AFTER Judith Himber’s husband died in 2010, she didn’t know what to do with herself. “It was a stunning loss,” said Ms. Himber, 73, who works full time as a clinical psychologist in Cambridge, Mass.

She was not sure if she would ever want another relationship; her marriage had been long and happy. But after two years alone she realized that she did want a partner. One problem: She hadn’t been on a date in 33 years.

“I felt old, unattractive and the idea seemed ludicrous,” she said. Still, she joined Match.com, JDate and eHarmony, online dating sites. She found it “excruciating.”

“Signing on each morning and seeing that over 100 guys had looked at my profile and none had contacted me was dreadful,” she said.

She also called Peggy Wolman, a matchmaker and dating coach, paying $2,500 for her services, Ms. Wolman’s starting rate. Together, they explored what Ms. Himber, a grandmother of four, was looking for in a mate. Ms. Wolman and her husband, Richard, a psychologist, also administered a personality test and “spiritual inventory.”