May 21, 2019

Matchmaking as an entrepreneurial labor of love

Talia Goldstein, founder of Three Day Rule. Photo from

Many women are adopting the same outlook in forging their careers as they are in finding their bashert: Never settle. Los Angeles resident Talia Goldstein is one of them, as that mindset led her to both her husband and her entrepreneurial path as founder of the dating company Three Day Rule (TDR).

Armed with a degree from Tulane University, Goldstein landed coveted associate and segment producer positions at VH1 and E! Entertainment. However, her observations about singles and desire to be of service to others paved the way to TDR in 2010.

In the beginning, her company focused on producing singles events. She got the inspiration for the name from the ’90s movie “Swingers” and its characters’ discussion of the “Three Day Rule.” “Guys thought you had to wait three days after getting a girl’s number before you called her. We definitely don’t believe in that rule anymore, but we still love the name,” Goldstein said.

In 2013, she reinvented TDR as a full-service dating company ( which covers nine U.S. cities. TDR now has 39 employees, including 32 matchmakers nationwide, to help “hundreds of clients” a year, Goldstein said. Currently, 70,000 people are in TDR’s database.  

Goldstein’s parents’ happy 40-year marriage influenced her business model. Her American-born father was doing his medical residency in Israel when he met her mother, who is a social worker. “They instilled in me the understanding that being judgmental may prevent one person from making a meaningful connection with another,” said Goldstein, who is 37 and grew up in Orange County.

Anybody can enroll in Three Day Rule’s database free of charge. In 2017, TDR expanded to include yearlong VIP nationwide matchmaking packages with two hands-on matchmakers and personalized concierge services ($35,000) in addition to its basic packages, starting at $4,000 for three months of matching in one’s city of residence.   

TDR was one of just a few dating companies to secure “Series A” funding in 2016, bringing in $1.2 million when venture capital investment for dating companies fell overall. To get there, however, Goldstein faced judgmental thinking from investors.

“I was pregnant both times I set out to raise capital,” she said. “The first time, I hid my pregnancy under trench coats and ponchos. Business advisers warned me that (financiers) saw pregnancy as a red flag. Later, I decided not to hide my second pregnancy, as I felt my company had such excellent metrics and traction that it would not make a difference.”

But it did. Male investors told her that they preferred to wait to commit until she had her second baby. Days after leaving the hospital, she finally closed the deal with nine investors.

“I hope this mentality will change, as women should not have to decide between starting a family and becoming an entrepreneur,” she stated.

TDR matchmakers develop a customized plan for clients who have been dating for years, had bad experiences with dating sites, or are newly divorced or widowed. While she believes online dating can be effective, she found daters spend an average of 13 hours a week online.

“If you have a full-time job and a full life, finding the time to do it effectively is hard,” she conceded. “When you factor in that other people are busy, it makes sense that one may not get the replies online he or she may be hoping for. This can make the process demoralizing.”

Phil Wallace, 35, of West Los Angeles, a longtime online site user, said he was pleased that TDR communicated with women on his behalf. He said his dating life has blossomed since his enrollment, with four excellent prospects.

“I didn’t have to worry about them not looking like their pictures. [Goldstein] had met with all of them in advance. Deal-breakers were addressed ahead of time, so there were no sudden, shocking revelations that made me question my date’s character,” he said.

Adelle Gomelsky Kelleher, 37, who was matched with now-husband David Kelleher, felt relief that “someone who had more networking and resources than I did was out there looking.” She used a popular Jewish dating site, but was frustrated with constantly seeing the same men whom she had met at Jewish singles events. At the same time, she found her perceptions of what made a man an ideal candidate shifted.

Gomelsky Kelleher said the process enabled her to relax and enjoy her dates more while also getting her to look beyond first impressions of a possible match to “how I treated all people overall.”

Goldstein pointed out the “mental checklist of wants” is a common mistake among daters: “She may indicate she wants a man with dark hair who is 6 feet tall. But by putting up these filters, she may miss out on somebody who happens to be 5-10 and blond, who could have been her soul mate.”

Goldstein’s business model contrasts with others that match only paid members. People with limited budgets still have a shot at being paired with a paying member if common interests, values and preferences line up.

The old adage goes that you can’t win if you don’t play. Even rookies may get lucky during their first times at bat. Allie Jablon, 41, who avoided online dating because of its “impersonal” nature, was introduced to her husband within a week of signing with TDR.

“Having [a matchmaker] who gets to know you before you are introduced to men is much more productive and fulfilling in my opinion,” said the Hollywood resident. “Where online dating can feel like a job to some, dating should be a joy, not a job.”

‘The Great Jewish Love Debate’

“The women are on this side, and the men are on that side. No exceptions.” 

With those words, Brian Howie, author of “How to Find Love in 60 Seconds,” kicked off The Great Jewish Love Debate at Sinai Temple in Westwood on Oct. 27.

Howie, who is not Jewish, founded The Great Love Debate earlier this year after his book came out. It was a means of answering the question, “Why are we all single?” The first event took place in Santa Barbara, and the tour has been extended through 2015, covering more than 150 cities worldwide. 

“I’ve always liked the town hall-style discussion and debate,” Howie told the Journal.

Attendees were asked to dress to impress, or more specifically, to dress like they would on a first date. Women with blow-dried tresses wore stilettos and short skirts; men sported slicked-back hair, patent leather shoes and striped dress shirts.

“This is the 57th Great Love Debate, but this is the first Jewish one!” Howie announced to the audience, which responded with hoots and applause.

It was also the first Great Love Debate in which Howie didn’t participate in the onstage panel. 

 “It’s because I didn’t think I was Jewish enough,” said Howie, whose paternal grandmother was Jewish. When the debate, co-sponsored by Sinai’s young professionals group ATID, officially started, Howie slipped away and didn’t reappear until the after-party.

Lori Gottlieb, a relationship therapist and best-selling New York Times author of “Marry Him: The Case for Settling for Mr. Good Enough,” served as event moderator. Nine years ago, as a single woman, she chose to become pregnant and now is the proud parent of an 8-year-old son. Gottlieb said her mom immediately asked if the donor for her insemination was Jewish. 

“She’s a typical Jewish mother,” Gottlieb said, laughing.

The panelists included Talia Goldstein, co-founder of the matchmaking website Three Day Rule; author Adam Gilad; Lisa Darsonval, founder of Santa Barbara Matchmaking; makeover expert Kimberly Seltzer; and dating coach David Wygant. 

The debate kicked off with a sharing session of horrifying dating moments contributed by the audience. “Let’s get to know you guys,” Gottlieb said. 

“I realized my fly was down,” confessed one guy. 

 “I got thrown up on,” a woman said. 

“Halfway through the date,” another woman chimed in, “he told me Jesus was the savior.” 

During the debate, Gottlieb called up volunteers to act out typical pickup scenarios. Before each scene, a guy was selected and told to choose the most attractive girl in the audience to join him. 

“Imagine you’re at Starbucks,” Gottlieb told one set of volunteers. 

The girl pretended to be on her phone, drinking a coffee, as the guy circled her, unsure of how to approach her — until he finally piped up and said the situation was too awkward. The audience gave input, and finally one of the audience’s older members stood up and broke it down for the young volunteers. 

“If you want to meet a girl, you offer her to buy a cup of coffee,” the woman said. “Say that you noticed she finished her drink and ask if she’d like another one.” 

A 20-something seated nearby whispered to her friend, “Now that’s classy!”

Another scene played out was grocery shopping at the market. Panelist Gilad gave some pointers to the men: “When I’m at a supermarket and I see an attractive woman, I take her shopping cart.” 

Of course, there’s more to his tactic. The woman usually says something like, “Hey, that’s my cart,” to which he responds: “Hmm, but I like yours better.” If all goes well, she laughs and he scores a date.

About an hour after the debate began, the event concluded with closing statements from the panelists and the men (the women were never asked for one). Then the shmoozing began. Singles lined up to ask the panelists personal questions, wine was poured, and phone numbers were exchanged. 

All in all, one more notch in Brian Howie’s belt.