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Singles Sparks - CT and NY Matchmaker Insights for Singles - September 13 Edition
One of the most confusing dating situations isn't when someone is treating you badly. It's when they seem to like you, things feel good and you still don't know where you stand. But before you have the "clarity conversation" remember, it isn't only about asking... "Do you want to commit to me?" You MUST first ask yourself "Do I want to commit to this?"

Jill Dunn
4 days ago4 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - September 6 Edition
At some point, you do have to wonder if it's really EVERYONE ELSE. A client said something to me this week that I LOVED. She's been meeting men who check so many of her boxes... same stage of life, divorced with young kids, desire for a blended family, successful, active, emotionally ready for a relationship. But she simply hasn't been attracted to them. And after this happened a few times, she stopped and wondered: "Wait... do I just not find men attractive anymore?"

Jill Dunn
Sep 94 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - August 30 Edition
I realize some of the dating advice I give works especially well in matchmaking because I have the advantage of talking to both people. I know he likes her but doesn't want to come on too strong. I know she likes him but is waiting for him to make the next plan. I can see when two people who actually like each other are overthinking, misreading each other, or about to get in their own way.

Jill Dunn
Aug 315 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - August 23 Edition
I'm ALL FOR honesty in relationships. This isn't permission to lie, hide something important, or be deceptive. But honesty doesn't mean giving someone immediate access to every chapter of your life. So many pieces of your past made you who you are today: relationships, heartbreaks, mistakes, lessons, ALL OF IT. Revealing those pieces too quickly can mean sharing them before someone has enough context to understand who you became because of them.

Jill Dunn
Aug 244 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - August 16 Edition
I just got back from an incredible trip through the Grand Canyon and Antelope Canyon, and standing inside those massive, perfectly sculpted walls, I kept thinking about what created all of this gorgeousness. Water. Not force. Not pressure. Just water. Slowly. Softly. Simply by continuing to flow.

Jill Dunn
Aug 174 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - August 9 Edition
August is giving you an advantage, so use it. People are outside, social, traveling, gathering, feeling good, feeling tan, feeling finnnnne. Dating doesn't always have to mean another app, another singles event, or another scheduled first date. Sometimes it's simply being a little more awake to who's already around you.

Jill Dunn
Aug 104 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - August 2 Edition
Have you ever asked yourself..."If the right person walked into my life tomorrow, would I truly be ready for them?" We spend so much time evaluating everyone else - their communication, their emotional availability, their effort - but we rarely turn the mirror around and ask how we're showing up. Before you ask, "Where are all the good ones?"ask yourself a more powerful question: Am I becoming the person I hope to find?

Jill Dunn
Aug 24 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - July 26 Edition
Last weekend, I had the incredible privilege of celebrating the wedding of one of my matchmaking clients. Watching him marry the woman he calls "the love of my life" was a beautiful reminder of why I do this work.

Jill Dunn
Jul 274 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - July 19 Edition
When I noticed that this week's newsletter is Issue #143, it instantly transported me back to a much simpler time. Long before emojis, texting, and dating apps, "143" was a simple shorthand for "I love you." It had been passed around in notes and conversations for years, but the pager era made those three little numbers iconic.

Jill Dunn
Jul 205 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - July 12 Edition
As I'm writing this tonight, I'm sitting in my backyard watching fireflies dance across the lawn. They're beautiful, aren't they? Magical, even. But if you've ever tried to catch one, you know what happens. You run from one little flash of light to the next, only to watch it disappear and pop up somewhere else.

Jill Dunn
Jul 134 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - July 5 Edition
If there's one thing I wish for you, it's that you don't wait until you're in a relationship to celebrate the LOVE in YOUR LIFE. Yes, my work is to help people find LOVE, and I believe deeply in the beauty and importance of partnership. But I also believe this: your life deserves to be celebrated now, not someday. The relationships you nurture with friends, family, your community, and most importantly, with yourself, are all part of your beautiful life of love.

Jill Dunn
Jul 84 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - June 28 Edition
Everyone wants the outcome. Few people appreciate the process. But the process isn't just getting you to the relationship... it's preparing you for it. I was thinking about that tonight as I wrapped up a full Saturday. Time with my kids. A challenging inversions workshop at yoga (new for me... and so much fun!). Four-plus hours updating my website and clearing my inbox. And now, well after midnight, sitting down to write this newsletter before it lands in your inbox in just a

Jill Dunn
Jun 294 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - June 21 Edition
Serious question. Why is it that we sometimes treat the people we're meeting and dating with less courtesy than we give complete strangers. Think about it. If the electrician calls and leaves a message, we call them back. If the clerk at the store goes out of their way to help us find something, we thank them. If a neighbor stops to ask about our dog, we smile and answer.

Jill Dunn
Jun 234 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - June 14 Edition
This is something that comes up a lot: "How often should we be talking?" or "She hasn't texted me all day. Is that normal?" or "Should I text him first?" And I get it! Early stage dating can be anxiety inducing. My answer is almost always the same: If you like someone, communicate about how you communicate.

Jill Dunn
Jun 205 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - June 7 Edition
One of the hardest (but most important) lessons I learned when I started dating after my divorce (10 years ago!) was that I was holding new people I met to husband standards. No wonder I was always disappointed!

Jill Dunn
Jun 84 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - May 31 Edition
One thing I notice over and over again is that men and women usually describe what they want very differently, but when you peel back the layers, they're usually looking for the same thing.

Jill Dunn
Jun 24 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - May 24 Edition
Quit playing it cool. OK? One of the biggest dating misconceptions is this idea that you can have the deep intimacy that you desire while avoiding vulnerability. You can’t. I see this constantly. People want closeness, CONSISTENCY, emotional SAFETY, reassurance, and PARTNERSHIP… but at the same time they’re pretending not to care, holding back emotionally, and trying so hard to “play it cool” that nobody actually knows how they feel.

Jill Dunn
May 254 min read


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

Jill Dunn
May 184 min read


Singles Sparks - CT and NY Matchmaker Insights for Singles - May 10 Edition
I spent this past week in NYC at the Global Love Institute conference with 150+ dating and relationship professionals from around the world, and I have to say… one of my favorite parts of this work is the incredible community of colleagues I’ve come to know, love, and collaborate with. I can't even count how many client-to-client matches I left there ready to present to my private clients. My heart (and to-do list!) is so full!

Jill Dunn
May 114 min read


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

Jill Dunn
May 55 min read
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