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After losing her husband, George—her one and only since high school prom—to cancer, fifty-year-old Debbie Weiss found herself opening a new chapter of life that she didn’t know how to start.

Initially, she binge-watched Netflix and drank Manhattans. Then she became a dating monster—starting with J-Date and then moving on to multiple other sites. Soon, Debbie was averaging two dates a day; in the bl...