I am a person, like many in my generation, who is hypervigilant of timing, especially in situationships: How long until they text back? How soon is too soon to make the first move? How long do I have to wait until I can 'rebound'?
Dating follows this train of thought. I am sure there are many 'ideal' times to start dating, but I have wondered what the best time to start dating truly is. After consulting others in long-term relationships, and a few too many scrolls on TikTok, I have concluded that the best month to start dating is September.
September carries a kind of magic that few other months can match. It’s a season of fresh starts and clean slates, a time when people are ready to hit reset after the hazy chaos of summer. The launch of a new school year—or simply a new routine—creates a sense of structure and possibility that makes getting to know someone feel more intentional.
Summer romances are often spontaneous but fleeting, and winter flings can be clouded by seasonal depression and fake resolutions that fade by February. But September relationships have room to grow steadily, to develop alongside the rhythm of falling leaves, cozy nights, and the anticipation of the holidays ahead. In other words, September isn’t just another month on the calendar—it’s the perfect backdrop for something real to begin.
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In order of events and holidays (depending on your religion, of course), September allows for the perfect amount of time to start a relationship.
As the air gets slightly crisper, your relationship grows fonder. Pumpkin patch dates are on the calendar, and of course, a carving contest (if you are competitive like me). Gilmore Girls is playing on the TV while the two of you pick out your couple's costume for Halloween.
Bonus if you like watching scary movies (great way to build some tension!) The leaves are falling, you get to wear their sweatshirt, while making s'mores next to the bonfire. It is new, exciting, and fresh.
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This then leads to thanksgiving. Assuming you are still together, you will be coming up on almost three months. Ideally, you are falling in love with this person, meaning it is time to bring them home to meet the family.
They meet the parents and bond over shared likes and dislikes for football teams. Thanksgiving, being an intimate family holiday for most, will serve as the first test of where this person fits into your life. It allows the parents to 'approve' before getting too serious.
It also allows for your partner to be put into the middle of family dynamics; you can see how they react when your family gets into a heated debate over politics at the table. If they can weather the storm of family drama, then you know they can stick around for more.
Then we come up on my personal favorite holiday: Christmas. Your time is spent in matching pajamas while baking cookies and watching Love Actually. If lucky, you can participate in a snowball fight, but most importantly, the "gift-test" is presented.
What will they get you? Will it be a necklace? Do they pay attention to whether you wear silver or gold jewelry? It can be a make-or-break moment, especially if your love language is gift giving. It is the perfect holiday for any romantic out there.
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Then we approach New Year's: you are in love, ready to jump into a new year with this person. You get the opportunity for a midnight kiss while starting to seriously envision a future together. All of this culminates in a recipe for a healthy relationship, barring no breakups or heartbreaks. So, if you are a hopeless romantic like me who craves an epic love story, September is the time to enter chapter one.
