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Singles Sparks - CT and NY Matchmaker Insights for Singles - February 1 Edition
What women want on a date and what men want on a date aren’t always the same and that makes sense. We are different. Women often want to feel chosen, relaxed, and emotionally safe. Men often want to feel successful, appreciated, and at ease. Finding the middle ground shouldn’t feel performative. When he leads without pressure and she responds without over-managing or feeling the need to carry the date, both people get to show up more honestly.

Jill Dunn
9 hours ago4 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - January 25 Edition
Have you ever noticed that dating gets frustrating when your focus is on what other people aren’tdoing? That’s the fastest way to feel powerless. They aren’t replying, following through, showing up and it’s so frustrating! I get it! Flip the script. What is in your control is your energy, your consistency, how intentionally you show up, and your ability to stay grounded instead of falling in love with someone’s potential.

Jill Dunn
Jan 264 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - January 18 Edition
January has a way of making dating feel like a full-time job. MORE apps, MORE dates, MORE effort… and somehow LESS clarity. But dating should be FUN, it shouldn’t feel like a HUSTLE. Dating success doesn’t come from grinding harder, it comes from dating with intention, emotional availability, and better discernment.

Jill Dunn
Jan 194 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - January 11 Edition
I don’t know who needs to hear this, but just so you know…you ARE going to meet someone, and when you do, it’s going to make perfect sense why it didn’t work out with anyone else. The person who is right for you is out there getting ready to meet you too, doing their own healing, on their own path, longing for you just the same.

Jill Dunn
Jan 134 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - January 4 Edition
Happy New Year! Andddd it’s “Dating Sunday”…the busiest day of the year on the dating apps. So what does this mean for you? It means activity is high, but discernment is everything.
If you’re logging on today, think quality over volume: update one current photo, send one message rooted in curiosity (not chemistry), or suggest a simple, real-world in-person meet up if the energy is there.

Jill Dunn
Jan 53 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - December 28 Edition
If you’re looking at a New Year’s Eve without someone to smooch at midnight, I want to offer you a little food for thought… not because you’re doing anything wrong, but because maybe you need a little reminder that you’re EXACTLY where you’re meant to be. You don’t actually attract what you want, you know? You attract WHAT YOU ARE.

Jill Dunn
Dec 30, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - December 21 Edition
During this season, I’m wishing you BIG LOVE in whatever way you’re celebrating, or simply moving through right now. A gentle reminder: the quality of your life isn’t measured by what’s missing, it’s shaped by what you choose to notice. There is LOVE around you right now, even if it doesn’t look the way you imagined yet. Let it count.

Jill Dunn
Dec 22, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - December 14 Edition
One of the fastest ways to feel unsteady in dating is to crowdsource your decisions. Too many cooks in the kitchen is never a good thing. Friends mean well, group chats have opinions, and social media is very loud but most advice is filtered through someone else’s history, heartbreak, and blind spots.

Jill Dunn
Dec 16, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - December 7 Edition
So many singles unknowingly treat their love life like they’re waiting for a holiday Hallmark-movie moment… for the universe to drop someone in their path, timing magically aligns, and suddenly it all unfolds perfectly. I’m a hopeful romantic too but… most connections don’t arrive like a holiday miracle. The people who participate, who show up, who put themselves in the rooms where connection can actually happen… they are the ones who reap the rewards (and the relationships).

Jill Dunn
Dec 7, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - November 30 Edition
I have NEVER done this before but, this year has been extraordinary. The connections, the momentum, the growth, the friendships, and the relationships that have formed through the Jillin’ It community have truly blown me away. I’ve been reflecting on the people who show up with courage and curiosity and I want to celebrate and encourage that energy.

Jill Dunn
Dec 1, 20255 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - November 23 Edition
Gratitude as a dating strategy? I DIG! With Thanksgiving this week, I want to offer a reframe for you: GRATITUDE isn’t just a mindset tool, it really is a dating strategy. When you shift from “nothing is working” to NOTICING the people, opportunities, and lessons that are SHOWING UP, your energy CHANGES, your CONFIDENCE rises, and you start ATTRACTING from a place of ABUNDANCE instead of scarcity. It’s amazing how different dating feels when you’re not searching from a defici

Jill Dunn
Nov 24, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - November 16 Edition
We all have a “pattern blind spot” in dating. That one familiar “type” we keep choosing, even when we swear we’ve evolved past it. I can’t tell you how many times someone describes their “ideal partner,” to me and they have unknowingly given me a detailed rundown of their ex. Often times it’ll be the same traits, same energy, same emotional outcome just waiting to happen. That’s a pattern blind spot at work.

Jill Dunn
Nov 17, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - November 9 Edition
Tomorrow morning I take the mic, presenting at the International Matchmaker’s Alliance Conference, speaking on the topic of Events and Authenticity. I’ll be sharing with colleagues how hosting MEANINGFUL events and building AUTHENTIC community can elevate the matchmaking experience for our clients.

Jill Dunn
Nov 10, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - November 2 Edition
Halloween’s over so it’s the perfect time to TAKE OFF THE MASKS… I’m not talking about the costume kind, but the ones we wear on dates and in NEW CONNECTIONS. The right person doesn’t need a perfect connection, they want an AUTHENTIC one. Try showing a little more of your REAL humor, your QUIRKS and your UNFILTERED thoughts. That’s where real connection starts. The masks come off eventually anyways. Just be yourself. Somebody is going to LOVE that.

Jill Dunn
Nov 3, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - October 26 Edition
I believe two things can be true at once. You can feel hopeful about what’s unfolding with a budding connection and still feel the sting of what didn’t work out before. New beginnings don’t erase old endings. Grief and optimism can co-exist. You’re not betraying your choices by honoring your feelings. Read that again.

Jill Dunn
Oct 27, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - October 19 Edition
At our last event I asked singles: “Rate your last date on a scale of ‘marry them’ to ‘block them.’” The answers were… eye-opening to say the least. We definitely had some laughs over the answers but it’s a fun reminder of how different everyone’s dating experiences can be (and why a personalized approach to finding a partner makes all the difference.) You can catch the video on the Jillin’ It Instagram! Some of the stories are pretty unbelievable!

Jill Dunn
Oct 20, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - October 12 Edition
Today marks one year since I lost one of my dearest, lifelong friends suddenly. He was someone who LOVED SO BOLDLY, laughed with his WHOLE BODY, and NEVER missed a chance to tell people how much he valued and cared about them.

Jill Dunn
Oct 16, 20253 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - October 5 Edition
Remember making mixtapes for your friends or crushes? Taking it back to basics, those small, thoughtful gestures have always mattered most. Turns out, a recent Bumble study on dating trends shows that in 2025, singles are favoring micro-romance. It’s the little things. It’s the playlists, the inside jokes, the little “thinking of you” texts over grand, showy gestures that are making a lasting impression. I’m here for it!

Jill Dunn
Oct 6, 20253 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - September 28 Edition
Looks aren’t everything. Who knew, right? According to Bumble’s annual report, dating trends in 2025 show that singles are now swiping more for shared values, emotional depth, and real talk over just a cute photo. However, a new global study found that couples who met offlinereport higher satisfaction, intimacy, and commitment than those who met online.

Jill Dunn
Sep 29, 20254 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - September 21 Edition
Wow! It’s our 100th Singles Sparks annnd it’s my birthday so it got me thinking about milestones. Just like these both mark progress or growth, your dating journey has milestones too. Success in dating is relative. It isn’t only about finding “the one.” It’s also about the first time you felt butterflies again, the first time you said no to someone who wasn’t right, or the first time you asked for what you really wanted. Those wins deserve to be CELEBRATED too!

Jill Dunn
Sep 22, 20254 min read
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