Anne & Michael in Chicago, IL

Anne's first Match.com date was also her last. Both Anne and Michael joined the site only two weeks before they met at a Manhattan wine bar, where they talked until the place closed. Almost a year-and-a-half later, Michael surprised Anne with a proposal. The Bride Anne Kennedy, 28, attorney The Groom Michael McGuire, 28, financial services manager The Date April 18 The couple lived in New York City, so they hired a consultant to help plan their wedding in Anne’s hometown of Chicago. Anne, a University of Michigan graduate, also wanted to avoid having the wedding during football season -- when guests would be looking for a TV -- so they picked April, which was 18 months away. For an elegant vibe with a splash of color, they went with a black-and-hot-pink palette and let their library venue set a book theme.