• by David Berkowitz , February 6, 2007

Though I spend my day working on client proposals, at night, during the past couple of months, I was working on one proposal that mattered more than all the others combined. More often than not, it led me to the shortcomings of search engines. Here's where search worked, and where it could use some work, in the context of planning a major life event.

Surfing the 4 Cs: While the timing of the proposal was a surprise, Cara and I started seriously thinking about our engagement several months ago. Before Thanksgiving, we started shopping for rings both in stores and also online.

I understand consumers have come to embrace online shopping for high-ticket items like jewelry; comScore reported that the online retail sales for the jewelry & watches category were up 67% in the 2006 holiday season over the previous year -- the biggest jump of any category. Some aspects of buying diamond jewelry translate well to online shopping, namely when comparing technical specifications like the 4 Cs - cut, clarity, color, and carat. Yet when buying an engagement ring, there's one F that can be the biggest differentiator: fire -- how well diamonds reflect light and sparkle. That proved to be the biggest differentiator among the various stones I saw, and the way to best gauge it is to see it in person.

Have ring, will travel. I decided to propose to Cara on a vacation we planned in Mexico's Mayan Riviera, in the Yucatán along the Caribbean. Searching for flights was the easiest part of the process, with Kayak and Sidestep proving especially helpful. Flights are, ultimately, a commodity, and the best travel search engines make comparing commodities on price and convenience an easy, even enjoyable process.

Hotels, however, are not a commodity. Along with cost and convenience, there's service, views from the room, the quality of the food, how crowded it is, how close it is to the beach, if there's in-room Internet access, and all those small touches that add up to the experience. No single site covered all bases, though some like Hotels.com were more useful for hotel descriptions and others like TripAdvisor were better for reviews.

I knew we'd want to make a lot of phone calls after the proposal, so I set up a Skype account with ample credits for calling out and a Skype-In phone number where others could reach us through a New York City area code. I also bought an Ipevo Free-1 phone handset through Amazon, which plugs into a USB port for easy calling (at $30, it's a steal, and the quality's exceptional). The one catch for making that work: I needed a hotel with in-room broadband Internet access. That was almost harder than finding the right ring.

Hotels.com said just about every half-decent hotel and resort in the Mayan Riviera had some sort of Internet access, but it was impossible to determine whether that meant in the room or a business center, and whether it was dial-up or broadband. The Web sites of the hotels themselves were generally more honest, though sometimes vague. I even Googled phrases like "hotels internet access mayan riviera," and no form of drilling down helped. Ultimately, after booking one hotel that seemed like a fit, I called Hotels.com and they told me the property only had Internet access in the business center. Before booking another hotel, I called its front desk and found someone whose English was just barely good enough to reassure me I could get online there. Ultimately, the hotel, the Ceiba del Mar in the sleepy fishing village of Puerto Morelos, proved to be the most wonderful place Cara and I had ever stayed. (Cara didn't know we were staying there until we got there; she thought we were staying at a hotel in Playa del Carmen aptly named The Illusion).

Arriving in style. As another surprise treat for Cara for when we landed at the Cancun airport, I arranged for a car to pick us up. I went with a business atop the natural search rankings, CancunLimo.com. I glanced at the ads, but they were a mixed bag, with many targeted to my home locale, even though I was explicitly searching for a ride in Cancun.

Ice, ice baby. When buying the ring, I found a retailer through a free-standing insert in Cara's subscription to The New York Times. I just used Google to help find the nearest location. A sales associate at the jeweler helped me find the right band and then the right stone to go with it. I was set.

I proposed the first night of our trip, down on one knee on a starlit, secluded beach right on the sea's edge, with the cool, silky, white sand beneath us and a breeze ushering in the excitement of the evening. It was so dark that she said "yes" well before she could see the ring.

One other surprise was still ahead: instead of returning to New York that Friday, we'd be spending the weekend in Dallas with her parents, whom she hadn't expected to see for at least a couple months more.

In the meantime, during our stay on the beach, Cara was really  protective of her new ring. She didn't want it ruined by sand, sea, or suntan lotion, so I suggested that she search online for tips on ring care. She had no interest. She was going to see her parents soon, and learning how to care for an engagement ring was an occasion for a daughter to learn from her mother. Even when a search engine can provide the answers, the truly most relevant answers are the ones that come from Mom.