September: The Perfect Month to Start Your Next Love Story
September has always been my month. Not just because it’s my favorite time of year, but because so many of my life’s biggest turning points happened right around this time. In fact, I believe September is the perfect month to get back into the dating scene. And I have decades of personal proof.
It might sound strange to be so attached to a month, but when you’ve had as many pivotal moments in September as I have, it becomes something more than a date on the calendar. It becomes a season of possibility.
September & My Milestone Moments
The half-birthday tradition that started it all – Growing up, my mom made a big deal about my half-birthday every March 6th–a cupcake, a candle, and a reminder to celebrate life’s little milestones. Maybe that’s why I’ve always looked at the calendar and thought about moments that matter… and for me, September is full of them.
A Cross-Country Adventure of a Lifetime – After undergrad at UVM, my first job as an environmental educator took me to Illinois (Lake County to be exact). But after a year, my heart was set on something bigger. I spent that month on an epic cross-country road trip with one of my best college friends. We camped, visited 13 national parks, and stayed with friends along the way.
The trip ended with her drop-off at LAX so she could fly to New Zealand to see if things would work out with a Kiwi she’d met traveling earlier that year. (Spoiler: they did! She married him, and they’ve been there ever since, with two kids now in their twenties.)
Santa Barbara Beginnings – The day after I dropped her off, the plan was to meet another one of my UVM besties in Santa Barbara, CA. We each knew one person, had no jobs, no apartment, and only our mutual sense of adventure to guide us. At 23, that was enough. We figured it out… and those years in SB were golden.
San Francisco Calling – Fast-forward five years from that leap-of-faith move to Santa Barbara, the Bay Area tech boom was booming. In 2000, I packed up once again and headed north to San Francisco, arriving on October 1st with the same mix of excitement and uncertainty I’d felt at 23. Santa Barbara had given me five unforgettable years, building a community from scratch, forging lifelong friendships, surviving a few big break-ups, and learning how to create a life I loved in a place where I initially knew almost no one. San Francisco was a whole new adventure: a bigger city, a faster pace, and a thriving cultural scene. Plus, it was the land of blind dates set-ups by everyone and their mother (literally). It was another fresh start that would shape the next chapter of my life in ways I couldn’t have predicted.
A Back East Return –Twelve years later, I felt another September pull… this time to make a bigger change than just a job shift. Leaving a piece of my heart in San Francisco, I moved back east to Washington, D.C., to be closer to family. My mom flew out to drive cross-country with me, though this time in just six days with only a few fun stops, landing in D.C. the last week of September.
The September That Changed Everything in Love – In September 2017, six months after losing my dad, I felt ready to date again. I joined Bumble for the first time, and as “fresh meat” on the app, I quickly had a few promising conversations. One of those dates was on Friday, September 22—a post-dinner drink at Liberty Tavern in Arlington, VA with a man named Ori. Six years later, almost to the day, we got married… on September 30, 2023.
Why September is the Perfect Dating Month
I’m not the only one who believes in September magic. It’s backed by modern dating trends:
Singles are re-engaged after summer travel and distractions.
Dating app activity spikes — people are back to routine and ready to meet someone.
Fall events and cooler weather make for cozy, low-pressure date ideas.
It’s a season of momentum — not just in your social life, but in the way people show up for connection.
Your September Love Story Could Start Now
If you’ve been thinking about getting back into the dating world, here’s my advice: don’t wait until January. September is hands-down the best time to start fresh. As I’ve shared, for me, September has always been a month of new beginnings, big moves, and life-changing moments.
Your future self will thank you for starting now.
Let’s make this your September to remember. Whether through my Match Me services, a dating strategy session, or by joining my Date-A-Base of singles ready for serious relationships.
Ready to start? Click here to get in touch. Matchmaking and coaching spots are open just in time for the September surge.
