Singles Sparks - CT and NY Matchmaker Insights for Singles - March 29 Edition
- Jill Dunn

- Apr 1
- 4 min read

Hello LoVers, You won’t believe the question I answered on the Love Line this week. Let’s just say if dating has started to feel a little… transactional lately, you’re not alone. Rachel from Avon, CT shared that she went on a date, had a nice time, but didn’t feel a romantic connection. She let him know kindly in a text message the next day. His response? A thumbs up… followed by an Apple Pay request for half the bill. AH!!! Funny? Yes. Kinda… But also a really good reminder of something deeper. When you go on a date, the “return on investment” shouldn’t be anything more than the opportunity for human connection. Not a guaranteed second date. Not chemistry. Not a relationship. Just the chance to meet another person, share a moment, and see what unfolds. The moment we attach expectations, emotional, romantic, or even financial, we set ourselves up to feel shortchanged. Dating requires a level of generosity. Of spirit, of time, of energy. And yes, sometimes that generosity is met with something meaningful… and sometimes it’s just a pleasant evening and a story to tell. Both count. Both are part of the process. The right connection isn’t something you extract, it’s something that reveals itself over time. And if dating has started to feel transactional, frustrating, or just not leading where you want it to, that’s often where a more intentional, guided approach can make all the difference. 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 10 minute call to see if my private and personalized Matchmaking service is a fit for you. We have a fun event coming up in collaboration with the Hartford Yard Goats Baseball team! Check it out + in this week’s HOT TOPIC, we’re talking about the micro-breakup. Plus, read our TOP 3 patterns that someone is seeing other people. 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 10 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 |
Join us for Single Again in the City on April 14! |
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Join us, in collaboration with Christine & Salt from the 96.5 WTIC Morning Show, forSingle Again In The City - a downtown Hartford divorce party with music, cocktails, and serious glow-up energy. Put on your best outfit, gather your friends, and come make a toast to the future! This ticket secures your seat to the game, and also gives you entry to the Singles Mixer in the Patron Party Porch, hosted by yours truly. Casual fun with low key icebreakers to help singles make connections. Wingman welcome! You never know who you'll meet... |
Incase you Missed it on the Radio… An Apple Pay Request? |
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. |
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Singles Spotlight: Is SHE Your Match? |
MEN, ages 60-75… Does this sound like you? We are looking for a golfer who has the freedom and flexibility to travel between Connecticut and Florida (and beyond)! Are you spontaneous, extroverted, and passionate? Do you have a good sense of humor and an appreciation for the simple things in life? If this sounds like you, you may be a match for my thoughtful and genuine client, N. N is down-to-earth, loyal, and values calm, meaningful connections. She leads an active lifestyle, enjoying golf, yoga, and spinning for both health and relaxation. Naturally introverted, she thrives in one-on-one settings where her wit and intelligence shine. If you are a good match and are interested in learning more, email me! |
HOT TOPIC: The Rise of the Micro-Breakup |
You weren’t together, together. But you still talked every day. You shared playlists. Obsessed over shows. Had secret recipes. They came to your grandmother’s funeral with her favorite flower. You knew their childhood dog’s name and their attachment style. You are each other’s person, but then gradually texts became more sporadic and eventually disappeared. Technically, nothing ended, since it wasn’t a “thing.” But you feel devastated and grief-stricken. |
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TOP 3: Patterns that Someone is Seeing Other People |
Book a call with me to see if I can help you meet your dating goals. Email me |
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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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