Singles Sparks - CT and NY Matchmaker Insights for Singles - May 17 Edition
- Jill Dunn

- May 18
- 4 min read

Hello LoVers, If you walk into the grocery store without a list, without a recipe in mind, and without any real plan… you’ll probably wander the aisles tossing random things into your cart based on what looks good in the moment. Before you know it, you’ve spent $400, get home, and somehow still don’t actually have the ingredients to make a real meal. Dating can work the exact same way. Now to be clear... I am NOT a fan of rigid checklists or eliminating someone because they’re two inches shorter than your “type,” three years older than your preferred age range, or don’t love the exact same hobbies as you. NO, no, NO! But I AM a huge believer in understanding the core ingredients that actually matter for the kind of relationship and life you want to build with a partner. Compatibility is usually less about surface-level preferences… and more about ALIGNMENT. Things like:
I actually talked about this on last week’s Love Lineon the radio... Finding the right partner is often less about AGEand more about life STAGE. I’ve seen couples with 10+ year age gaps who make complete sense together because their lifestyles, maturity, energy, and relationship and family plan goals ALIGN beautifully… and I’ve seen people the exact same age who are completely incompatible. The goal isn’t to find someone who checks every random box. The goal is to find someone whose life flows naturally with yours. That’s YOUR RECIPE. Dating based on CHEMISTRY alone, ATTRACTION alone, or “POTENTIAL” alone… then wondering why they keep ending up with a cart full of ingredients that don’t actually work together long term. So, let this be your reminder. Get clear on the ingredients that truly matter to you. Not the ones social media told you to care about. Not the ones your friends prioritize. YOURS. And if you want someone to help you sort through what actually matters versus what’s just noise… we do that. This is literally what I love helping people untangle. If you’re ready to approach dating with intention, discernment, and a process that is both thoughtful and highly personalized... I am here for you. Not quite ready for full-service matchmaking? Join the Jillin’ It SIngles Network to be considered for current and future clients. You never know… Want to chat? Get in touch to schedule a complimentary 15 minute call to see if my private and personalized Matchmaking service is a fit for you. In this week’s HOT TOPIC, we’re talking about situationships. Plus, read our TOP 3 reasons you lose interest so fast. And don’t miss this week’s funnies at the bottom. Gotta laugh because this dating game is NO JOKE! Check this week’s Singles Spotlight to see if YOUR match is featured this week. Then, click here to schedule a 15 minute call so I can learn a bit more about you and see if my private and personalized Matchmaking service is right for you. Big love to you always! xo, Jill |
Incase you missed it… |
Stop asking, “What are we?” … and start asking, “What actually works for me? |
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Did you know that I’m answering your dating questions on the radio every Thursday at 7:30 am on The Christine & Salt Show on 96.5 TIC? Have a question you want answered on air? Submit it here. |
Singles Spotlight: Is SHE Your Match? |
MEN, ages 69-78... does this sound like you? Are you grounded, emotionally intelligent, curious, and genuinely kind? Do you have a great sense of humor and enjoy meaningful conversation? Do you feel comfortable in creative and culturally engaged spaces? If this sounds like you, you may be a match for my engaging and warm client, J. J has built a vibrant, intentional life centered around art, culture, travel, and meaningful relationships. She’s thoughtful, creative, loyal, and quietly witty, with a satirical sense of humor and a natural ability to make people feel at ease. Whether she’s hosting dinners in the Hudson Valley, traveling through Europe, attending theater performances, or spending time with close friends and family, she brings warmth and curiosity to everything she does. If you are a good match and are interested in learning more, email me! |
HOT TOPIC: The Truth About Situationships |
For years, ambiguity has shaped modern dating. Situationships, unlabeled relationships without clear direction, often show up in the space between dating apps, casual texting, and the familiar "we're just seeing where it goes" conversation. They're often framed as freedom: No pressure, no expectations, and plenty of room for things to unfold naturally. For many people, however, that freedom doesn't feel like ease. It feels like uncertainty that never fully shuts off. |
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TOP 3: Reasons You Lose Interest So Fast |
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CT and NY Matchmaker Insights for Singles
The Funnies! Because You’ve Got to Laugh…


CT and NY Matchmaker Insights for Single
CT and NY Matchmaker Insights for Singl
Curious about Matchmaking? Schedule a call to see if my matchmaking service is something we should consider for you.
I’m here for you with more opportunities than EVER! Year round singles events, The Match of the Month Blind Date Activation, Jillin' It Singles Supper Club, Solo to Sparks Dating Intensive, my private and personalized Matchmaking service, complimentary singles network and 203 Singles Facebook group, Meet Up Group, The Four Day Flip and so much more. Here for you!

Curious about Matchmaking ? Schedule a call to see if my matchmaking service is something we should consider for you.l to see if my matchmaking service is something we should consider for you.all to see if my matchmaking service is something we should consider for you.
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