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n February 2009, the Globe Magazine debuted Dinner with Cupid, a column that aims to match up Boston’s singles, send them out on blind dates at local eateries, and have them report back about what happened.It was one part social experiment, one part schadenfreude for the smug married crowd, and one part journalistic attempt to document that fundamental aspect of the human condition — the quest for love — often left unexamined in the news section.Center, from left: Emily Kanzer, Kathryn Peneyra, and Lydia Zepeda. At the anniversary event, he tried to give the other singles matchmaking guidance, suggesting some offline venues — the gym, Meetup groups, the bar scene. “It’s an excuse to see each other, but also if we happen to fall in love, yay!” Those looking for love need to try harder, Tucker says.

(At least, we’re still waiting for that wedding invitation.) Like our singles, Cupid has suffered through the indignities of the dating life.To fete the column’s anniversary, we assembled some of our liveliest former daters on a frigid winter’s night at Assaggio restaurant in the North End for some behind-the-scenes dishing.We asked them to fess up about what really happened during and after their date, how they feel about the Cupid experience, and their ongoing search for modern love.The risk is real: Women and men they know have had their drinks spiked with roofies.For Emily, the age-old debate of who pays on a first date is filtered through this prism. ”For all of the drama, these daters have faith that the apps’ algorithms will ultimately pay off.

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