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

  • Writer: Jill Dunn
    Jill Dunn
  • Apr 1
  • 4 min read
Singles Sparks, Your Weekly Love Link, Jillin It. Professional, Local, CT matchmaker, Jill Dunn

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 investmentshouldn’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!

Woman joyfully holding blue and green balloons against a cityscape. Text: "Single Again in the City, April 14th, 7:10 PM, 96.5 TIC."

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...


Get your ticket here.


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.

Woman in red cap smiles while on phone. Text: The Love Line with Jill. Caption: I DID NOT SEE THAT COMING. Black hoodie, mic visible.

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.

Read about it here and tell me what you think!

A woman plays guitar and sings in a subway with flyers on the wall. Subtitles read, "Your love is like a giant pigeon, crapping on my heart."

TOP 3: Patterns that Someone is Seeing Other People

  1. Their availability feels selective: If they’re consistently hard to pin down on evenings or weekends, tend to make last-minute plans instead of scheduling ahead, or go quiet during predictable times, it can suggest they’re fitting you in around other priorities rather than building something with you.

  2. Their words and actions don’t match: They might express strong interest, but their actions don’t consistently back it up. You may notice affection when you’re together followed by distance afterward, or vague, non-committal answers when you talk about what they’re looking for.

  3. The connection doesn’t deepen over time: When someone is dating multiple people, their attention is divided, and the relationship can feel like it’s stuck in place. Conversations may stay surface-level, they might not show much curiosity about your life, and there’s no real planning ahead or integration into each other’s worlds.


Book a call with me to see if I can help you meet your dating goals. Email me

Woman sitting in a room with purple walls, wearing a gray top and watch, looking surprised with hand on chin; framed picture in background.

CT and NY Matchmaker Insights for Singles

The Funnies! Because You’ve Got to Laugh…

Man sitting outside in a garden setting with a pool, wearing a black shirt. Text above: "when I ask myself why I'm single." Subtitled: "You know, I've realized that I'm probably just perfect and it's everybody else around me that's got issues."

A woman at a reception desk looks unimpressed. Top text: "When my married friends keep insisting on setting me up." Bottom text: "Please don't throw garbage at me."











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!


CT and NY Matchmaker Insights for Singles Jill Dunn Jillin' It



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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