The Scoop: Singles often need a wingman or wingwoman to help them feel confident when they approach someone they find attractive. Cher Gopman founded NYC Wingwoman to take that concept a bit further for singles in the Big Apple by offering one-on-one coaching and guidance on how to land a date. The firm also offers an intensive weekend bootcamp featuring numerous dating professionals who specialize in areas of communication and relationships. All of NYC Wingwoman’s services aim to help clients feel prepared whenever they meet that next special someone.

In the depths of Craigslist’s online classifieds page, there is a section called Missed Connections. That space allows those who may have been too shy or flustered to introduce themselves in real life to make one last effort to connect with someone they crossed paths with. That could be the anonymous woman walking her poodle, a man wearing a red shirt in the bookstore, or a barista who smiled at them.

Of course, most missed connections never end up finding each other, and that’s one reason why Cher Gopman, Founder of NYC Wingwoman, started her date coaching business.

The NYC Wingwoman logo

NYC Wingwoman prepares clients to interact with potential partners when the opportunities arise.

“We never want anyone to see someone they’re attracted to and not know what to say,” she said. “We never want them second-guessing themselves. We want them always to be ready and to live in the present.”

In the modern dating world, many singles rely on apps to present potential partners who may be interested in them. But those connections aren’t a sure thing, and sometimes they don’t result in lasting love. That’s why it’s crucial to be prepared to make a connection whenever and wherever an opportunity arises.

The coaches at NYC Wingwoman understand that’s not easy for those who lack experience or success when it comes to dating. When someone lacks confidence in their communication skills or other elements of social interactions, it’s often more comfortable to shy away from casual conversations — especially if the other person is attractive.

That’s why Cher assembled a team of specialized professionals to offer one-on-one coaching for singles.

“Our whole goal is to help people enjoy dating,” she said. “It shouldn’t be a scary thing. It should be fun and enjoyable.”

Founder Cher Gopman Saw That Relationship Issues Led to Anxiety and Depression

Before launching NYC Wingwoman, Cher worked as a registered psychiatric nurse. She noticed that a lot of patients who were in crisis suffered from anxiety and depression due to bad relationships. That’s when she realized that she wanted to help people find happy, healthy relationships at times when they weren’t in a state of crisis.

Cher also recognized that she had become the go-to person for her friends who had questions about how to deal with dates or their romantic relationships. So, she decided to become certified as a life coach. After earning her certification, the calls asking for help soon grew, and relationship coaching became her full-time job.

Now, with NYC Wingwoman, she works with a large team of professionals to help men and women gain the confidence and skills they need to succeed in dating. She said she works primarily with successful professional men who have careers in finance, engineering, and medicine, and range in age between 25 and 45.

Initially, she created a program that was simply one-on-one coaching that would take place whenever the client was available. But then, she developed a specific methodology that allows all her clients to get direct, individualized feedback from her entire team through an intensive process.

“We have a full weekend program, and people fly in from all over, or they live in New York City,” she said. “I realized after I began that people don’t grow as much unless they are immersed in change. So I revamped the whole program, and I’ve gotten so much positive feedback. And clients really notice that change.”

A Team of Professionals Provides Feedback Throughout the Entire Process

Cher’s bootcamp takes place over a single weekend, so her clients don’t have to take time off work. And it’s intense, she said.

First, clients begin with a Skype session with Coach David, a former client himself, who has been working with Cher for three years. He can relate with the clients as he once suffered from anxiety regarding relationships.

But he shares his story about how he overcame his obstacles and gained the confidence to pursue people he was interested in. He gives an overview of the process and some much-needed reassurance and encouragement.

“We try to stay offline and in real life, so he is the person who is going to get you ready for the weekend. A lot of people we work with have a lot of anxiety when it comes to dating,” she said. “He works with them to get out of their heads. We call it a ‘Mastermind Session.’”

Photo of NYC Wingwoman Cher Gopman

Cher Gopman founded NYC Wingwoman to empower daters in the Big Apple.

Next, clients meet with a coach for a mock date. NYC Wingwoman tries to keep it as real a date as possible. After the date, the coach is revealed and offers honest feedback on how everything went. The goal is to shed some light on behaviors, communication traits, or other elements that could use improvement before the next date. Cher says the coach is “authentic and real, and gives it to them straight.”

The next day, the client meets with Coach Isabella. She’s a specialist in confidence and being present in the moment. She works with clients on exercises to understand how to start memorable and relaxed conversations in an easy, authentic way.

“It’s a little like improv. You have to take what you’ve got around you and go with it,” Cher said.

Clients then head to Coach Imad, who has worked with Cher for nearly four years. He gets them out on the streets of New York City and provides hands-on, real-life skills for talking to attractive people.

“We’re very against pickup lines,” Cher added. “We want honesty, so he uses what’s around you to be truthful without feeding them lines. The goal is to develop their own techniques and be confident when it comes to dating.”

Finally, the clients meet with Coach Candice, who is an online specialist. She examines the client’s online profile and provides tips on how to express themselves so they can have an enjoyable experience using dating apps or sites.

NYC Wingwoman: Helping Clients Feel Confident and Ready for Love

NYC Wingwoman is on a mission to ensure that its clients don’t miss any connections — whether online or in the real world. Cher said the team frequently communicates and works together so the clients can benefit from their collaborative nature.

Because the work is so individualized, coaches feel like they’re going through the process along with the client.

“It’s a new journey, and clients don’t go on it by themselves. All the coaches, we feel like we’re a part of it with them,” Cher said. “When they’re excited, we’re excited. When they’re depressed about something, we get sad about it, too. It’s a very up and down emotional rollercoaster we go on with them, but we love it.”

And NYC Wingwoman has seen plenty of success stories, too. Cher said that she loves hearing from clients who were at one point very uncomfortable with dating, but later found the love of their lives.

“Love is the most precious thing in the world, and if I can play a role in helping people find that, I’m doing some great work,” Cher said. “I’m proud of what we do.”