Singles Sparks - CT and NY Matchmaker Insights for Singles - May 3 Edition

Hello LoVers,

In the last 30 days, we’ve coordinated a record-breaking number of dates, sending over 60 carefully selected singles out on first introductions. It has been a full, fast-paced time, and I have to say… it truly fills my heart. Even more meaningful many of those have already unfolded into second and third dates, which is where real potential for connection begins to take shape.

It’s also been an exciting and active time for the Jillin’ It team! I was recently featured in Maxim, highlighting the work we’re doing behind the scenes to curate exceptional matches for relationship-ready individuals, alongside some incredible colleagues in the industry.

This week, I’ll be in NYC for three days attending the Global Love Institute conference, joining over 150 dating professionals from around the world. It’s one of the most energizing and fulfilling weeks of my year, not only because I’m constantly learning and evolving, but because of the level of collaboration that happens in these rooms. Sharing my clients with trusted colleagues and learning about theirs opens the door to an entirely new level of opportunity. Some of the most aligned, high-quality matches come from these conversations and I’m excited about what’s ahead.

If there’s one perspective I want you to carry into your dating life this week, it’s this:

The first date is not the decision point, it’s the discovery point.

So many high-caliber individuals approach dating like an evaluation process, looking for certainty too quickly. But the strongest, most lasting connections are often built not instantly recognized.

Allow for a second date. Let curiosity lead before judgment does. The right connection deserves a moment to reveal itself. If dating has started to feel transactional, frustrating, or like it’s not leading where you want it to, that’s often where a more intentional, guided approach can make all the difference.

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 seagulling. Plus, read our TOP 3 reasons people send mixed signals. 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 serviceis right for you.

Big love to you always!

xo,

Jill

Incase you missed it…

She has a crush on her co-worker's HUSBAND! Here's my advice:

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.

As Featured in Maxim!

Finding love in 2026 looks nothing like it did a decade ago. Between AI-curated dating apps, a post-pandemic reset of relationship expectations, and a growing demand for real human connection over algorithmic swipes, more singles than ever are turning to professional matchmakers and relationship coaches to navigate it all.

I'm honored to have been featured alongside such respected peers who are reshaping modern dating. 

Click here to read all about it. 

Singles Spotlight: Is SHE Your Match?

MEN, ages 49 and under, who are interested in a child-free lifestyle in the NYC area… does this sound like you? Are you confident, kind, attentive, and playful? Are you successful and financially stable? Do you enjoy good food, great trips, and spontaneity?

If this sounds like you, you may be a match for my warm and charming client, K. K is emotionally self-aware, an excellent listener, and empathetic. She has an engaging personality, strong personal integrity, and values honesty. She is an avid reader who enjoys exploring the city, discovering great restaurants, and walks in the park.

If you are a good match and are interested in learning more, email me!

HOT TOPIC: What is Seagulling?

As with many of these terms that appear on social media or the rest of the Internet, it's not clear who specifically originated the "seagulling" term. But it is clearer why people have been giving this dating practice the bird, so to speak. It's similar to the tendency of seagulls to grab food whether or not they are hungry simply because they don't want others to get the food.

Read about it here and tell me what you think!

TOP 3: Reasons People Send Mixed Signals

1. They Don’t Trust You. Not everyone gives new partners the benefit of the doubt. Whether they're being prudent or whether they’re hesitant to trust you because they’ve been burned in the past is something you’ll have to find out as you get to know them.

2. They Fear Commitment. Exclusive involvement with another person doesn't appeal to everyone. Some people highly value their independence and freedom. Some have avoidant attachment styles that incline them to interpret closeness as threatening.

3. They Want to Feel in Control. This may come from a deep fear of abandonment or mistrust. Or from a more nefarious personality style. Keeping you in a constant state of guessing and lack of certainty could be a way for someone you're seeing to feel like they’re holding the reins.

   
   

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

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.