Matches without the burn

Worcester-born entrepreneur eases singles’ fear of rejection
By Pamela H. Sacks
TELEGRAM & GAZETTE

2002

BOSTON — In an era defined by the speed of the Pentium computer chip, someone was bound to put the dating game on a really, really fast track.

Software and marketing whiz Tom Jaffee figured an encounter of 5 to 10 minutes was plenty of time to size up a member of the opposite sex. So he created 8minuteDating, a surefire way to eliminate excruciating blind dates, or that humiliating business with the telephone. Should I call? Will it ever ring?

“With 8minuteDating, the investment of time is minimal,” Mr. Jaffee said cheerily. “The pain of rejection is dramatically minimized.”

But, of course, quick rejection is not what Mr. Jaffee is selling. Already, he said, his dating service, now 17 months old and spreading rapidly across the country, can boast its first engagement. And during a trip to Italy, at that.

Mr. Jaffee, 39, a native of Worcester, was feeling a bit bored after a highly successful decade riding the high-tech wave. He noticed that the concept of round-robin dating was popping up in Boston and other large cities.

“I was looking for a new challenge and wanted something to wrap my brain around,” he said. “I knew it was a great idea, something whose time had come.”
Mr. Jaffee, whose credentials include a master’s degree in marketing from Columbia University, devised an approach that combined brief, face-to-face encounters with Internet matchmaking. He thought people within a 10-year age range would enjoy each other’s company.
He came up with this scheme:
Singles sign up on the 8minuteDating Web site for an “event,” which is held at a bar or restaurant. At each gathering, there are an equal number of men and women, and everyone reveals only a first name. The cost is $28.88, although it can be somewhat more if there is a wine tasting involved.
The computer creates eight dating combinations for each person, which are listed on a card handed out at the start of the event. Afterward, the participant indicates, via e-mail within 24 hours, who sparked an interest. If the feeling is mutual, the computer acts as go-between, providing full name and contact information.
“It’s a whole algorithm to make sure no one sits with the same person twice and everyone knows where to go,” Mr. Jaffee said.
The algorithm was in full swing the other evening at The Exchange on State Street, where 50 singles between the ages of 35 and 45 gathered for a dating swap. Initially, the men seemed to prefer each other’s company, as did the women. They nibbled hors d’oeuvres and sipped drinks with pop music blaring in the background.
Mr. Jaffee recruits and trains people to organize events, and they share in the night’s take. The organizers, too, use only first names. This was Kelly’s debut, and she exhibited all the style of a Park Avenue hostess while greeting her “guests.”
Perched on a stool, Mr. Jaffee pointed out Francis, a dashing-looking fellow with dark hair and a thick mustache.
“I’ve seen him at half a dozen events,” Mr. Jaffee said.
Francis, who is from Melrose, came over to chat and confirmed that he was not a newcomer to 8minuteDating.
“It’s nice because people here are serious to various degrees,” he said. “You’re pretty confident and hopeful they’re not married.”
As the men and women headed to a function room to get down to business, Mr. Jaffee felt the need to clarify.
“It’s not, `Am I madly in love? Are the bells ringing?’ but, `I enjoyed that conversation. I’d like to meet that person again,’ ” he said. “The goal is to find someone you might want to spend more time with.”
Couples sat at small round tables and banquettes, talking amiably, prompting Mr. Jaffee to remark that the set-up generally attracts conversationalists. Yet, those who find themselves dumbstruck need not panic. 8minuteDating provides a crib sheet with questions: “Where are you from? What kind of work do you do? Do you have any brothers or sisters? What kind of sports do you like?”
“I love to look at body language,” Mr. Jaffee remarked in a stage whisper as he glanced around the room. “Look at him. He’s leaning toward her, and they’re both smiling.”
Mr. Jaffee stressed the software behind his dating system is complex and took 18 months to develop. He came to the task with no shortage of experience, having spent half a dozen years at Microsoft Corp. headquarters in Redmond, Wash., as part of the team that launched Windows 3.0.
When its successor, Windows 95, was about to come on the market, Mr. Jaffee realized the program was difficult to use. He started his own company, WinStruct, and developed training software for Windows 95 and an array of other programs designed for home and business use.
By 1997, Mr. Jaffee, who has a degree in human factors engineering from Tufts University, was wealthy and ready to move back to New England to be near his family. His parents, Stuart and Sylvia Jaffee, live in Worcester, where they raised their four sons.
Taking WinStruct with him, Mr. Jaffee settled in Boston in November 1997. He still runs the company part time.
Within a couple of years, he found he was bored, and the dilemma of dating caught his attention.
“Some people like to build, some like to manage,” he noted. “I felt restless. I wanted something new.”
Back at the lounge, Mr. Jaffee confided that some people are embarrassed to be at a dating event — a feeling he said mystifies him — and might not want to talk with a reporter.
As it turned out, Catharine from Boston immediately approached during the intermission, eager to share her thoughts. Tall, blond and tanned, she looked as if she would have no trouble on the dating circuit.
“I’m in venture capital, and I work all the time,” she explained. “I work and work out.”
She added that she came with no expectations and was pleasantly surprised. She met one man she’d like to see again. She has single friends and all have trouble meeting men, so she agreed to try 8minuteDating and report back.
“I’m kind of like the canary in the coal mine,” Catharine said, breaking into gales of laughter.
Debby, a single mother from Newton, stood to one side, appearing a bit shell shocked, though she, too, had met one person with possibilities. This was the fourth event she had signed up for. The others were overbooked with women, so she had to wait her turn.
At 44, Debby said, she would have preferred to meet people a bit older. She tried putting her name on a list for 45- to 55-year-olds, but no men expressed an interest.
“I think it’s the whole dating thing, with the fear of rejection,” she mused.
As Debby moved on, Adam approached. Lanky and laconic, Adam indicated he was willing to converse, if briefly.
Q: Have you been to one of these events before?
A: I’ve been to two or three.
Q: What happened?
A: I got some dates.
Q: What about tonight, any prospects?
A: I liked one of four.
Q: What did you like about her?
A: Sharp mind.
Mr. Jaffee checked his watch as the men and women settled in for the second session. He said he was expected at an event across the city, this one for singles between ages 25 and 35.
One last question: Does Mr. Jaffee have a girlfriend? He smiled and said “yes.”
But he met her the old-fashioned way — at a party.