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Why planning ahead is dead

An expanding collection of apps and services will get you what you need right now.

photographs from Shutterstock, Globe staff photo-illustration

I’ve never been a planner — I don’t even keep a calendar, digital or otherwise. And make restaurant reservations? Are you kidding? How on earth should I know what I’ll want to eat in six days — or even six hours? I’m not a fortuneteller, for Pete’s sake.

This is partly because I’m hopelessly disorganized and commitment-wary. But I’m also a relentless optimist. I enjoy the thrill of winging it, and I believe things will usually work out OK — emphasis on usually. Living on a whim demands a certain temperament and the understanding that you’ll win some . . . and you’ll lose some.


Here’s a win: I scored tickets to Game 4 of the 2004 American League Championship Series — the historic one with Dave Roberts’s steal and David Ortiz’s 12th-inning walk-off home run — for under face value, simply because I went down to Fenway that drizzly Sunday night. But that same year, while touring the West Coast, I pulled into Santa Cruz, California, without a hotel reservation . . . and I was forced to spend the night in my economy-sized rental car in a Denny’s parking lot because every last place was booked.

These are the highs and lows of the last-minute life. At least, they used to be. Now dozens of apps and on-demand services exist to mitigate the consequences of such haphazard planning.

Had my sad little 2004 flip phone been able to summon HotelTonight, a magical last-minute lodging app, I likely could have upgraded my Nissan Sentra Suite in Santa Cruz. HotelTonight negotiates discounted rates at hotels with unfilled rooms or last-minute cancellations — including some very posh places — which means users can score big savings on nicer accommodations than they’re used to if they wait until the last minute. (


The Drizly app lets you order booze online for home delivery. handout

And what about those Red Sox tickets? It’s easier than ever to catch a game on short notice without dealing with partially toothed scalpers or waiting around for Craigslist Charlies. Virtually every ticket resale outlet, including StubHub and Ticketmaster, allows and encourages digital ticket transfers that you can download to your phone. What’s more, StubHub allows users to buy and sell tickets right up until game time for the Red Sox, Celtics, Bruins, and Patriots. (;

Dining out can present problems for the organizationally challenged, especially on a weekend. The widespread adoption of restaurant reservation site OpenTable has been a godsend for the telephone-phobic among us; the problem, of course, is remembering to make a reservation in the first place. Enter Rezhound, which basically hacks the former’s gigantic database. Select your preferred restaurants, time, and party size, and Rezhound will continuously scan OpenTable in real time and text or e-mail you if a table opens up. (;

Reserve is another app designed to rescue your stomach from poor planning. Scroll through its impressive roster of buzz-worthy restaurants and submit a reservation request to a handful of venues. The app’s “concierge” will try to find you a table within your set time range, even at the last minute. Like HotelTonight, Reserve knows about no-shows and can squeeze you in when there’s a cancellation. The elegant and useful interface includes the ability to pay and split the bill within the app itself. (


Still can’t get a table? While nobody likes a line, there’s something to be said for places that don’t take reservations. They are uniquely egalitarian: Get in line, and you’ll get your turn. Giacomo’s Ristorante in the North End has held that neighborhood’s top spot on Yelp for as long as I can remember, and they still don’t accept reservations. The line can grow to absurd lengths, but it moves, and it puts last-second scatterbrains like myself on equal footing with discerning diners who have plotted their night out for weeks. The wait at nearby Neptune Oyster is typically even longer. But they’ll take your phone number and call you when your table’s ready, so you can walk around the neighborhood and work up an appetite (or spoil it with gelato) in the meantime. (Giacomo’s Ristorante, 355 Hanover Street, Boston; Neptune Oyster, 63 Salem Street, Boston)

Other top restaurants that don’t bother with dinner reservations include Toro in the South End, Highland Kitchen in Somerville, and State Park in Cambridge, says Eater Boston’s Rachel Blumenthal. Row 34 in Fort Point holds one-third of its dining area for walk-ins, while Sarma in Winter Hill saves 20 walk-in seats at its bar, plus 16 high-top seats on most nights, where diners can order off the full menu and where, Blumenthal says, “the current cocktail list is spectacular.” (Toro, 1704 Washington Street, Boston; Highland Kitchen, 150 Highland Avenue, Somerville; State Park, 1 Kendall Square, Cambridge; Row 34, 383 Congress Street, Boston; Sarma, 249 Pearl Street, Somerville)


Finally, there is that other great equalizer: the weather. Many Boston hot spots, from Myers + Chang in the South End to Oleana in Cambridge, save their patio tables for walk-in diners, given the unpredictable nature of New England skies. (Myers + Chang, 1145 Washington Street, Boston; Oleana, 134 Hampshire Street, Cambridge)

While you’re on patio patrol, activate your good old Foursquare city-guide app, which can follow your freewheelin’ footsteps around town and, using its proprietary Pilgrim technology, ping you with dining or entertainment tips at just the right place and time. That means it can often tell you the crowd favorite on the menu when you walk into an unfamiliar cafe or alert you to a newly opened bar around the corner that you might like based on your past penchant for craft beer and fish tacos. (

If your plans fell through and you’re looking for a last-minute night in, you’re in luck: In much of Greater Boston, you don’t have to leave the house for anything anymore — especially not food. With the swipe of your smartphone screen, cuisine of any type from some of the city’s finest restaurants arrives at your doorstep in under an hour. “Honey, get the door. It’s the boeuf bourguignon guy.”

Whether it was our appetites, laziness, or outright disdain for human interaction, Boston helped spawn Foodler, which ranks as one of the most established restaurant delivery services in the country along with GrubHub. Both allow users to browse full menus and order meals online from hundreds of area restaurants, from greasy spoons to foodie havens, at normal prices — though fees can be a touch higher at venues that don’t ordinarily deliver. DoorDash can likewise bring you a variety of takeout options — or even make a Dunkin’ Donuts run on your behalf — for a $5.99 delivery fee. (;;


An Instacart shift captain shops for a customer in the South End Whole Foods Market.lane turner/globe staff/file

I like to cook at home instead of relying on takeout, but that entails having groceries on hand — which became a real challenge during the sleepless aftermath of our daughter’s birth a few years back. That’s when we started using Peapod to get our groceries delivered. I was skeptical but desperate, and I’ll admit it was a lifesaver — we probably wouldn’t have eaten otherwise. And despite the delivery fees, we actually saved money; shopping online meant I wasn’t tempted by impulse buys at every endcap. While Peapod offers next-day delivery through Stop & Shop, Instacart allows users to choose from several stores — including Whole Foods, Costco, Market Basket, CVS, Petco, Total Wine, and others — and delivers groceries and a host of other items in as little as one hour. Except, not to me in Quincy. Instacart’s growing local reach does include more than 30 Boston neighborhoods and nearby towns, though. One tough-to-resist bonus for walk-up dwellers: Both services will carry your groceries — even that 30-pound bag of dog food — right up those four flights of stairs to your kitchen if you want, making the delivery fee more than worth it. (;

Amazon’s Prime Now service, which delivers food, groceries, and other goods in one or two hours, has yet to launch in Boston — but could be in the works. In the meantime, Amazon offers its Prime members — who already receive free two-day shipping and streaming video in exchange for their $99 yearly dues — free same-day delivery on thousands of products in much of Greater Boston (including conspicuously omitted Roxbury after public outcry). So if you need some Optimum Nutrition protein powder ASAP — that’s apparently a popular same-day purchase, according to an Amazon spokeswoman, along with Fitbits and Fire TV Sticks — just order by noon and you’ll get your smiling cardboard box by 9 p.m., even on Sunday. (

And if you can’t find it on Amazon, there’s always Postmates, an app that sends your neighbors scrambling around town to do your bidding. Maybe you’ve got a hankering for Anna’s Taqueria, and you’re all out of trash bags, and you need a new iPhone charger, too. Real Bostonians will take to their bikes or cars and fetch these items for you within an hour, as though you are the overlord of some ancient fiefdom — assuming the overlord had to wrangle with a somewhat complicated fee structure that includes a delivery charge ($6 and up) and a 9 percent service charge, plus the option to tip within the app. For $9.99 a month, users can dodge delivery and service fees on every order over $30. Postmates currently serves Boston, Brookline, Cambridge, and Somerville. One thing it can’t bring to your Massachusetts address, though, is alcohol. (

Postmates employee Margaret Purdy of Somerville prepares to make a delivery.Harrison Hill/file

For urgent relaxation (or a more romantic last-minute gift if your partner wasn’t wowed by last year’s printed-out e-receipt), you can book a massage therapist to arrive at your home, hotel, or office in as little as an hour. I’m very ticklish and somewhat introverted, so the idea of someone showing up at my house to massage me is, frankly, my personal nightmare. But if that sounds relaxing to you, two of the biggest on-demand massage apps — Soothe and Zeel — operate in the Boston area and allow you to book a house call from a certified massage therapist. Rates start at $99 for a one-hour massage and, as with most apps, the awkward tipping process is taken care of automatically. (;

I prefer to unwind the old-fashioned way: ordering beer online. We were expecting guests on a recent Friday night, and some thirsty writer type had polished off all the beer in the house. Between work and kid duties, I knew I wouldn’t have time to make a beer run before everyone arrived, so I placed an order on Boston-founded booze-delivery app Drizly. About an hour later, a friendly guy from my local liquor store showed up on my porch with two cold 12-packs. This wasn’t just convenient; the sight of him made me grin from ear to ear. You have to remember that until about 12 years ago, we couldn’t even buy beer on Sundays in Massachusetts! And this little miracle works for gift deliveries, too, as long as the recipient is over 21. So if you forgot a birthday or big anniversary, you can send the deserving celebrant a bottle of wine or bubbly right away, as if you’d planned the thoughtful gift for weeks. (

It seems the world has never been a more forgiving place for us last-minute people. In fact, I may never have to sleep in a car again. But even if I do, at least I’ll be able to get some beer delivered to the back seat.

Jon Gorey is a frequent contributor to the Globe Magazine. Send comments to