CT matchmakers
Lory Kelsey and Jill Dunn aim to help locals find love in the digital dating era
In a society ever lenient on social media and app-based dating services, some Nutmeggers are turning to the old-school traditions of matchmaking for their next shot at love.
Connecticut singles can opt out of signing up for sites like Tinder or Bumble and hire someone like Greenwich’s Lory Kelsey or Norwalk’s Jill Dunn
— two women who turned their own searches for love into finding love for others.
Dunn owns the matchmaking service
Jillin’ It. Becoming a matchmaker was a way for her to “bring people together,” she said. After getting divorced in 2016, it was hard for her to find any events for singles to meet or connect living in Norwalk.
“I started my business in 2018 by throwing singles mixer events for people to meet,” Dunn said. “I had a background in throwing events, so as a person who loves love, I wanted to connect the two.”
Dunn would meet people at the events and keep people in the back of her mind as potential matches.
“Once I find someone I think they’ll like, I reach out to them. If it’s a match for both parties, I coordinate a time and a place for them to meet,” Dunn said. “After every date, I check in with clients and see what went right and what went wrong. This helps guide their next date.”
Kelsey owns Greenwich Matchmaker. She also got into matchmaking after a divorce.
“I live in Greenwich and was looking to date in Greenwich and thought to myself, ‘Maybe I should be the Greenwich matchmaker,’ ” she said. “For a year and a half, I interviewed women and added them to my database.”
Both women said their backgrounds in other fields help them in matchmaking. Kelsey studied social work and Dunn has a background in teaching.
“I was born to teach and I make sure to make this experience as comfortable and teachable for my clients [as possible],” Dunn said. “Dating should be fun and enjoyable. It should not feel like a chore.”
To Dunn, success in dating does not mean finding your end point. It’s about the process and helping clients learn from each experience, even if that’s learning about what they definitely do not want in a partner, she said. Her own experiences in dating help her help others, taking the lessons she has learned from her own dating trials and using them to get her clients in the right head space to be open to dating and finding love.
The matchmaking process starts with clients filling out a form with questions about their age and location as well as romantic “deal breakers.” The matchmaker then schedules a call to get a better understanding of who the client is and who their “ideal partner” might be. Then, they check if the person is suitable for matchmaking and, eventually, try to find a match. Kelsey said getting drinks or coffee is a great first-date idea. It allows a couple to linger or leave depending on the chemistry. Kelsey said compatibility can still lead to confusion. She was once contacted separately by a husband and wife going through a divorce. Neither knew the other was using a matchmaker, then found out they’d been using the same one. “I had been working with both of them a little while when I was contemplating setting the two of them up for a date since they seemed to be a match,” Kelsey said. “Luckily the three of us were spared the embarrassment because the divorced husband had just revealed to his wife that he was working with a matchmaker as well.”
Kelsey knows of people who create stories to avoid the stigma surrounding meeting through a paid service. She hopes the stigma will fade with dating apps becoming the norm. She also believes matchmakers can help clients dig deeper to find better matches when using apps. “I am not opposed to my clients using dating apps — in fact, we help with their profile,” Kelsey said. “But one thing I do enjoy about matchmaking is really getting to know my clients in an emotional way rather than what they see on a screen.” Dunn said services extend beyond simply setting people on dates. She said coaching and courses are among the most important services she offers. “You have to know what you look for in a relationship — red flags, deal-breakers and more about yourself to really know what you are looking for.” Dunn said. “Nothing is better than learning about yourself and knowing your worth.”