmob to local blogs) to “surface” nearby places by buzzing your phone with information about the things you pass by, everything from out-of-the-way restaurants to public art.

We had mixed feelings about Field Trip's iOS version, but the Android version is (understandably) better implemented, with the results hitting your home screen as Google Now-style cards. If you are among the fraction of the 1 percent who has Google Glass, a heads-up version of Field Trip is even available, like a virtual tour guide on your face.

Savored's discounts are the perfect excuse to try a new restaurant.

Savored, a free app for iOS and Android could use a facelift—it’s got that skeuomorphic black leather texture with fake stitching across the top, and while it was updated in January 2013 it still isn’t optimized for the iPhone 5. But like a truly great app, it does one thing, and does it well. Savored lets you book reservations—anywhere from tonight to a month out—at fancy restaurants in 10 major cities, and score a discount on your bill at the same time, from 20 to 40 percent.

When you arrive just let the restaurant’s staff know you booked through Savored, and they’ll apply your discount. Unlike dollar-based deals like Groupon and Restaurants.com gift certificates, Savored’s percentage off doesn’t lock you into spending a certain amount—you can splurge on cocktails and dessert or split an appetizer and call it a night. You can search by neighborhood, see results in a list or on a map, and check out a review of each restaurant and its menu, too.

Panna's videos feature celebrity chefs showing you how to cook tasty new treats.

Still hungry? On a real vacation you might be forced to dine out, but on a staycation it’s optional. If you don’t feel like putting on pants just because restaurants require it, turn to a delivery specialist like Eat24 or Seamless. Better yet, grab a new cooking app and make the fanciest thing you can find, something you’d never take the time to do otherwise. Panna (free for iOS) features recipes by famous chefs like Rick Bayless and Anita Lo, with gorgeous videos to walk you through everything. It’s a gorgeous interactive magazine, so you get one free issue with 7 recipes; a bimonthly subscription is $14.99 a year, and back issues are available as in-app purchases too.

LivingSocial knows all the haps around town.

When I was a kid and we’d whine to our mom that there was noooothing to do-ooo-ooo, she’d holler back, “Read a book!” Today’s moms could just as easily say, “Check the LivingSocial app!” Because while you won’t find literature inside, LivingSocial (free for iOS, Android, and Windows Phone) does have a huge range of deals around your city, including tons of activities. Two whole minutes of browsing the things to do category turned up everything from spa packages to flying lessons to horseback riding to beer tasting to movie passes to half-priced skee-ball at Dave & Buster’s. It’s easy to browse, buy, and share deals from right within the app, and you don’t need to bother printing anything either. You’re sure to find something cool to do that won’t break the bank.

Besides integrating your Google Calendar, Outlook calendar, and Facebook events in one attractive and free iOS and Android app, UpTo features hundreds of niche calendars you can subscribe to, like the schedules for your favorite sports teams and upcoming shows at your favorite concert venues.

UpTo lets you sniff out events and seamlessly add them to your calendar.

Look in UpTo's local section for some intriguing ideas for must-do activities in your area—although these calendars can be a little hit or miss. For example, we found San Francisco Family, but it’s sponsored by Ticketmaster and only had two events. On the other hand, San Francisco Art Events was chock-full of gallery openings where you can check out incredible works of art—and hopefully fill up on wine and cheese. UpTo also it makes it easy to alert your friends to stuff it’d be fun to do together. You can have a friends list of UpTo users, or just rely on tried-and-true Facebook, Twitter, and email sharing.

Another app for finding stuff to do, Eventbrite (free for iOS and Android) has some cool categories like Festivals and Outdoors, and it can narrow down results to just this weekend. You can buy tickets to things in the app (some can even be sent to iOS’s Passbook feature), and some events are even discounted. Heck yeah I want to save 30 percent on a ticket to the San Jose Bacon Festival!

Still standing? Gravy (free for iOS and Android) lets you search for events based on your mood. Red Rover (free for iOS) specializes in family-friendly fare in San Francisco, New York and the Hamptons, Boston, and Atlanta, and even suggests nearby things to do before and after. And Groupon (with free apps for iOS, Android, and Windows Phone) is still the granddaddy of daily deal apps, but as with LivingSocial, if you find a new favorite spot, make sure to go back and patronize them again at full price someday!

Applauze is your ticket to...buying tickets.

Sure, it's fun to travel for a big concert, but once the music starts playing, if it's good, you’ll forget what city you’re in anyway. So you might as well see some bands in your own backyard. As long as you have a safe ride home, go ahead and cut loose—after all, you’re not working tomorrow.

Applauze (free for iOS) has listings for concerts, sports, theater, and community events all around you, and lets you buy tickets without leaving the app. Its slick design features a big, beautiful image for each event, and the green ticket icon gives the price you’ll actually pay, fees included.

Flip Applauze's category ring to Community to zero in on events more likely to be free, including street fairs, films, and lectures. You can even invite friends via Facebook, SMS, or email, and you both get $5 in credit for the referral. It’s currently in 41 cities, and you can preview the selection online.

Timbre plays musical samples of all the bands coming to town.

If you’ve ever checked out your local concert listings, and thought, “Geez, I’ve never heard of any of these people,” don’t automatically assume it's because you're old and lame. (You're totally not.) Just grab Timbre (free for iOS and Android), and as you scroll through its list of upcoming shows in your area, tap a name for more details—including a preview of that band’s music, and of course, the opportunity to buy more of it from iTunes. Genius!

Still dancing? BandsInTown (free for iOS and Android) can scan your music library and let you know when your favorites are coming to town, or recommend local shows you might like based on your taste. And Thrillcall (free for iOS and Android) specializes in last-minute tickets, but it’s currently limited to San Francisco, New York, Chicago, and Seattle, with more cities on the way.

We can do better than this, thanks to Priceline's Name Your Own Price feature.

Starched white bed linens, tiny bars of soap, a Do Not Disturb sign for the doorknob, and of course maid service: Staying in a hotel is awesome, even in your own city. But you shouldn’t pay an arm and a leg, especially when you could be sleeping in your own bed for free.

It’s not the newest, trendiest hotel app out there, but Priceline (free for iOS, Android, and Windows Phone) is easy to use, and its signature name-your-own-price feature is ideal for in-town stays. Go ahead, put in a ridiculously low bid—$99 for a 4-star hotel in Santa Monica!—because the stakes are low too. If you don’t get any takers, you can always just go home.

First, pick your city and dates; you can even check in tonight. Then tap the sort button in the upper-right to isolate four-star and higher hotels and optionally pick your desired neighborhood—staycation is time to splurge, so save the 2-star motels for your next road-trip stopover. Use the Browse All Hotels tab to get a sense of what the hotels want you to pay, then pop over to the Name Your Own Price tab. Here you’ll pick a neighborhood and a star level, and decide how much you want to bid.

HotelTonight's deals are so last-minute they're not even available until noon on the same day.

Now, if your bid is accepted by a hotel fitting your criteria, you can’t change or cancel the reservation, and your credit card is charged right away. But it’s safe to go really low, say, 50 percent of the quoted “average” rate, because if no hotels take your offer, you can try again with a different neighborhood or star level. To try the same request again you’ll have to wait 24 hours. I’ve had great luck reserving same-night rooms for rock-bottom prices, once nabbing that $99 4-star Santa Monica room from a beach chair while I watched the sun sink into the Pacific. Not bad. The new Express Deals feature also has decent discounts, but you get to pick a specific hotel rather than bidding on anything you can get.

Still awake? If Priceline doesn’t come through, or you just can’t stomach the thought of committing to a reservation without knowing exactly what hotel you’re staying at, try HotelTonight (free for iOS and Android). It also specializes in last-minute deals, helping hotels fill their empty rooms, but you get to see where you’ll be staying before you book.

Yeah, I think AllTrails has a few hikes for us to try.

Going for a hike can really make you feel like you’ve gotten away from it all, and sticking your feet in a lake or river is the best way to recharge. Get out there—you might not have go as far as you think.

AllTrails (free for iOS and Android) can help you find tons of places for hiking, mountain biking, and trail running, all rated by the community and marked with difficulty levels, distance, and approximate time. Sign up for an account to keep a list of the trails you’ve bagged, write reviews, add photos, and share them with friends.

If hiking sounds suspiciously like exercise, don’t forget that lazing around on a picnic blanket reading a book counts as being outside too. If you need something new to read, Goodreads can recommend new books and let you know what your friends are enjoying—just amble down to the library or bookstore and fire up Goodreads' free iOS or Android app.

Indulge your inner comic geek with Marvel Unlimited. Just try to do it outside—even superheroes need their vitamin D.

A Marvel Unlimited subscription is only $10 a month if you want to spend the whole weekend discovering new comics or revisiting your favorites. For the price of a ticket to the latest superhero movie, you could read the same characters’ entire stories. The app (free for iOS and Android) even have plenty of free issues to whet your whistle.

Still going strong? You could blow an afternoon geocaching—that’s using your phone’s GPS to search for hidden treasures left behind by other geocachers—and the free Geocaching app for Android and iOS makes it easy to get started even if you’ve never tried it before. Once it gets dark, Star Walk ($3 for iPhone and iPad) uses augmented reality to overlay stars, planets, and constellations over the night sky. It'll make the same old sky over your same old house look downright magical.

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