It started with a seductive e-mail subject line: “Want a free trip to Chicago?”

Why, yes. Yes, I would like a free trip to Chicago. 

An opt-in box checked “yes” many months ago ensures I get periodic special offers from Luxury Link and its partners. In order to enter to win this “ultimate gourmet Chicago weekend, curated by celeb chef Rick Bayless,” I first had to enroll in OpenSky, Luxury Link’s partner.

And what an eye-opener that was.

Ah, OpenSky, where have you been all my shopping life?

For the uninitiated, OpenSky marries the serendipity of in-person shopping — in a global mall, marketplace, boutique, or high-end shop — with you-you-you and your wants, plus your computer or mobile device.

Here’s how it works: Sign onto opensky.com and click through a visually appealing, multiple-choice “taste” survey of eight categories. We’re talking beauty, apparel, and accessories. We’re talking electronics, kids’ stuff, and food. We’re talking home items and healthy living.

Clever devil is OpenSky, displaying tantalising meals, plated up and pretty, for your perusal. Are you a down-home cookin’ girl, a continental sophisticate, a “just deliver it to my walk-up right now” person? You’re all three? No problem. OpenSky is learning about your taste with each keystroke, making little algorithmic notes along the way. How about clothes: Are you into college-logo-themed Snugglies? Prepster garb? Yoga togs? Euro chic? Click, click, click. OpenSky is creating an uber-personal cyber shop, just for you.

Fickle, like me? No worries. You can change your preferences any time, and you can also change your selection of “curators” — celebrity shoppers who suggest amazing finds 24/7, based on your profile. (You can also pick additional curators outside of what the site picks for you. You KNOW I’m auto-following Guy Fieri!)

My profile tastes resulted in an array of products ranging from a darling Amy Matto beach dress recommended by Kelly Rutherford, to a pair of hot Habitual Milton trouser Jeans curated by Molly Sims, to a nifty little Purse Protector bag organiser spotted and shared by Julie Morgenstern. Average Joes (and Josettes, as in my case) can also recommend, share, and “heart” (love) items on this brilliant e-commerce site.

It even offers the retail-therapy-starved an opportunity for altruism during initial sign-up (“Here’s $90 to give to three of your favorite people when they join OpenSky!”), but the greedy and impatient can bypass this completely (side note: Sorry, Misha, Ross, and Paulo!) and get shopping!

The market apparently loves the impatient shopper and this fetching, Pinterest-esque site: According to an article by Peter Kafka on allthingsd.com, OpenSky has raised US$49 million in financing, with more than 600,000 members signed up and spending about US$50 per shopping “trip” — more than double Amazon’s average order of US$22, Kafka writes.

So where and how can newsmedia companies capitalise on this “push product” versus search-for-it mentality? Well, rich-media digital ads that let customers customise the ad content they’re seeing is one way.

Example: The agencies responsible for the Seattle Convention and Visitors Bureau (Lion New Media and Copacino + Fujikado) crafted a super-fun user experience for placement on spokesman.com. Working with our Senior Digital Media Sales Executive Arin Martinez, SCVB wanted our Web and mobile users to plan “two days in Seattle.” The campaign lets you play around with what you want to do, and get advice from “curators” (there’s that word again) who know the city well. From Elysian Brewing Company and Fran’s Chocolates to the Space Needle and Ray’s Boathouse, your “viewing an ad” experience just become actual useful, fun, interactive content. 

Another way that newsmedia companies can learn from this push approach is through contextualised advertising in customised e-newsletters. Just this month, for example, Ryan Pitts, our senior editor for digital media, introduced highly customisable newsletters that Web and mobile users can craft based on frequency, topics, key words, specific reporters, etc.

Our task on the marketing side is to pitch and sell content-like ads that match a user’s specified e-newsletter topics. For example, my e-newsletter would include ads for pet-related businesses, restaurants, massage therapists, and bookstores. My counterpart in the marketing division might see ads from vintage record stores, theater and symphony concert halls, and children’s clothing boutiques.

The point is, consumers have become selective, savvy, and time-starved. But they are still willing to spend time with ad content that speaks to them, or with ad content that their friends (or the friends they wish they had — hello, Guy!) recommend to them. In the meantime, I just got a notification from my pals Liz Lange and Jane Wagman: “The clean, simple design of this cuff means it will go with EVERYTHING.”

I agree. Click.

Adia Kibur Geometric Gold Cuff, coming to a mailbox near you!