‘If it’s meant to be it will blossom like a flower’



Ron Cater

The Matchmaker of Maine, Portland


For more than 30 years, Ron Cater has been helping men and women – about 90 percent of his clients are baby boomers – find love through his personalized matchmaking business.

“It’s interesting how the industry has evolved,” said Cater, 62. “Back in the day, in the ’80s, most of our members were in their late 20s, 30s and 40s.”

Cater has been running the 18-year-old Matchmaker of Maine company on Congress Street in Portland since 2005, when founders Tom and Noreen Rochester decided to sell it. Cater also owns several other locations in New Hampshire and Massachusetts.

“They contacted me and asked me if I was interested in taking over,” said Cater. “It’s a small market, but it’s great. I’ve really enjoyed working with the people in Maine.”

Cater said younger mate-seekers are turning to online dating sites rather than matchmakers.

“It’s a whole new world,” he said. “The younger folks are now using Match.com, Tinder, and are on their mobile devices meeting people.”

But dating doesn’t come as easy to divorced or widowed baby boomers, Cater said. That’s where his dating service comes in.

“Women especially, don’t find (online dating) particularly safe,” Cater said. “They find that a lot of people are less than honest in terms of how they represent themselves.”

Cater said Matchmaker of Maine is attractive to the baby boomer generation because “it’s a very safe and effective way” to meet genuine and honest people seeking a committed relationship. All of his clients are interviewed privately and undergo a personality test and criminal background check.

“That helps us better understand who the client is, what their personality is like, what their interests are, and ultimately, what their value system is and what kind of person will be a good fit for them,” Cater said. “It’s extremely discreet.”

According to Cater, a boomer likely hasn’t been on a date in years, and there aren’t many venues available other than a bar or nightclub for boomers to meet other single people in their age group.

“Being single is not easy. It’s tough out there, particularly tough if you’re a boomer,” said Cater, who lives in Massachusetts, but also has a home in Harpswell.

Cater, who is married and has a daughter in her 30s, recently took the time to chat with My Generation about how he got into the matchmaking business and the dating advice he has for baby boomers.

Q What inspired you to become a matchmaker?

A I wanted to help people find love, because I personally know how great it is to be in caring, loving relationship. Loneliness is no fun. It can be very depressing. Being with someone that you really connect with in a meaningful way is priceless.

Q What do boomers generally seek in a partner?

A I’m a baby boomer, and I love working with my members. They are a great group of people who find themselves single (sometimes not by choice) and we provide a very safe and effective way to meet other liked-minded singles.

Baby boomers know what didn’t work for them in previous relationships so they have experience to draw on. Most women would like to meet men that are healthy, honest, kind, and still like to do things. Financial stability is also important to most boomers. The men typically ask for someone in reasonably good shape, and someone that has the time and financial means to do things such as travel. Affection and romance are still important to most boomers.

Q What relationship challenges do boomers face?

A Baby boomers face some of the same relationship challenges that younger singles face, including how to meet people that are really single, available and sincerely interested in a committed relationship. At The Matchmaker, we provide a very easy and safe way to meet other singles without the game-playing often found on Internet dating sites.

Q How is helping someone in their 50s find a match different from someone in their 20s?

A Helping people in their 40s, 50s and 60s is certainly different from working with someone in their 20s. Most of our members have had their families and are now divorced or widowed. Some are near or at retirement age. They want to enjoy what time they have left, and live life to the fullest. Our members are in good health and are financially secure. They want to meet someone they could connect with and do things with. They don’t want to sit around getting old alone.

Q What is your advice for baby boomers who are getting married or plan to get remarried?

A Some boomers would like to re-marry, while others are perfectly happy having a committed relationship without the need for marriage. That’s a part of our job. We make sure we are matching members that are compatible. Our advice is to take your time and let the relationship evolve. Don’t push it. If it’s meant to be it will blossom like a flower.

Ron Cater


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