Don’t you just love September weather? It’s one of my favorite times of year for sure. Crisp air, fresh starts, and a little tug on the heartstrings that always comes with change. Seasons shift in nature, but they shift in our lives too… especially in our dating lives. Every season of dating whether it’s a string of first dates, a tough breakup, or the sweetness of a thriving relationship carries its own wisdom.

Repeat after me: “Cuffing is CANCELED!” Cuffing Season is the time, usually from October to February, when some singles seek out short-term relationships for comfort during the colder months. As this season approaches, it’s easy to get swept up in temporary comfort but PLEASE remember, settling for convenience isn’t the same as building something real and more than anything it is just pushing off your potential to meet your FOREVER partner.

It’s the unofficial end of summer and the start of the busiest season of the year for matchmakers. In September, Summer flings fade, routines reset, and singles are more serious than ever about finding love and (fun fact!) it also happens to be National Matchmaker’s Day. If you’ve been thinking about working with a matchmaker, let me tell you, now IS the time. At the very least, make sure you’re in my free database while the season is heating up.

Swipe fatigue is real but singles are going to the extreme and literally going rogue. People are starting to date robots. Read that again. AI can write your profile and even play the part of a “perfect partner,” but it can’t give you butterflies across the dinner table or hold your hand.

So often, I see singles get caught up in the chase of being liked on a date that they forget to ask the much more important question: Do I actually like them? When your energy is spent trying to impress and share all of the amazing and impressive things about yourself you miss the chance to feel whether this person aligns with your values, your lifestyle, and your heart.

Keeping your head above water in the dating POOL can be exhausting. I get it. Every date or relationship that isn’t “the one” can seem like a failure and another reason to give up but I’m begging you to ZOOM OUT.

Breakups are always hard but breaking up with someone you thought was the one can feel like losing the future you imagined (or like an elephant is sitting on your chest.) Relatable? What does it really take to heal, rebuild, and open your heart again?

There are no hard and fast RULES for the early stages of dating that would apply to everyone. There truly is a lid for every pot but a first date conversation that excites one person may be a huge turn off for someone else. BUT with that said, there are so many times that I hear clients telling me about things that were said on first dates that make me CRINGE because they really just tank the vibe unnecessarily.

Most singles have a love/hate relationship with dating apps. Let’s be honest, it’s usually more hate than love. Sure, they’re convenient, but they often lead to burnout, ghosting, and connections that fizzle fast

Most singles have a love/hate relationship with dating apps. Let’s be honest, it’s usually more hate than love. Sure, they’re convenient, but they often lead to burnout, ghosting, and connections that fizzle fast

Did you get enough of the fireworks on the 4th? Ok. Good. Because in dating, we’re often told to chase that same spark, instant chemistry, butterflies, the “wow” factor right away. But here’s the thing: real, lasting connection often starts quietly.

“I am nervous about this date being a fail.” I just got this text message from a Matchmaking client about an upcoming date and believe me, I GET IT!  That is a very common worry. My response: “A date is never a failure!

What if the way you’ve been dating is actually keeping you from the love you want? Hard to imagine. Right? On Saturday, Jillin’ It LoVe CluB members tuned for a conversation on how to “Date Like You Mean It: The Blueprint for Finding Real Love.” We explored how intentional dating, emotional availability, and aligned actions can transform your love life. It was a powerful reminder that real connection starts with showing up as your most authentic self. The ACTION that you take

It’s Father’s Day. This can be a happy day or a sad day for some but ultimately it can be a reminder of the love, strength, and guidance that shape us and the kind of partner we hope to find or become.

Coffee anyone? Coffee dates often get a bad rap, but they’re actually one of the best ways to get to know someone in a low-pressure, authentic setting. They create a relaxed, uncomplicated environment where both people can truly focus on conversation.

Here’s my PLEA for a 2nd date: If I had it my way everyone would consider every first date a two-part experience. Date One is just the vibe check. Awkwardness, nerves, and surface level conversation are totally normal and can sometimes get in the way of seeing something amazing under the surface.

Got questions about DATING? You’re in luck! I'll be LIVE on the Christine and Salt Show on 96.5 TIC this Wednesday at 8 AM, answering your questions live on air! Call or text your dating dilemmas to 860-247-9696 and yours may get answered. Can’t wait to chat with you!

Something hit to me this week as I’ve been considering candidates for different support roles here at Jillin’ It. It occurred to me how much dating is actually like hiring. You’re “hiring” for the most important position in your life. So, you should date like you're hiring: don't just look for chemistry, look for character. The elusive “sparks” are fun, but it's shared values, communication, and consistency that build real relationships.

Celebrate Mother’s Day with heart and humor in this week’s Jillin’ It newsletter. Dive into the science of attraction, spot the top signs someone’s not over their ex, and meet a thoughtful bachelor in our Singles Spotlight. Don’t miss our May 23 rooftop Singles Mixer or your chance to join the FREE Date-a-Base for personalized matchmaking. Join the Jillin’ It Love Club for exclusive access, roundtables, and more ways to spark real connections.

Join the Jillin’ It Love Club for expert matchmaking, exclusive singles mixers, and weekly insights to help you build lasting love. This week’s spotlight features a new rooftop event, signs your relationship may have lost its spark, and why healthy relationships sometimes feel “boring.”