The Scoop: As both a Matchmaker and Dating Coach, Bonnie Winston wants her clients to be on their best behavior — especially on a first date. That can mean not ordering expensive dinners or talking too aggressively about politics. While she gives her clients plenty of tough love, her coaching mission is to help singles find the long-term relationships and marriages they seek. Bonnie’s commitment to that mission is evident in her ever-expanding list of clients and partnerships with matchmakers and dating coaches across the country.

Matchmaker and Dating Coach Bonnie Winston, who works in New York and Los Angeles, said she understands that some of her clients are diamonds in the rough. They may not have the dating experience to impress a potential partner, or they may be unaware of the behaviors they display that turn dates off. But she helps them polish their dating habits.

Bonnie shared the story of a female client who hadn’t had a boyfriend in many years. On the first date Bonnie set up for her, the woman ordered an expensive lobster dinner, dessert, and several drinks. Meanwhile, she told stories about herself and didn’t ask her date any questions.

“Of course, he didn’t like her,” Bonnie said with a laugh. “After that, I owed him because I wanted him to trust me to set him up with other people.”

In her line of work, Bonnie said she finds that some daters don’t just need to be paired with the partners of their dreams, but they also need guidance on how to behave appropriately. One recent trend that she’s seen that turns off potential partners is too much talk about politics. Few of her clients are willing to date people on the opposite side of the political aisle.

Screenshot of the Bonnie Winston motto
Bonnie Winston’s motto, “I Find Mates, Not Just Dates,” echoes her commitment to long-term love.

“Years ago, people didn’t talk about politics so much unless they were zealots,” she said. “When I grew up, you didn’t talk about sex, religion, or politics. But now it’s something I have to include on my client intake form.”

Keeping up with those trends is essential to her job, which she views as an investment that singles can make that’s on par with an education.

“When you invest in your education, you become more intelligent and receive a diploma and have a chance to get a better job,” Bonnie said. “When you invest in a matchmaker, the potential payoff is a husband, marriage, true love, and even a baby, if you want that. “

Bonnie goes beyond picking compatible matches. She also teaches clients how to take the next steps in presenting themselves and developing real connections.

Dating Coaching Helps Improve a Client’s Appeal

Bonnie shared two examples with us that prove successful matchmaking isn’t just about setting two compatible singles up on a date — it’s also about how both parties behave on that first date. If one of her clients doesn’t make a great first impression, though, Bonnie works with them to get it right.

One of Bonnie’s tips is to keep pace with your date on a first date. Don’t order considerably more than your date does at the restaurant or bar; otherwise, the person who is paying may feel taken advantage of.

Furthermore, Bonnie suggests her clients show class whenever possible. She tells her client to extend the same kindness to the waiter or busboy that they would extend to their date.

“Class is just being kind. If you’re kind, it shows, and people are attracted to it,” she said.

Photo of mixed race tourist enjoy lively communication, discuss traditions of their countries, eat fastfood on street, being in good mood. Beautiful Afro American girl talks with handsome guy outdoor
Working with a dating coach can help you become a more attractive partner.

She also shared advice she gave to her lobster-ordering client for a more successful date with a different man.

“Ask questions, but don’t interrogate. The best way to learn is to listen, so ask your date things about themselves,” Bonnie told the client.

Bonnie said she thinks some daters have an unrealistic perception of themselves and the reasons why they’re still single. Some are right about the reasons why they’re single. Others have inflated views of their power, success, or intelligence that get in the way of forming successful bonds with others.

“People should trust a matchmaker because that’s where they can get an unbiased opinion,” she said.

Those living outside of New York and Los Angeles who are interested in Bonnie’s advice can read her blog, which is updated regularly. She offers many of the same tips she imparts to clients through posts, including “What is Matebaiting?” and “Tired of Tinder?”

Creating Safety and Comfort for Women in the #MeToo Era

Bonnie said she wants to create a safe atmosphere in the #MeToo era for her clients, many of whom are women in Los Angeles. She sets parameters that create comfortable first dates for both parties. For example, her daters can’t meet in private places — including a hotel or someone’s home — on the first date.

“I put all those things in the contract to protect women who are my clients. Today, you have to be more thoughtful,” Bonnie said.

Photo of Bonnie Winston, Matchmaker and Dating Coach
Bonnie coaches her clients to show the best version of themselves — especially on first dates.

Since many prominent men have been called out for their inappropriate behavior, some of her male clients are nervous about how to behave around women. Bonnie offers them advice on how to behave appropriately around women.

“If you have to double-think it, just be conservative,” she said. “If you ask yourself, ‘What do I do here?’ Then don’t do anything.”

Still, men shouldn’t be so nervous about offending women that they never make the first move. They still need to be able to read signals. Otherwise, Bonnie said, they may be friend-zoned early in what otherwise could turn into a long-lasting relationship.

One of her clients, a successful cardiologist, went on two successful dates with a woman he liked. When Bonnie checked in with her client about the proposed third date, he told her how nervous he was about kissing her for the first time.

“I said, ‘Do me a favor and just lean in. You need to do this sometime during the third date.’ There are times I have to tell grown men to kiss their dates. Don’t grope her, but let her know you like her.”

The cardiologist’s date turned into a love story when he took Bonnie’s advice and kissed the woman on their third date. The two are still happily together.

Bonnie Winston is Developing a Nationwide Network of Singles & Matchmakers

While Bonnie wants to help people find love, she knows she can’t help everyone. Most of her clients live in New York and Los Angeles, but she is adding more clients in Florida and Seattle, as well. But she wants to encourage love through other matchmaking professionals and coaches outside of those areas.

“I’m now connected with 200 coaches and matchmakers, and I value those relationships because I think there’s a lot of love in the world,” said Bonnie.

And those connections aren’t just superficial. Bonnie spends at least one day a week in communication with others in the field. Sometimes, they share clients whom they can’t match with their current dating pools.

“I don’t look at as competition, but as working together to find what is best for the client,” Bonnie said.

Certainly, Bonnie’s client list is ever-expanding because she’s a New Yorker unafraid to assert herself. She regularly introduces herself to anyone who’s not wearing a wedding ring.

“If daters aren’t acting appropriately, they’re going to blow it. That’s why I not only introduce people but also teach them how to present themselves well.” — Bonnie Winston

“I just took an Uber Ride Share with a man and a woman. Now, I’m fixing the woman up with someone I know,” she said. “And the guy, I’m going to put him in my database because he’s adorable. I would send him to another matchmaker who needs someone who is 30 and has a good job.”

This eagerness to network and find new matches for her clients demonstrates Bonnie’s dedication to her mission: helping her clients find “mates, not just dates.”

Bonnie accomplishes much of that mission through her drive to find new clients, but she can’t make these mates without the help of the daters themselves.

“If daters aren’t acting appropriately, they’re going to blow it. That’s why I not only introduce people but also teach them how to present themselves well,” she said.

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