Cara Matchmaking Helps Singles Take Calculated Risks

Women's Dating

Cara Matchmaking Encourages Singles to Take Calculated Risks and Reap Romantic Rewards

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at DatingAdvice.com. When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating expert. As an English major in college, Amber honed her communication skills to write clearly, knowledgeably, and passionately about a variety of subjects. Now with over 1,600 lifestyle articles to her name, Amber brings her tireless wit and relatable experiences to DatingAdvice.com.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles and reports have been edited for overall clarity, accuracy, and reader engagement.

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The Short Version: The loneliness of the COVID-19 pandemic made many singles want to search for a partner with whom they could build a life. But finding love isn’t always easy, and singles need to get out of their comfort zones to connect with others. Noreen Rochester and Julianna Acheson of Cara Matchmaking share their advice on planning ideal first and second dates and explain why matchmaking can be so much more effective than online dating.

Singles may struggle to get outside their comfort zones when looking for love. Perhaps they aren’t happy with their dating profile, but they’re comfortable enough to keep it. Or maybe they keep attracting the same kind of person, but they’re nervous about seeking a new way to meet others.

That is why it’s so important for singles to take calculated risks, without which they would repeat the same patterns that haven’t paid off.

Matchmakers Noreen Rochester and Julianna Acheson argue that risk-taking is imperative when looking for love. And they help singles take those chances through Cara Matchmaking, a firm that has helped singles find love for 25 years.

“Everybody is nervous. Everyone’s hand shakes on the doorknob. Nobody knows — it’s always a mystery, and you need to embrace the risk and mystery because life is short, and if there’s nothing risked, there’s nothing gained,” said Noreen.

Photo of Noreen Rochester walking on the beach with her dog
Noreen Rochester offers advice for singles who want to ditch online dating and hire a matchmaker.

Psychologist Rochelle Perper, Ph.D. agrees that taking risks when searching for a meaningful relationship has its benefits.

“The ability to take calculated risks is actually an essential human trait, crucial to our development as a species and as individuals. Our risk-taking ancestors were the survivors, the daring ones who took chances to adapt to a changing environment. Today, the same principle applies: in order to grow, we need to experience challenges and take risks,” she said.

If someone is nervous about taking a chance on something that scares them, she recommends they start by taking a small risk. Perhaps an anxious dater can spend time alone in a coffee shop with the goal of talking to one person. Or someone who feels deterred by dating apps can initiate one conversation per day.

“The experience will show you something special about life regardless of what happened yesterday or what might happen tomorrow,” wrote Rochelle.

Creating Ideal First and Second Dates

Noreen and Julianna know what they’re talking about regarding love. Noreen is the Founder of Cara Matchmaking, and Julianna is one of the team’s matchmakers, a cultural anthropologist, and an online dating expert. Her book “Twenty-Five Cups of Coffee: Mastering On-Line Dating” describes her experiences on 25 dates in Portland, Maine.

The synopsis of her book reads:

“After finding herself divorced and trying to meet a new man, she found herself using her anthropological skills to analyze her dates. Convinced that she would not be able to sort out prospective dates without meeting them, her strategy consisted of having a simple cup of coffee with twenty-five men.”

Noreen and Julianna certainly have plenty of experience and offer good advice for singles who are just starting to seek a relationship with someone.

The Cara Matchmaking logo
Cara Matchmaking helps clients make the most of their first dates.

Here are two things they say to avoid: first-date dinners and a belief that first dates are strong indicators of compatibility.

Julianna suggests that long first dates can be a nerve-wracking introduction when going out with someone new, so singles should choose alternative ways of meeting a first-time date.

“Plan for an hour or two, take a walk. Anybody is going to feel uncomfortable for more than six hours. It’s a new person and situation. Don’t dive right in. Go slowly. Go lukewarm and see where it goes,” she told us.

Both matchmakers recommend that singles not take the first date too seriously. First impressions can be wrong, so daters should instead keep a simple idea in mind regarding that first in-person encounter: getting to know this person better.

“People aren’t themselves. They’re not comfortable on a first date, so I think a second date is a good idea just so everyone is more comfortable after the first one,” Noreen said.

Matchmakers Foster Many Romantic Successes

Noreen, Julianna, and the rest of the Cara Matchmaking team have witnessed many success stories through the years. Now, they have a better idea of what makes an ideal first date.

Doing something on a first date that both singles enjoy is a good start, Noreen and Julianna said. For example, if the couple both like bowling, they can go with that.

Even a walk on the beach — a romantic cliché — is a good idea because it provides a nice distraction from the dating process. When singles sit across a table and stare at each other on a first date, it can feel like an interview.

“I had a new client recently, and her first date was her only one because she fell in love and got married a couple of months ago,” Noreen told us. “They played nine holes of golf. That was a long date, but it was a great date because it was something they both loved.”

Screenshot from Cara Matchmaking website
Cara Matchmaking offers members a more bespoke experience than online dating sites.

First-date conversations are also crucial in developing a lasting connection. Singles should avoid talking too much about themselves and ask the other person plenty of questions.

“Try to find some common ground and topics that are fun and interesting and ask them questions that make it more interesting. Engage the other person,” said Julianna.

Most successful couples don’t end the first date with a kiss because it’s too soon in the relationship. A peck on the cheek, a handshake, or a hug is usually more appropriate.

Etiquette on the first date is also important.

“People go on a date, and when the check comes, if one person doesn’t offer to pay or tip or say ‘thank you,’ that’s not positive feedback,” Julianna said.

Step Out of Your Comfort Zone for Love

Singles can have good first and second dates on their own, but connecting with a matchmaker can improve your chances of finding success. Cara Matchmaking can offer clients a better experience than online dating, where users often ghost each other with no explanation.

Matchmaker-led dates are also typically more successful because matchmakers get both sides of the story. They can then provide clients with the feedback they need to have a better second date or make a stronger first impression on their next date.

“I’ve got their version, and I’ll get your version, and we learn more about a person from feedback after a date than a two-hour interview. I never want to hurt anyone’s feelings, and it’s a scary and exciting process. It’s all done kindly and gently with love. We’re deliberate with our feedback,” Noreen said.

If singles can’t hire a matchmaker, Julianna suggests they research dating advice techniques, including safety recommendations while on a date.

“Use a great matchmaker if you can, but if you can’t afford to, be safe, be smart, trust your gut, and there are some precautionary measures, like don’t meet alone in the dark,” Julianna said.

Singles should put their best foot forward by planning an idyllic date and preparing questions. But the most essential element in finding love is bravery. Singles will never know what they’re missing if they keep doing what hasn’t worked for them in the past.

“Have a way to leave but take a risk. It’s a challenge. You never know when you’re going to find that person, and it’s a blessing to have a wonderful person around to talk to,” said Julianna.