Appeared on BESTLIFE: The 20 Questions You Should Never Ask On a First Date




'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.” Even when you’re in a relationship, if you have separate finances you shouldn’t feel obligated to tell your partner the price of something you spend your own money on—in fact, it’s one of the 13 secrets you should always keep from your partner."


Original article: The 20 Questions You Should Never Ask On a First Date originally published on BESTLIFE

Appeared on Bustle: What Is Dating Imposter Syndrome? If You Feel Like You Don't Deserve Your Partner, Listen Up

"I have a client who, despite the external evidence that she is drop dead gorgeous, believes herself to be a fraud who does not deserve the men she always attracts," Celebrity Matchmaker and Relationship Expert Bonnie Winston tells Bustle. "She once remarked that a man I fixed her up with must be 'vision impaired' to have been attracted to her and liked her. She also said it was 'just good timing.'

Original Article:   What Is Dating Imposter Syndrome? If You Feel Like You Don't Deserve Your Partner, Listen Up published on


Appeared on Brit +Co: 8 Ways to Make Time for Romance No Matter How Busy You Are

3. Connect in spite of distance and busy schedules. We understand how life can be — you’re

traveling every week for work and your partner always seems to have work events on the nights you’re actually home, or you’ve just been ships passing in the night lately because of your entirely opposite (yet equally cluttered) social calendars. Is there ever an end to the chaos? Not really, which is why it’s important to learn to work around the limitations of time and space. You can still connect with your S.O. and create that spark when you’re separated! For couples dealing with a difficult travel schedule, matchmaker and relationship expert Bonnie Winston suggests choosing a book and taking turns reading chapters to each other over the phone each night, which will build a nightly routine around intimacy, instead of just watching TV alone. Similarly, licensed marriage and family therapist Rajani Venkatramanencourages busy couples to keep romance going with small gestures. “Romance and passion do not rely on constant physical presence,” she says. “In fact, they thrive quite well on the gaps between connection, as long as we keep the connection well fed. Leave your lover a note tucked in the cereal box, a heart drawn on the misty bathroom mirror, a sexy goodbye kiss as a promise of more.”

Original Article from Brit + Co 8 Ways to Make Time for Romance No Matter How Busy You Are

Appeared on Bustle: 11 Subtle Signs Someone Is Probably Flirting With You, Even If You Don't Think So

It seems like such a simple thing, but a person with a crush will a) always hear what you say and b) make an effort to show their appreciation. So, if this potential partner is always responding to you with a laugh or a smile, take note. As matchmaker Bonnie Winston says, "If they giggle at your jokes, that may be a subtle way of flirting."

While not necessarily classic signs of flirting, these little gestures are still the real deal. And, they might even mean that nervous, slightly standoffish person is actually totally into you.  


Original Article:  11 Subtle Signs Someone Is Probably Flirting With You, Even If You Don't Think So published on Bustle

Appeared on Mental Floss



Whether they’re shopping for groceries, waiting in a doctor’s office, or traveling on vacation, matchmakers always have their eyes peeled for ideal partners for their clients. “Being a matchmaker is not a 9 to 5 job,” matchmaker and dating coach Bonnie Winston tells Mental Floss. “24 hours, seven days a week is more like it. My employees go home, but I never close!”

Winston, who often works on weekends and evenings, also gives her clients dating advice before, during, and after dates. “It is not unusual that clients call me with inquiries about what they should wear before certain dates,” she says. “Or, I’ll get calls in whispered hush tones—secretly from bathrooms in dining establishments—to ask me questions on etiquette, or if they can hook up with their date because they have great chemistry,” Winston says.


Romance is mysterious—no one can predict whether two strangers will meet and fall in love. But successful matchmakers possess a high level of emotional intelligence and intuition that guides them in their work. Winston, who made her first successful match when she was 16 years old, says she just has a natural sense of which people would be good together. “Matchmaking isn’t something that can be bought or taught,” she says. “I will meet someone and just know when they are a good match for one of my clients.”


Besides speaking with people they encounter in daily life, matchmakers may also rely on their networks of family and friends. “My mother is one of eight siblings and I have literally dozens of cousins who are well aware that there is a ‘yenta’ in the family. I tap into those resources, too!” Winston says.


Clients may also have emotional blocks that get in the way of finding love. “Some people say they want to get married but they don’t really want to,” Winston says. “They turn down every potential date for a ridiculous amount of petty and inconsequential reasons.”



Dating apps give people a huge number of potential matches at their fingertips, but most apps don't vet matches—and good results are not guaranteed. “[Dating apps] make things so impersonal,” Winston says. “[Users] are deleting really good people forever so easily in seconds with their fingertips. And scratching their heads [about] why they can’t meet anyone.”



While apps may be many people’s initial foray into the dating world, a disappointing experience can lead unsuccessful daters to a matchmaker. “Honestly I think [dating apps] impact [our industry] positively,” Rose says. “People who try those apps or sites see that they are about quantity not quality, and then they research better options and find me.” Winston adds that matchmakers slow down the online dating process. “People who come to me are sick of swiping, scrolling, sexting and texting, getting poked, and being ghosted. They are burnt out,” she says. “I bring back old-fashioned courtship and romance.”



Visuals and first impressions play a huge role in dating, and good matchmakers help their clients improve their image. “You’d be surprised how many people come to me with terrible selfies to find love!” Winston exclaims. Because she owned a fashion photography agency, Winston stays connected to top photographers and hair and make-up artists, and she provides her clients with professional photo shoots. “I want my clients look their best while showing their authentic selves,” she says.



When matchmakers succeed in bringing two people together, they’re ecstatic. “I am joyful when my clients find joy in love. Especially when they immediately 'click'—I feel like I hit it out of the ballpark ... a homerun!” Winston says.

Original Article: 11 Secrets of Matchmakers published on Mental Floss

Appeared on Bustle

"It's expensive to go out to dinner, so I totally understand why that might not a possibility every week, or even every month. But if you're ordering in every night and then eating on the couch, it might just mean laziness has set in. "Don’t wait for an anniversary to put some spark back into things," says Bonnie Winston, a NYC-based celebrity matchmaker and relationship expert. "Try getting dressed up and going out for a date night instead." Even if it just means walking around the park."


"The best part of a relationship is getting to that stage where you can be super comfortable with each other. Be careful, though, because this can be a slippery slope into a passionless situation. As Winston tells me, there's always room for a little lingerie or whatever else makes you feel sexy, all in the name of reigniting that spark."


"We all need to veg out, and that's OK. But things can get pretty damn stale if you both make a habit of staring into the TV without acknowledging each other. As Winston says, the lack of interaction during a TV binge can be a sign of a lack of passion. So make an effort to spice things up. "Try going out to a show," she says. "Or an activity where you can interact and share opinions."

Original Article: 11 Daily Habits That Indicate There's No Passion Left in a Relationship  published on Bustle

Appeared on Bustle

Skip the internet stalking and be upfront about past relationships. Ask about any exes who might still be in your partner's life. "It's necessary because you want to go in knowing the score about others — is there a possibility they are still involved?" says matchmaker Bonnie Winston over email.

Original Article: 7 "Uncomfortable" Questions All Partners Should Ask Each Other Anyway published on Bustle

source: PEXELS

source: PEXELS

Appeared on Women's Health,

"The good news? Chances are you have seen that person in their natural, authentic state, says dating coach and matchmaker Bonnie Winston—since you've seen how they act as they handle pressure, deadlines, and responsibilities. What happens under those fluorescent office lights makes it a lot easier to see someone clearly than when the lights are dim over a glass of wine."

"...Law firms are also typically against interoffice relationships, Winston says."

Original Article:  Questions To Ask Yourself Before Dating A Coworker published on Women's Health and


Appeared on Business Insider & The Independent

"Sociopaths are sometimes terminally unemployed. They can't seem to hold down a job because of their attitudes and will blame it on everyone but themselves. 

"They are so antisocial they burn their bridges at work and blame everyone else but themselves for their inability to succeed," relationship coach and matchmaker Bonnie Winston told INSIDER."


Original article: 13 signs that you're dating a sociopath published on Business Insider and The Independent

Appeared on

I'm sitting across from Bonnie Winston at Balthazar, a swanky SoHo bistro in Manhattan. We're eating hard-boiled eggs and talking about love. And how much it costs to find it. Don't send a check.
Send cash by e-mail
with just a click.

Winston, a 40-ish blonde, is the head of Winston West, a successful photo agency with offices in New York and Beverly Hills. But that's not her passion. "I've always been a matchmaker," she says. "I've been fixing up my friends for 20 years."

Winston -- who claims to have helped set up Kevin Kline and Phoebe Cates -- says that she's so good at what she does that she has decided to launch a small matchmaking business on the side. "I just see so much money in it, to be honest," Winston told me earlier on the phone. "Men and women will pay anything to meet the right person."

She's not kidding. While Winston is charging a hefty $ 15,000 as her finder’s fee, elite matchmakers command fees that can range from $10,000 to $200,000. When my friend Wendy, a fellow single gal, heard this, she was stunned. "I paid thirty bucks to go to a Date Bait singles event at the 92nd Street Y," she says. "I want to know what these women get for $15,000."

It ain't personal, it's business
Nobody likes to couch a topic as delicate as love in the crass terms of finance, but the fact is that few things will have more of an impact on your financial future, lifestyle and standard of living than whom you choose to marry. Should the partnership fail, the financial consequences are also heavy. Men stand to lose half their assets. Women, especially if they have children or have left the workforce to raise those children, can lose that much and often more.

As a 36-year-old woman who is both single and self-sufficient, I think about this a lot. A few years ago, a friend of mine passed along some advice her mother had given to her: "It's just as easy to fall in love with a rich man as a poor man." Hopeless romantic that I am, I was horrified. Meanwhile, my friend married a guy with a trust fund and a sizable inheritance looming on their now-shared horizon.

That doesn't mean I could ever shift my values and go fortune hunting, but as your no-longer-innocent personal-finance columnist, I can't pretend that love doesn't also have a bottom line. 

. . . Especially now that I know what these matchmakers are charging.

Maria Mancini Matchmaker, who covers the Philadelphia-Delaware area, charges $995 for a six-month membership, which includes at least six "introductions" (as they're called in the biz). For an exclusive search, i.e., finding you a match outside her private database, her price goes up to $5,000. 

Moving on up, for a mere $10,000 you could retain the services of New York-based Janis Spindel, head of Janis Spindel Serious Matchmaking, and get six introductions a year for the most basic membership. For $15,000, you get 12 introductions and "Preferred" status.

Or, if money really is no object, there's Selective Search in Chicago. Selective Search, which also recently opened offices in New York and San Francisco, charges a yearly retainer fee of $15,000 to $25,000. 

Or go for broke -- literally -- with Beverly Hills-based Orly. She'll nail you for up to $200,000 "depending on geographic location and desired selection criteria."

It doesn't take a genius to realize that the steeper the entry fee, the more well-heeled the clients are likely to be . . . unless they're in hock up to their eyeballs.

Take a page from Jane Austen
But let's face it: Love is an investment. Once upon a time, this was discussed openly. Marriage was created largely to secure property, power and other assets. Pick a Jane Austen novel -- any Jane Austen novel. Or just read the opening line of "Pride and Prejudice":

"It is a truth universally acknowledged that a man in possession of a good fortune must be in want of a wife."

And for those in want of a partner, someone in possession of a good fortune might not be a bad idea. Why would anybody pay a matchmaker tens of thousands of dollars, except to gain access to a certain class of people who don't want to just hook up with some shmoe in a bar?

"Time constraints," says Barbie Adler, head of Selective Search in Chicago, naming the No. 1 reason most matchmakers say their clients come to them. Tied for second are a) their clients are tired of bars and parties (translation: they didn't meet anyone there) and b) they've struck out everywhere else.

Money as a motive is rarely acknowledged, except indirectly. "When people pay for a membership, they know they are going to meet people who have made the same commitment," says Maria Mancini, head of Maria Mancini Matchmaking. "They want to meet someone who has more to offer -- and not just financially."

All they want is love. Really.
I've paid my dating dues, and I do believe that the appeal of these services isn't just the potential return on a cash investment. Dating is dirty work sometimes. We pay financial pros to make tough decisions about our money for us, so why not seek the expertise of someone who can simplify our love lives?

Still, you can't take money out of the mix. When Winston met with her first client last week, a 40-year-old investment banker, the woman confessed that no one had ever set her up on a date. Winston was sympathetic. "I told her that no one ever set me up on a date either, and that's why I started doing this. Everyone wants the same thing: to find someone to love."

Her client agreed, and added that if Winston knew any bankers, that would be all right, too. 

"I don't think the women who are coming to me want to meet a starving artist," Winston says, with a refreshing candor. "They want a provider. And I feel bad because, in my photography business, I represent a lot of starving artists -- and they're great guys."

I'm sure they are. Meanwhile, Winston says she has the perfect guy for me. "He's 38, he went to Yale, and he publishes his own magazine," she says. "I met him at my hair salon. . . ."

New York Observer

Kenneth Sugarman and Bonnie Winston

Met: Memorial Day weekend, 2001

Engaged: Dec. 13, 2001

Projected Wedding Date: May 11, 2002

By day, Bonnie Winston runs Winston West, a glamorous bicoastal photo agency that represents fashion and celebrity photographers. By night-she’s a yenta !

Everywhere she goes, Ms. Winston who is blond and bubbly, keeps a running tab of her friends’ and acquaintances’ vital statistics, scribbling them down in a little red appointment book.

“I talk to everybody ,” she said. Recently, she bragged, she sidled up to Sex and the City actor John Corbett at a bar and hooked him up with a work pal of hers, a fashion model named Krista Cassidy.

Last Memorial Day weekend, a friend of Ms. Winston’s dragged her out to East Hampton, hoping to get a piece of that matchmaking action. They went to a place called the Grill. “My whole theory is, go somewhere that used to be trendy,” said Ms. Winston. She was munching on a cheeseburger and fries when she glanced to her left and noticed an attractive older man in sweat pants and loafers, sipping a white-wine spritzer.

“How about that guy?” she asked her friend.

“Why don’t you like him?” her friend asked.

“He’s a little Robert Blake–ish,” she said, “and my name is Bonnie.”

But she struck up a conversation nonetheless and learned that his name was Kenneth Sugarman, that he was a perfectly respectable general-practice lawyer specializing in civil litigation, and that he was in the Hamptons helping his daughter from a first marriage celebrate her graduation from Manhattan’s Trinity School.

When they met the following Thursday at Balthazar, Ms. Winston was pleasantly surprised.

“He really cleaned up well,” she said. “I thought him more Robert Downey Jr. than Baretta.”

Make that Mike Brady: Mr. Sugarman, a lawyer told her almost immediately that he wanted to remarry and have more kids. Phew .

Months later, the pair was snuggling together in his Noho loft, watching the final round of Jeopardy . The category was U.S. Presidents. “This man,” said Alex Trebek on the TV, “was elected Vice President twice and President twice.”

Naturally, it was at this moment that Mr. Sugarman turned to Ms. Winston and proposed.

Her response: “Yes! Nixon!”

(Hey, she forgot to put it in the form of a question!)

“I never get Final Jeopardy right, so I look at it as a sign,” she said. “I was so excited that I knew the answer that I couldn’t let it go. I’m a really big multi-tasker.”

That same night, she set up two close friends and they all went out on a double date.

– Blair Golson