Ask a Matchmaker
adulting
Fewer swipes to more sparks—how to find love in Maine
words by jill hinckley & lynda adams
interview by maggie knowles
We asked two professional matchmakers, Jill Hinckley of Hinckley Introductions and Lynda Adams of Cara Matchmaking, to share their thoughts on finding authentic love connections outside of the apps–especially during the long months of Maine’s winter and spring.
Meet The Matchmakers:
Jill Hinckley is a professional matchmaker and founder of Hinckley Introductions, a boutique agency with locations in Maine, Massachusetts, and Florida. Known for her warm, intuitive approach, she helps singles—especially those over 40—build meaningful connections. A Southwest Harbor native, she brings deep roots and genuine heart to every match.
Lynda Adams is a professional matchmaker, certified relationship coach, and owner of Cara Matchmaking, based in Falmouth. Married for 23 years, she brings experience, insight, and a natural ability to connect people to create a safe, joyful, and intentional space where singles feel seen, supported, and ready for real connection.
What’s the biggest dating misconception people have about meeting someone in Maine?
Jill: We call these limiting beliefs. People often come to me and have several limiting beliefs about meeting potential connections that hold them back. I like to turn these thoughts around with successful examples from my years in the business. I meet with Mainers every week, and they are all open to new connections.
Lynda: Many people come to me feeling discouraged, believing the “good ones” are already taken. In reality, there are thoughtful, relationship-ready people everywhere—they’re often busy living full lives and staying connected to their communities, not limiting love by location.
The issue isn’t availability—it’s how and where people are connecting.
To those who think their “one and only” is going to pop through their phone as they scroll the apps from the couch, what do you say?
Jill: It’s possible, but why would you throw all of your eggs in one basket? There are countless ways to meet your “one and only.” Take time to do a little research and find the dating platforms that will work for you. Also, one of the best ways to meet your person is to simply be more involved in your community. Think about joining a nonprofit organization or start a co-ed book club. You’ll be amazed at how many people you will meet.
Lynda: There are many great people on dating apps, but filters and must-haves can cause meaningful connections to be overlooked. Real chemistry can’t be screened. A woman in her 60s attended one of my singles events and afterward followed her love of music to a local spot with live bands. That evening, she unexpectedly met a man, and they fell deeply in love. It’s a beautiful reminder that connection often shows up when we’re open to change and doing what brings us joy.
Do you have a favorite “first date” idea that allows one to see many aspects of a potential partner’s personality?
Jill: A first date needs to be in a location where you can talk without a lot of distractions. It’s also important to have a conversation that is fun, upbeat and focuses on the present and future! I love it when people come prepared with interesting conversation starters like … what is your favorite time of the year or what do you like to do on a rainy day in Maine?
Lynda: I love a first date that allows for easy conversation and flexibility, like a walk with coffee where you can stop and sit on a park bench, or meeting at a restaurant bar. These settings naturally create closeness and reveal how someone communicates and engages with others. The goal isn’t to impress—it’s to see how it feels to be yourself together.
From your experience, what small gestures make a big impact on a first date?
Jill: This is an easy one. Smile! It only takes seven seconds to make a first impression, so when a person smiles it sets the tone for the rest of the date!
Lynda: The small gestures that matter most show presence and intention—eye contact, genuine listening, and kindness go a long way. Remembering something they shared before the date and referencing it later lets someone know they were truly heard, and a warm hug or thoughtful mention of seeing each other again can shift the energy from polite to romantic. People remember how you made them feel more than anything you said.
What’s the most surprising lesson you’ve learned from your careers in matchmaking?
Jill: I’ve learned that love is simple and not as complicated as we sometimes think. We tend to get hung up on things that are not important for the success of a long term relationship. We only need four things for a relationship to be successful—Trust, friendship, intimacy and support. Everything else is a bonus!
Lynda: One of the most surprising lessons I’ve learned is how fear of rejection influences dating, even for confident, successful people. It can cause them to become rigid about who they think they’re looking for. When clients soften expectations, focus on shared values, and allow clarity and reassurance to build, real connection has room to grow. Often the shift comes when they realize it’s not just about finding the right person, but becoming the kind of person who naturally attracts the relationship they want.
How can singles who are happy on their own respond to family or friends who keep asking when they’re going to meet someone?
Jill: They need to set up boundaries with their friends and family members. Just let them know that you are happy with your life and will let them know if you need their advice. It can be hard to set these boundaries, but it is worth it!
Lynda: It helps to remember that questions from family and friends often come from a place of love. Singles who are genuinely happy tend to show it through how they live, not through explanations, and a calm response like, “I’m open if love comes into my life, and I’m also really enjoying where I am right now,” sets a confident, grounded tone. When fulfillment is visible, others naturally trust your path and tend to ask less often.
If you could give one tip for keeping the spark alive through Maine winters–even to existing couples- what would it be?
Jill: Say, “I love you!” Make plans to do something together even if it’s just going to the grocery store together. We all tend to hibernate in the winter and can put our relationships on the back burner, but be proactive with your love life–little actions go the distance.
Lynda: Maine winters can be a powerful time to deepen connection when couples are intentional. With fewer distractions, simple rituals like at-home date nights, cooking together, music, and candlelight help keep romance and playfulness alive. When love is actively nurtured, winter becomes a season to enjoy, not just get through. Follow these tips and you will find yourself on every guest list throughout the season.
