Best Maine Matchmakers [Top 6 Dating Services Compared!]

Maine's top 6 matchmakers range from $499/year (Cara Matchmaking) and $400-$2,000+ (Matchmaker of Maine) to $20,000+ for 6 months (Enamour), with VIDA Select offering month-to-month flexibility at $1,595+ and Elegant Introductions, Hinckley Introductions, and Smart Funny Single providing boutique services with customized pricing.

💡 Key Insights:

• Wide pricing spectrum: Maine matchmakers range from $499/year (Cara Matchmaking with unlimited introductions) to $20,000+ for 6 months (Enamour), with mid-range options at $400-$2,000+ (Matchmaker of Maine), several thousand (Hinckley Introductions, Smart Funny Single), and flexible monthly service starting at $1,595 (VIDA Select)
• Only month-to-month option: VIDA Select offers month-to-month packages with no long-term contracts, while most others require 6-12 month commitments with typical contracts lasting one year
• Niche specializations: Services specialize in different demographics—Elegant Introductions for New England natives valuing authenticity, Hinckley for boating enthusiasts 40+, Matchmaker of Maine for 40+ singles, Smart Funny Single for 50+ dating, Cara for those dating in their 40s-50s
• Traditional vs modern approaches: Cara uses paper files and sticky notes ("old school"), Matchmaker of Maine offers traditional database matching since 1997, while VIDA provides modern unlimited access with 82% success rate and clients meeting someone within 3 months
• Boutique client limits: Hinckley Introductions limits active clients to around 20 per year for personalized attention, reflecting boutique model common among Maine matchmakers versus VIDA's scalable approach
• Free database options: Multiple services offer free database inclusion (VIDA, Cara, Hinckley, Matchmaker of Maine) with no guaranteed matches—only contacted when fitting paying clients' criteria
• Complementary services included: Many offer styling, coaching, and photography—Enamour provides personal styling/relationship coaching/image consulting/photography, Elegant Introductions includes coaching/styling/photography/confidence building, VIDA offers styling/consulting/coaching

You’ve likely realized that when it comes to hiring a Maine matchmaker, you’ve got more than a few options to choose from, especially in places like Portland, with its vibrant, urban feel, and Cape Elizabeth, known for its charming coastal beauty.

Whether you're navigating the dating scene in a bustling city or a quieter seaside town, deciding which one is the best choice for you can be tricky. 

From cost to experience to the process they use, every service puts their own spin on finding your ideal partner. And that’s exactly where this list of the 6 top Maine matchmaking services is going to come in handy!

Let's get started with...

Enamour's matchmaking team has been helping singles throughout New England and beyond meet high-quality matches since 2009. Known for its white glove, highly tailored approach, Enamour's matchmaking process incorporates relationship psychology, personality profiling, and intuition.

Clientele

Enamour works with accomplished, selective singles looking to meet incredible matches.

Cost

Matchmaking packages begin around $20,000 for a 6-month search.

What To Expect

After being paired with your dedicated personal matchmaker, she'll get to know all about you, your lifestyle, and your matching preferences and criteria. Then, the search begins within Enamour's curated, invitation-only database.

The matchmaking team also uses recruiting tech as well as a network of scouts to pinpoint candidates both online and offline. Each one is vetted via a thorough, in-person or video screening process. Those who pass will be presented to you for approval.

Following each date, you'll have the opportunity to provide feedback, and your matchmaker will be in touch with your match as well. She'll pass along any helpful insights, and will use your feedback to fine-tune the search as needed.

Enamour also offers a range of services to complement the matchmaking process, including personal styling, relationship and dating coaching, image consulting, and professional photography.

Wherever you’re in Portland, Bangor, Lewiston or anywhere else, if you’re dating in Maine VIDA Select can help! 

Founded in 2009, VIDA's team has access to the largest dating pool in Maine. It’s no wonder the typical VIDA client meets someone special within the first 3 months of service!

Clientele

Typically, clients are successful, career-minded professionals in their early 30s to mid 60s.

Cost

Monthly matchmaking packages start at $1,595, with no long-term membership contracts required. Clients can also opt for the "90-Day Match Guarantee" package, which includes at least 5 highly curated matches you personally approve for $5,750.

With an 82% success rate, clients typically meet someone special within 3 months of starting service.

What To Expect

The first step in VIDA’s matchmaking process is a quick screening process to make sure you’re a good fit for the service. 

That’s followed up with a complimentary phone consultation where you’ll learn how it works, and you can share your relationship goals, matching criteria, and other details. 

Then you’ll have an in-depth call with your matchmaker where she’ll get to know all about you and what type of matches you hope to meet.

Once she’s got a good idea of your ideal partner criteria, VIDA’s team gets to work hand-selecting highly compatible matches for you to approve!

VIDA also offers all the resources you need to make a great first impression, like personal styling, image consulting, and dating coaching.

At Elegant Introductions, they believe the most important relationships begin with authenticity, respect, and a personal touch - qualities often missing from today’s fast-paced dating world.

The service was founded by Dr. Nancy Zimmer and Barbara Black Goldfarb, both proud New England natives. Having grown up in this region, they live by the New England values of integrity, sincerity, honesty, thoughtfulness, and a belief that the right relationship can truly transform your life.

The duo understands the heartbeat of Maine - the independent spirit, the warmth of real connection, and the genuine pride in living authentically. So whether you live in Portland, along the coast, or in one of Maine’s charming towns, they can help you find a partner who matches not just your lifestyle, but your heart.

Clientele

Elegant Introductions works with successful, accomplished Maine singles—leaders, innovators, entrepreneurs, creatives, and professionals—who are serious about finding meaningful relationships.

Clients are often ready to leave behind dating apps, endless scrolling, and surface-level encounters and meet matches curated with thought, heart, and real compatibility in mind.

Cost

Pricing for services is customized based on the scope of the search, your preferences, and geographic reach. Packages are tailored to the needs and timeline of each client.  

What To Expect

The Elegant Introductions process is personalized and intentional, designed for discerning individuals who are serious about finding a relationship. It all begins with a private, confidential intake form, where you'll share in-depth details about your life, core values, past relationships, and your vision for the future.

Once your intake form is reviewed, you'll be invited to a discovery call, where you’ll have a one-on-one conversation to learn all about the Elegant Introductions' matchmaking approach. It's also an opportunity to get to know you on a more personal level and answer any questions you may have about the selection process and philosophy.

If both parties agree, the next step is scheduling a consultation with Dr. Nancy Gold-Zimmer and Barbara Black Goldfarb. This is an insightful discussion about your relationship journey, the lessons you've learned, how you've grown, and the kind of partnership you're looking to build. 

Clients can expect a completely custom search strategy, with every introduction hand-picked and arranged for you.

Elegant Introductions also includes additional resources with the service:

• Private relationship & dating coaching
• Personal styling consultations & image enhancements
• Professional photography
• Confidence building & communication coaching

For more information, check out our Elegant Introduction Reviews! 

Ron Cater has been in the matchmaking industry since the early 80s, although his original career choice was dentistry. As he explained to The Portland Phoenix, he was in dental school when a conversation with a friend in the matchmaking industry sparked a career change. 

He started talking to me about this whole industry and what they did and how they worked and I didn’t even know it existed. It was just very, very fascinating.

Cater also owns another New England matchmaking service called Successful Singles, based in Boston. The Matchmaker Of Maine was founded in 1997, with its headquarters in Portland. Cater has locations in Massachusetts and New Hampshire as well.

Clientele

While memberships are open to singles of all ages, Cater typically works with men and women in their 40s+. Despite the name, this dating agency takes on singles all over New England.

Cost

The Matchmaker Of Maine doesn’t advertise prices online, but clients reported spending anywhere from $400 for a 3-month membership to $2,000+ for a longer one. 

What To Expect

The first step in the membership process is a 40-minute free consultation where you’ll introduce yourself and talk about the type of people you’d like to meet through the service. Prospective clients can book the consultation online or fill out a contact form.

As Cater told DatingAdvice.com, they don’t take on just anyone who inquires. Would-be clients must be “emotionally ready, emotionally available, and have realistic expectations of what they’re looking for.”

After the screening process, clients take a series of personality and compatibility quizzes to help the matchmakers narrow down potential candidates to meet. Cater and his team take a traditional approach, in that you’ll be introduced to other members in The Maine Matchmaker’s database.

For more information, check out this Matchmaker of Maine review!

Maine matchmaker Noreen Rochester is based in Biddeford, just outside of Portland. Rochester says her business is “old school.” As she explained in an interview with Portland Phoenix,  

I don’t have a database, I have pink and blue and yellow files and a million sticky notes.

She’s been matchmaking for over 30 years in some capacity, and launched her Maine dating service in 2013. Cara Matchmaking gets its name from the Gaelic word for “beloved companion.”

Clientele

Rochester primarily takes on singles in their 40s and 50s, although she told The Portland Phoenix that recently she’s been helping people in their 30s and even 20s as well.

Cost

$499 for one year of services.

What To Expect 

The process starts with a complimentary initial consultation. You’ll discuss what you’re looking for in a relationship, your partner preferences, etc. 

If you decide to sign up, you’ll meet other Cara Matchmaking clients who meet your preferences (and vice versa) over the course of your year’s membership.

Potential matches get to see each other’s photos, and whenever there is mutual interest Rochester arranges the date or or phone call.

Memberships include unlimited introductions as well as invitations to member’s only events.

Curious about Rochester's dating service? Check out our Cara Matchmaking review!

A fixture in Maine’s boating scene, Jill Hinckley’s grandfather founded Hinckley Yachts back in 1928 and Jill Hinckley grew up in the family business. When it sold in 1998, she became a managing partner of a search and recruitment firm for the marine industry.

Using that experience, Hinckley branched out into matchmaking in 2013. As she explained during an interview with News Center Maine,  

When I was doing the recruiting and I was meeting the people that were looking for jobs in the boating business, I connected with their personal story. I also had all these single friends that said, 'Jeez Jill, we need someone to help us find people.'

Her boutique dating agency, Hinckley Introductions, is based in Portland and has a branch in Chestnut Hill, MA.

Hinckley also founded Make Your Match, a closed Facebook community of affiliated matchmakers and dating coaches who help singles ages 35 and up.  

Clientele

Most of Hinckley’s clients are singles over 40, and she takes on both men and women as paying clients. Given her love for boats and the ocean, she has “found a niche” with similarly minded clients. 

Much of her database contains Maine singles, but she works with clients looking to date in other states as well.

Cost

Potential clients can start with a free 20-minute phone call to learn more about the service. You can join the Hinckley Introductions database for free and wait to be matched with paying clients, or you can take the next step in the matchmaking process. 

That’s a 60-minute consultation with Hinckley to discuss how her matchmaking program works, which costs $120. 

This Maine matchmaker doesn’t advertise her prices online, but does refer to the service as “in investment” on her website. You can probably expect to spend at least several thousand on a membership. Contracts typically last 6 to 12 months.

What To Expect

As with most boutique matchmakers, Hinckley limits the number of “active” clients she has at any given time to around 20 each year.

Once you’ve purchased a membership, filling out an extensive questionnaire is the next step. It covers everything from your background and lifestyle to your occupation, interests and political views. 

Hinckley then uses those details to pair you with other singles in her database, or she’ll reach out to matchmakers within her network for potential candidates. As she told Old Port magazine, 

I love working with other matchmakers. If another matchmaker in Boston, for example, has a client they’re working with, they might contact me and see if anybody in my database or anybody I’m working with might match up with their client.

Once a suitable match has been identified, she puts both people in contact with each other.

Hinckley also offers dating coaching. To learn more about this Maine matchmaking service, check out our Hinckley Introductions review!