CBS News: First-ever YentaCon held in Philadelphia for Jewish singles and matchmakers

PHILADELPHIA (CBS) -- More than 50 women and men from around the world gathered at the Weitzman National Museum of American Jewish History on Thursday for the first-ever "YentaCon," a conference for matchmakers who cater to Jewish singles.

Matchmakers came to Philadelphia from as far away as Canada and Israel.

"My first match, I was 16 years old," Bonnie Winston, who's from New York, said. "It was a calling, and I think that the matchmakers that are here, are here because it's a calling."

One of the goals for matchmakers at the conference is to take back the Yiddish word, yenta, which means a gossip or a busybody.

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The New York Post: Inaugural YentaCon, the 'First Jewish Matchmaking Conference'

“It’s the year of the yenta,” declared NYC yenta Bonnie Winston, who said that matchmakers are working overtime trying to pair up singles “looking for a Jewish connection” in the wake of the Oct. 7 Hamas attacks and amid a surge in antisemitism.

“We are all in one room to support one another, despite our differences, to help our Jewish clients find love,” she said to a sea of emphatic nods.

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The Harvard Crimson: The Matchmakers of Harvard Magazine

“I like the idea of personal ads, because that is exactly what they are — they’re personal,” says celebrity matchmaker Bonnie Winston, who has placed ads in Harvard Magazine since the late 2000s. “It’s a very good way for me to find quality bachelors and bachelorettes to match my clients up with."

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Best Life: The 25 Worst First Date Questions

5 | How much did that cost?

Nope nope nope. Whether it's their apartment, watch, or a clearly luxe handbag—it's none of your business. "It's just plain tacky, and also will make you appear shallow and only concerned with money," says Bonnie Winston, celebrity matchmaker and relationship expert. "You can compliment something without wanting to qualify it with a price."

Well + Good: How Beige Flags in a Relationship Differ From Red and Green Flags—And What To Do About Them

What to do if you notice beige flags in your relationship

Identifying the beige flags is the first step in knowing how to handle them. But what happens when you can’t tell what color the flag is to begin with? Some people may read red as beige and green as red, depending on how they show up to and interpret their own interpersonal relationships.

“One of the most common issues my clients have is confusing what is a red flag versus a beige flag versus a green flag," says Bonnie Winston, matchmaker and relationship expert. "So, as a result, they want to break up too soon with a good partner, or they stay too long with the wrong partner."

Insider Magazine: 20 Fun First Date Ideas That'll Keep You Engaged and Entertained, According to Dating Coaches

17. Try a food truck

Forgo the stuffy restaurant for some casual eats from a local food truck on your next first date, says Bonnie Winston, celebrity matchmaker and relationship expert. 

Not only is this typically more affordable than a fancy restaurant, but the laid-back environment might help you feel more at ease. Best of all, you won't have to deal with waving down your server or waiting for the check, which means you can fully focus on getting to know each other better.

Success Magazine: Matchmaker Consultant for ‘The Marvelous Mrs. Maisel’ Shares Top Relationship Red Flags

Bonnie Winston began her career as a matchmaker at the age of 16. While dancing with her friends at a New York City club in 1979, she set up one of her friends with a guy Winston had met. Six years later, the matched couple got married. Winston unofficially continued the practice for the next 30 years—successfully matching hundreds of couples. In 2013, she made it official by creating a business, aptly named Bonnie Winston Matchmaker.

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Dating News Magazine: Matchmaker Bonnie Winston Builds Long-Lasting Connections in the Dating Scene

Many singles searching for love turn to online dating, thinking it’s their best, or even only, chance to meet compatible partners. That’s because the number of online daters grows each year.

In 2017, some 28.9 million users in the US turned to virtual platforms to meet potential partners, and that number increased to 44.2 million in 2020. Estimates for 2025 suggest that 53.3 million singles will be using online dating platforms.

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Authority Magazine: Celebrity Matchmaker & Relationship Expert Bonnie Winston On Why Jennifer Aniston Has The Right Attitude When It Comes To Dating After A Divorce

There are challenges when regular people or what I call “civilians” are with people that are well known. Celebrities get stopped all the time and get asked for photo ops and autographs. Their significant others need to be patient and accept this as a way of life. Some challenges that someone “normal” may experience is that they may not understand her demanding schedule of shooting such as waking up early or traveling when filming, and attending award shows and events often. Being an actor is not just about acting, there are many more public relations opportunities they must handle.

Hollywood Life: Dating Your Coworker? How It Could Work, Like Cole Sprouse and Lili Reinhardt

If you and your coworker strike up a connection and decide to date, it doesn’t necessarily mean it’s doomed to fail just because it’s an office romance. Take Cole Sprouse, 26, and Lili Reinhart, 22, for instance – the Riverdale stars have mirrored their on-screen coupling between characters Betty Cooper and Jughead Jones in real life by initiating a relationship off-screen, too. While the couple has been pretty low-key, it’s clear they’ve found a way to be in a thriving relationship while working together for three years. We spoke to a couple of experts about how to successfully date your coworker, and celebrity matchmaker and relationship expert Bonnie Winston told HollywoodLife EXCLUSIVELY that since jobs nowadays go beyond the typical 9-5, and oftentimes work events go into personal time, she thinks “people should take ANY opportunity when it comes to love.”

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New York Post: These Couples Conquered Financial Stress -- And You Can, Too

Role Play

Bonnie Winston, 54, and her husband Ken Sugarman, 63, have a more old-fashioned approach to managing their finances, and that suits Winston just fine.

“He is the ‘boss of the budget,’ but I am the boss on how to spend it,” says Winston, a 54-year-old matchmaker who lives in Noho. “He decides how much we can spend on a vacation, and then I’m the one who chooses where to go.”

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Elite Daily: How to Feel Comfortable On a First Date

3. Download A Safety App On Your Phone

Matchmaker and relationship expert Bonnie Winston advises her clients and friends to download smartphone apps for their safety, since even dates that start out well "can turn weird quickly." 

At any point you start to feel uncomfortable, Winston tells Elite Daily, you can turn on one of these apps and have a subtle, but authentic-sounding excuse to leave. For example, the app uSafeUS has a feature called “time to leave,” which sends an urgent fake phone call or text from your parents or roommate, such as "I AM LOCKED OUT, COME LET ME IN."

These apps can definitely provide you with a good fallback excuse if you find yourself having trouble leaving on your own. 

Forward: Avoid These Smartphone Faux Pas On Your Next Date: Tips From a Celebrity Matchmaker

Sometimes in order to really connect with someone you need to disconnect…literally.

As a matchmaker, I’m charged with finding love for my clients, so they don’t have to swipe right forever. However, often I hear my clients complaining about people who are completely distracted while dating, making it harder for love to happen.

Here’s what you can do to avoid smartphone faux pas:

1) Don’t check the phone obsessively. Have you ever been with someone when they obviously check out another woman or guy that walks by? Looking at your phone all the time can make your date insecure and make them feel that they are not interesting or “enough” for you. Stop the constant glancing.

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StyleCaster: 9 Old-Fashioned Dating Rituals It’s Officially Time to Bring Back

“Chatting” on the Phone

It’s hard to believe that phone conversations are considered “old-fashioned,” but the reality is that many daters learn more about each other from texting and social media than they do from actually talking to each other. “Using your phone to make a personal connection shows a lot more effort than merely texting,” says celebrity matchmaker and relationship expert Bonnie Winston. “Studies have shown that hearing a loved one’s voice can increase serotonin levels. I tell my clients ‘ring instead of a ping’ when asking someone out.  It may be old fashioned but it works better, because it shows you care a little more.”

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Redbook: 21 Relationship Resolutions to Make in the New Year

“I WILL RENEW MY VOWS.”

You don’t need a big party or even an officiant to renew your commitment to each other. Rather, it’s about remembering the promises you made and the love you felt that day, says Bonnie Winston, matchmaker and relationship expert. “Get out your old vows or write some new ones and recite them together for a special bond,” she says. “You can also play your special song that you danced to at your wedding or eat the same type of cake you served. This is a good resolution because it brings back the romantic feelings.”

YourTango: If He Does These 5 Things, He's Not Chivalrous — He's Manipulative

5. He gets rough when you don’t play your part. 

This is the ultimate sign of false chivalry. Matchmaker Bonnie Winston shared with me that she had a female client who found a man who obsessed with one small thing: he absolutely insisted on walking next to the curb for “her safety.” 

“At first she didn't mind, but if she forgot and walked on the wrong side he’d yell at her,” explains Winston. “They broke up because one night on their way to dinner he put his hands on her, and pushed her away from the curb and she fell.” 

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Prevention: 6 Fresh Date Night Ideas For Couples Who Have Already Done Everything Together

Camp out in your home.

Feeling a little cash-strapped? Sometimes a great date doesn't have to cost a lot—or take you farther than your living room. "Set up a romantic indoor tent featuring your favorite comfort food, whether it's popcorn or paté. Set the mood with flameless candles (for safety) or a string of holiday lights and watch your favorite movie or show,” suggests Bonnie Winston, a celebrity matchmaker and relationship expert.

Romper: 23 Unexpected Questions That’ll Deepen Your Bond With Your Partner

"Do You Have An Endgame Goal?"

You need to know what your partner's goals are. Does he want to start his own company? Does she want kids (or more kids)? Are they thinking about goals for the relationship at all? Matchmaker and relationship expert Bonnie Winston says that you need to know what those relationship goals are. It's important for many reasons, but one of those reasons is that knowing that the two of you have shared goals for your relationship is one way to strengthen the bond between the two of you. Not knowing where the other person stands is never comforting.

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Bustle: 7 Ways To Know If Your Chemistry With Your Partner Will Last

7. Your Partner Makes You Laugh

Laughter can make for some great chemistry (and some lighthearted fun, of course.) "Chemistry can peter out quickly, but if your partner makes you laugh, or you do other chores together and adore one another OUTSIDE of the bedroom as well as inside, those are clues that your partner and your passion will not fizzle out," says celebrity matchmaker and relationship expert, Bonnie Winston, over email with Bustle. 

If you have any of these habits and behaviors in your personal relationship, you're in luck. There's tons of promise that you and your SO will stay happy and intimate for years to come. (Which is what everyone wants, right?)