A Little Chutzpah Goes a Long Way

Emily Abigail Waife summoned up a bit of chutzpah in 2013, after talking it over with friends. She wanted to tell Eli Michael Kaufman she had feelings for him.

“I always thought he was funny and I loved his passion for Judaism,” said Ms. Waife, a paternal great-great granddaughter of Sholem Aleichem, the Yiddish author and playwright best known for his stories of “Tevye the Dairyman,” the inspiration for the Broadway musical “Fiddler on the Roof.’’

She had joined the on-campus Jewish organization Hillel, of which Mr. Kaufman was president, after she first got to Goucher College, from which they each graduated, she cum laude. “He was that guy everyone knew on campus.”

He was clueless as her feelings for him grew during spring semester of freshman year after she joined the Hillel board and regularly teamed up with him after Shabbat dinners to play the board game Settlers of Catan. (They were also in the same Judaic studies class and sometimes studied together in the library).

Her bold move blindsided him after spring break. After giving him the cold shoulder for days, she sent him a text saying she needed to speak to him, and then hurried over to his library study room to profess her feelings.

“I never thought of Emily in that way,” he said. “ She told me she likes me,’’ and then he recalled telling her, “‘Oh, OK. I have to think about it for a second.”

She described it as “a stressful, very long week.”

He avoided her on campus, and did not have an answer when she inquired after their next game of Settlers the following Friday, but 24 hours later, after another game, as they walked back to their dorms he answered her with a kiss.

Two weeks later, he took her on a mystery date off-campus — a picnic on Federal Hill in Baltimore — and they made their dating official that evening by telling their parents.

The couple, both 27, now live in Chicago where Mr. Kaufman is a sales manager at Packback, an education technology start-up company that promotes student engagement and critical thinking. Ms. Waife, who will be taking the groom’s name, is the administrative assistant at Chicago Sinai Congregation.

In March 2019, Mr. Kaufman proposed while Ms. Waife was visiting a friend in Charlotte, N.C. She thought he was still in Chicago working on a presentation in a coffee shop near their apartment. Just after she took a photograph of her friend and her friend’s fiancé at a fountain in Freedom Park, Ms. Waife turned around and saw Mr. Kaufman standing there.

“Is this real, are you here,’’ said Ms. Waife, and after he said a few words, he got down on one knee. He further surprised her by inviting their parents — his from Toledo, Ohio, and hers from Needham, Mass. — as well as her sister in Chapel Hill and her boyfriend, and his brother from Chicago to celebrate at an Italian restaurant.

The couple planned to get married May 24 at Hotel Allegro in Chicago, expecting 200 guests, before the coronavirus outbreak. Instead, Cantor Jamie Gloth, remotely, and Rabbi David M. Russo, in-person, conducted a religious ceremony outside Anshe Emet synagogue on that date with 177 screens, probably about 350 guests, tuning in via Zoom. Attending the actual ceremony were Mr. Kaufman’s brother and his girlfriend, and two of Ms. Waife’s bridesmaids, who signed their ketubah.

“I did feel energy from the people watching,” she said. “We were just so happy.”

On June 25 — the first date they could get a marriage certificate from Cook County in Illinois — they were legally married at their apartment. Cantor Gloth officiated, again remotely.