Meet Lory Kelsey [Best Connecticut Matchmaker For You?]

Lory Kelsey is a Greenwich-based matchmaker who founded Greenwich Matchmaker LLC in 2012 after struggling to find matchmaking services in her own community. With a Master's in social work and Bachelor's in psychology, she serves singles within 100 miles of Greenwich, including throughout Connecticut and New York. Consultations cost $600/hour (1–2 hours typical); package pricing is customized per client. She specializes in "higher net worth individuals" aged 25–60 and limits her client roster for personalized attention.

Key Insights:

• Lory Kelsey founded Greenwich Matchmaker LLC in 2012 after discovering no local matchmakers served her area
• She holds a Master's degree in social work and Bachelor's in psychology
• She primarily works with singles within 100 miles of Greenwich, serving Connecticut and New York
• Professional consultations cost $600/hour (typically 1–2 hours); matchmaking package pricing is customized
• Database registration costs $600 for a 1-hour interview with profile active for 5 years
• She prefers working with "higher net worth individuals" aged 25–60 for female clients
• Kelsey also offers dating coaching and life coaching internationally via video call

Our team of experts has reviewed 200+ matchmakers, from boutique agencies and celebrity matchmakers to the big international services. 

Our reviews are based on extensive research, 15+ years of matchmaking experience, client reviews, and more. We’re intimately familiar with what clients value most in a service, so let’s dive in!

Lory Kelsey is the founder of Greenwich Matchmaker LLC, a boutique matchmaking service she launched in 2012.

Her path to matchmaking began from personal experience. As a single parent following her divorce, Kelsey struggled to meet someone special in Greenwich. She searched the internet repeatedly for "Greenwich matchmakers" but came up empty-handed.

She recounted her experience in an interview with Hamlet Hub:  

“There didn't seem to be any matchmaker nearby in my immediate area. So it began occurring to me that I could and should fill the role for my extended group of single friends that found themselves single in the same situation year after year.” 

Kelsey's professional background included working as a representative for a dating service called Turning Point International. Reflecting on her experience, Kelsey felt she "had been quite successful at it."

As she began to realize the demand for matchmaking within her own community, Kelsey felt something was calling her to become the matchmaker she had been searching for.

In her own words, 

“It’s very difficult at times to meet someone you’d like to meet in Greenwich… Finally, I’m like, ‘I think someone’s telling me I need to be [the] Greenwich Matchmaker’.”

In 2012, she opened Greenwich Matchmaker LLC, catering to clients throughout Connecticut and New York.

With a Bachelor's degree in psychology and a Master's degree in social work, it’s no surprise Kelsey often dispenses dating and relationship advice to her clients. 

She has also shared dating tips through social media and in interviews with various media outlets. Here are 4 of her best dating tips for Greenwich singles!

Kelsey is a boutique matchmaker who limits the number of paying clients she works with at any given time. As she explains, she's selective—it's not for everybody.

As a paying client you can expect to work closely with Kelsey. She emphasizes the importance of building deep relationships with her clients on an emotional level.

“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.” 

Who She Works With

Kelsey primarily serves singles within 100 miles of Greenwich, though she takes on clients throughout Connecticut and surrounding areas in some instances.

For her "Private Lady Clients," she prefers working with "higher net worth individuals" aged 25–60.

Both men and women can purchase matchmaking packages or join her registry of eligible singles.

Additional Services

Kelsey also offers dating coaching and life coaching services internationally, with appointments conducted via Zoom, Skype, phone, or other platforms.

If you're interested in working with Kelsey, you'll fill out an application on her website. If you pass initial screening, she'll schedule a short, complimentary call. If both parties want to proceed, you'll schedule a "Professional Consultation."

Professional Consultation

The consultation costs $600 per hour and generally lasts 1–2 hours. During this meeting, Kelsey gets to know you in depth.

Matchmaking Process

If you move forward and sign a contract, you'll be matched with compatible singles from her database or from her network.

As a paying client, both men and women are guaranteed introductions. For an additional fee, first date details will be arranged for you.

After each first date, Kelsey checks in with both parties and passes along feedback.

Database Option

You can also join her singles registry without purchasing a matchmaking package. This requires a 1-hour interview costing $600, with your profile active for 5 years.

However, this is a passive option—no matchmaking is done on your behalf. You'll only be contacted if you happen to match what a paying client is seeking.

Database Registration: $600 (1-hour interview; profile active for 5 years)

Professional Consultation: $600/hour (typically 1–2 hours)

Matchmaking Packages: Pricing isn't listed online. Options are tailored for each client based on their situation and needs.

Additional fees apply for having first date details arranged.

Lory Kelsey brings academic credentials (Master's in social work, Bachelor's in psychology) and personal experience as a divorced single parent to her matchmaking practice. Her boutique approach—limiting clients for personalized attention—appeals to those seeking a hands-on, emotionally connected experience.

The service works best for higher-net-worth singles in Connecticut and New York (within 100 miles of Greenwich), those who value deep, emotionally focused matchmaker relationships, clients comfortable with $600/hour consultation fees plus customized package pricing, and singles open to Kelsey's "keep an open mind" philosophy about criteria.

For the full picture including client experiences, check out our Greenwich Matchmaker review.

For singles seeking transparent pricing and month-to-month flexibility, VIDA Select offers matchmaking starting at $1,595 with no long-term contracts. VIDA's matchmakers leverage the largest pool of Connecticut and New York singles available, and you pre-approve every match based on full profiles with photos. Most clients meet someone special within 3 months.

Ready to explore your options? Schedule a free, confidential consultation to see which approach fits your goals.