It was wedding season, summer 2005. In addition to planning his own upcoming nuptials, nearly every weekend entrepreneur Timothy Chi traveled to the ceremony of a close friend or family member. Though the celebrations were joyful, organizing them was not.

“I attended so many weddings, and I heard the pain so many times of brides complaining of x, y and z,” says Chi, cofounder of the new startup Web site WeddingWire. “I was feeling the pain myself going through it, and it all bubbled up into that ‘A ha!’ moment of there must be something I can do.”

What Chi and his colleagues did was develop WeddingWire (www.weddingwire.com). The site, which officially launched in May, is designed to take the pain out of planning a wedding by connecting engaged couples free of charge to nationwide vendors – the photographers, caterers, musicians and wedding planners who help a bride and groom’s special day go off without a hitch.

“The trend is everyone is starting to plan weddings online,” says Chi. “Then you have this highly fragmented group of wedding vendors who haven’t necessarily moved online and who aren’t being found. We built a tech platform…to create a more efficient marketplace for them to find each other.”

Chi’s prior experience with joining disparate groups of Internet users helped him see just how WeddingWire could fill a need in the $50 billion wedding industry. Chi honed his skills as one of the cofounders of Blackboard, an Internet education software startup headquartered in DC. Blackboard connects students and faculty in an online environment, and the publicly held company just reported $55.3 million in first quarter 2007 revenue.

Chi’s success in the DC area encouraged him to launch WeddingWire just outside the city in Chevy Chase, Md.

“The DC community has a great network of entrepreneurs in technology and venture capital support for growing businesses,” he says. “Fostering a technology company in DC, you aren’t necessarily one of a trillion like you might be in Silicon Valley.”

Most wedding Web sites, such as The Knot, are information-oriented and designed to educate the bride about the wedding-planning process, says Chi. WeddingWire, however, is unique in that it gives brides the tools to actually execute their weddings.

Such tools include a map-based vendor catalog that’s searchable by category, price and location; SmartMatch, a comparison technology that allows couples to receive estimates from vendors; and vendor reviews by real-life couples. WeddingWire also uses some of the most popular Internet trends, such as user-generated content and social networking, to its advantage.

“We are not the authority on why lime green dresses are in this fall,” says Chi. “The user base decides what’s good and what’s not, and people can post their own discussions and talk about it.”

Other highlights include a community of vendors available to discuss wedding-related questions, such as how much to tip the band. Brides can also organize their wedding plans into online “binders” and can even share access with their wedding planners or others.

Although WeddingWire is packed with functionality for brides and grooms, the company is equally interested in serving their vendors. Thus, it’s free for vendors to post their profiles on the site, and they’re charged only when they book clients through SmartMatch. This risk-free advertising hooked Amy and Srinu Regeti, owners of Regeti’s Photography (www.regetis.com). In fact, they dropped their prints magazine ads in favor of advertising through WeddingWire, which Amy estimates saves them thousands of dollars while providing them with a better return on their advertising investment. The couple, who are booked to shoot 36 DC-area weddings this year, receives 80 percent of their business through their Web site. Much of that is from personal referrals, says Amy.

“WeddingWire is the perfect medium because they have vendor reviews,” she adds. “Girls get on there and write their power blurb. It’s stronger when the bride writes what was so great about our services.”

WeddingWire provides a built-in community not only for brides but also for vendors, adds local wedding planner Michele Hodges, of Michele Hodges Events (www.michelehodgesevents.com). She posted her profile on the site after hearing about it from wedding photographer Steve Canning (www.stevecanningphotography.com).

“The Knot is getting a lot less personal because it’s so huge, and vendors don’t recommend other vendors on that site,” she says. “It’s more personal the way that WeddingWire does it.”

Canning is also pleased with the site.

“It’s fairly early in the process, but it’s been a great tool for me already,” he says. “It seems like they are really forward-thinking people [at WeddingWire], and they are going to be on top of the next new thing.”