The people of Stars Hollow are about to be walking in a winter wonderland, but first we find Lorelai and Rory at a town meeting, where everyone seems to be arguing over petty matters that the Gilmore girls find highly amusing. The mayor, Taylor, is admonishing the Stars Hollow residents about leash laws before he begins talking about the anniversary of the legendary Stars Hollow battle. Apparently, the town even has an annual reenactment of the battle. The whole reenactment issue infuriates Luke, who demands that the whole charade stop. He says that the battle never happened, they are glorifying a war they never fought to keep land that they originally stole anyway. It is not surprising that Taylor is not pleased with Luke's comments.
Later that night, Lorelai wakes up because she can smell the season's first snowfall in the air. There also happens to be a surprise message on the answering machine. It's from Max, Rory's English teacher at Chilton, and he wants to know if he and Lorelai are ever going to go on a date. Lorelai is clearly smitten and plays back the message again and again to hear Max's voice.
In the morning, while dressed in her marching band uniform, Lane tells Rory about meeting her soul mate at school. Rory doesn't hear a word coming out of Lane's mouth; she is too distracted, thinking about her boyfriend Dean. She stops by the Inn to grab Sookie's homemade rocky road cookies before heading to the bus stop. Lane follows, but then leaves when Rory and Dean begin to get all mushy. Lane feels left out because she is the third wheel.
Meanwhile, it is Friday night and the snowstorm is brewing. It is already hitting Hartford, where Emily and Richard live, so Lorelai is going to have to skip their weekly dinner. Rory arrives at her grandparent's house right after school and finds she is stuck at her grandparents without her Mom. No big deal though, Rory will just have to make the best of it. As for Lorelai, she is walking through town enjoying the first snowfall of the year. She finds Luke, who is still cranky over the battle reenactment. They watch together as the old men of the town gather in the cold with their muskets while the school's band sets up to provide a little music. Lane, mesmerized by her crush Rich, then does the unthinkable. She stares at his hair and actually runs her fingers through it! When Rich gives her a look like, "What are you doing?!", Lane bolts in total humiliation.
Cutting back to Lorelai, she is surprised and delighted to runs into Max, whose car has broken down in Stars Hollow. With Rory away for the night, the two can finally have their first date.
Over at the grandparent's house, Emily is in a tizzy because Florence, the cook, cannot make it to work. Now, what are they going to do? Rory offers to check the refrigerator and whip something up. (Emily's never whipped up anything in her life.) Rory strikes gold when she spots a frozen pizza putting her grandmother in shock. Emily then declares that the pizza must belong to the maid. After all, that is what you eat at a carnival or a Turkish prison, according to Emily. Rory decides to play chef and banishes the grandparents from the kitchen. Then, while the pizza cooks, a curious Rory goes up to her mom's old room and does a little snooping, where she finds a strip of pictures from 1983 of her mom and dad kissing. Rory gets a bit bummed out seeing her folks at a time when they were totally in love. Rory decides to call home, but it is Lane who answers the phone. Lane had run to Rory's house after the "Rich incident" and now she is freaking out. She lays into Rory about what a bad friend she has been. Rory apologizes but it is a day late and a dollar short. Then, the phone goes dead, leaving Lane high and dry, and Rory feeling like a total jerk.
Meanwhile, Lorelai and Max walk and talk in the snow, flirting and generally charming the pants off each other. Lorelai brings Max to a cozy café where they show old horror flicks, and it is right there on the couch where they share their first kiss. When the pizza is ready, Emily and Richard dig in, and thanks to a little doctoring with some fresh Parmesan cheese, it is a big hit. After dinner, they all look at some old photos and find Lorelai dressed up in a debutante gown. The conversation immediately gets awkward because Lorelai never got to be an actual debutante because she got pregnant with Rory.
Back in Stars Hollow, Luke feels bad and brings the freezing men some hot coffee while they wait out their reenactment. His good deed backfires when he witnesses Lorelai and Max walking back to the Gilmore house and looking all chummy. He then sees them kiss and the look on Luke's face says it all. Once at the house, Lorelai does not want to let Max in. She has never brought a man home before out of respect for Rory. And she does not necessarily want to start now. But it is snowing so hard, and Rory is away for the night, so Lorelai breaks her own rule, letting Max over the threshold.
They are barely in the house when they start making out like teenagers and start making their way up the stairs. But then their hot and heavy session is interrupted when Lane appears out of nowhere. She apologizes, then bolts back into Rory's room and blasts loud music. A big signal for help, Lorelai sends Max into the kitchen and goes to Lane. Lane gives Lorelai the lowdown. Lorelai basically says it is not a big deal, everyone screws up in high school, it is how you handle the experience that matters. Lane feels better after the pep talk, and Lorelai goes back to Max. Lane is now spending the night, so any hoochie coochie between the two is off limits. Max stays the night too, but on the couch and settles for a goodnight kiss.
The next morning, Rory comes home early from her grandparent's house. Lorelai heads her off at the door and comes clean fast. Rory is definitely weirded out by the situation and asks her mom if she is in love with Max. Lorelai says she likes Max a lot, but it has only been one date so she cannot tell. But Rory is quick to point out that Lorelai has never let a man in the house before. Lorelai admits she had a great time with Max and only time can tell if he is the right one. Next, Lane comes out of Rory's room, and Rory apologizes for being an awful friend. Rory swears that Lane is not a third wheel and announces that Dean will just have to deal with the fact that Lane came first. They plan for coffee later and then Lane bolts, leaving Rory with her mom and Max. She is about to join them in the living room, but sees they are sipping coffee and decides, instead, to hang solo in the kitchen. As the show ends, Rory pulls out the pictures of her mom and dad and looks at them one more time.
- Everything's magical when it snows. Everything looks pretty.
- – Lorelai
- First mention of Richard's ex-fiancé, Pennilyn Lott, here called Lynnie Lott.
- Lorelai hasn't brought a guy to her house before.
- Also first and only mention of Emily's sister, Hope, who lives in Paris.
- The introduction of Star Hollow's town meeting.
- Jane Austen (Northanger Abbey)
- Hunter S. Thompson
- Charlotte Bronte
- Judy Blume
- Emily Dickinson (Max Medina mentions in his voicemail that he is grading a paper on Emily Dickinson)
- Lorelai – (to Rory) Hey babe, (to Lane, nods) Sergeant Pepper
- Emily – A bad storm is heading your way. It’s already hitting us here.
- Lorelai – Well, don’t panic. I’ll get the ark, you get the animals.
- Lorelai – I'm making a point, Mouthy McGee. (Referring to Gil Thorpe comic strip character)
- Lorelai – Well, uh, gee, Mom, I don't know. Let me see… black ice, treacherous roads. I'll just put on my red, white, and blue leotard, grab my golden lasso, and fly the invisible plane on over?
- Lorelai – All right, honey, tell Grandma you arrived there not a member of the Junior League, I'd like you to leave there the same way.
- Max – A match made in Heaven.
- Lorelai – or in Bellevue
- Richard – You also knew that you wanted to marry Errol Flynn