A Gilmore Girls' Guide to Dating: Part One

How to Find the Right Person… and then What to Say


Luke and Lorelai finally on their first date

First published 12 Mar 2013

We loved the banter, the hijinks and the serious family dysfunction. But come on. Gilmore Girls is all about the relationships. The family. The friends. And the dating. Lorelai and Luke, Rory and Logan, Lorelai and Max, Rory and Jess, Kirk and Miss Patty… the list goes on – the last one may have been a spray-cheese-induced hallucination. So walk with me won’t you, as I take a lighthearted look back down Lover’s Lane – possibly by way of Lane’s lovers – ladies and gentlemen, for your delectation… Part One.

I: How to Find the Right Person… And Then What to Say

If you’re a Gilmore Girl, the number one spot to pick up guys is easy: School.

Obvious perhaps for school-age Rory, but Lorelai also nearly picks up a single dad as soon as she walks through the Chilton gates. And shortly thereafter meets Max Medina, Rory’s teacher. As if cruising for Dishy Dads wasn’t enough, through her adult education classes and seminars, she meets both Alex – the guy setting up a coffee house – and Paul, the young looking fella from her business class who turns up at Luke’s with his parents. Plus of course she got extra-curricular with Chris, finishing high school summa cum Rory.

The number two spot? Any place serving coffee. From Luke’s to a Harvard coffee cart.

Introductions through friends or family can work out well – or not. Emily springs Chase Bradford (‘Connecticut Ken’) on Lorelai, an unwanted blind date so awful that Richard helps her escape from the bedroom window. But it can work out better, like Jason ‘Digger’ Stiles who, while not her type, showed that it can be worth venturing outside your comfort zone. For Rory too, Jess and Logan were both friends of the family and you should always check outside your dorm room corridor for someone like Marty, passed out and naked.

It’s a sad fact that after leaving school, opportunities to meet new people decline dramatically. Approaching strangers and asking if they want to be your friend can be unsettling for everyone involved. Or at worst, become grounds for a restraining order. In this situation, follow Lorelai’s lead so that when an opportunity does present itself, you can make the most of it:

1) Be yourself. Is Lorelai ever not herself? Admittedly, few of us are blessed with her gifts for word vomit, quick wit or a gorgeousness that could launch a thousand ships – but being yourself is paramount. If you’re not being yourself, you lose two ways. First, if your potential mate likes the you you’re pretending to be, they’re not liking you; and second, if you do end up together, you’ll constantly have to be someone else. If your potential mate doesn’t like you, being yourself, you can do better.

(A sidenote – I did read somewhere that in applying effort to ‘be yourself’, you’re actually not being yourself, you’re being the version of you that you want to be. I’m not sure there’s much you can do about that, but just saying.)

2) Follow your own path. In following her own interests, Lorelai puts herself in the path of opportunity, both work-wise and romantically. Until she meets Max, Lorelai has kept Rory front and centre, never bringing a guy home or allowing her two worlds to collide. It’s only when Rory begins Chilton that Lorelai begins to relax. With Rory firmly on the right track, we see that Lorelai starts to encounter people in similar situations and with similar priorities; and is able to act on them. For example, Max Medina, a bona fide Proust-owning bachelor nimble enough to skip around desks when keeping polite distance - but man enough to throw them over should the need arise.

3) Above all, be open to opportunities. Sometimes the most obvious candidate can be staring you right in the face. Serving you coffee from behind a counter. Or watching you moodily from the bleachers. Your greatest admirer might be someone who just loves being around you being you.

… So next, what to say?

Lorelai and Paul

In order not to lose it like Rory’s first encounter with Dean, take a look at Lorelai and Paul as a case study. He’s the guy from Lorelai’s business class who was younger than he looked. You know, this guy:

Rory jibes Lorelai "I've always wanted a little brother"

Yes, he’s a trifle obscure but indulge me… he asks to borrow her notes and they bond over a vending machine burrito. He opens cannily, at once both engaging and provocative – in the sense that his opener invites a response and respond, she does:

Paul Once again ladies and gentlemen, she takes the last burrito. Lorelai And hello to you too. Paul Week after week, how do you do it? Lorelai I told you, correct change. You go in for that dollar bill nonsense, you’ll be standing there for ten minutes watching it. Ehhh. Eh eh eh. s02e09 Run Away, Little Boy

No doubt here, she’s being herself. When she finally takes his digits, she opens herself up to both companionship and a truckload of gentle town ridicule.

(Regarding his continued borrowing of her notes, there’s good evidence to suggest that people will like you more if you ask them for favours, rather than if you do favours for them. The so-called Ben Franklin effect works because we don’t like our thoughts to contradict our actions, so the helper subconsciously want to continue helping. Bear in mind that asking for too much could cause the opposite reaction but don’t say we never tried to teach you anything here.)

Lorelai and Max

Lorelai arrives late to Max’ curriculum meeting with the pupils’ parents. She’s herself, clumsy and caffeinated. He’s charming, romantic and demonstrates himself to be kind and attentive, without going overboard. Of course he’s smitten with her, who wouldn’t be? Good first impressions all round.

Lorelai stumbles into Max' world

Lorelai [retrying the school coffee] It… it just keeps getting worse. Max Well you know not drinking it is always an option. Lorelai Not in my world. Max I’m Max Medina. Lorelai Nice to meet you. s01e04 The Deer Hunters

And later on, after Rory gets hit by a deer and misses the test, Max leaves a sympathetic answerphone message, tacking on a message for Lorelai:

Max And if your mother is listening, Lorelai, it was a pleasure encountering you. I hope it happens again.

Note to self: Never answer the phone when Max Medina calls because you’ll be able to live off the warmth of his adorable answerphone messages for the winter.

Lorelai and Alex

Sookie and Lorelai attend a business seminar to be seminarred about business. They bump into Sookie’s old chef friend Joe and his (business) partner, Alex. Heaven forbid Lorelai be out-conversationed by Sookie and Joe so she makes up her own ol’ buddy history, strong-arming Alex into playing along:

Lorelai Hey, remember the time you and Fat Sal got locked in the freezer overnight? Alex Fat Sal? Lorelai Work with me here. Alex Oh, Fat Sal, yes, right. Sookie (to Joe) Then Feldman got into a fight with the bride’s mother. Joe (to Sookie) That’s right! He went after the whole bridal party. Lorelai And you remember how me and the Bruiser – Alex … never liked that guy. Lorelai We found you and Fat Sal in the morning and you were frozen together like bacon. Alex Yeah. You know, I still can’t eat bacon. s03e11 I Solemnly Swear

With new people, Lorelai is like-it-or-lump-it: This is how I am. She’s like a Tasmanian Devil and you can’t help but get caught up at the edges of her. A force of nature. Sure, Alex was never a serious contender and didn’t have the strongest of starts but he’s a good date, which we’ll see later on.

Lorelai and Jason

Lorelai meets Jason ‘Digger’ Stiles a full three episodes after his initial introduction as Richard’s new business partner. It’s an foreshadowing worth of Pacino in The Godfather. Also a re-introduction for the two of them, having known each other from summer camp as kids. Their reunion as grown-ups sees her demanding a pound of flesh for his arranging a business client trip to Atlantic City, rather than Emily’s idea of a cocktail party.

Jason Well, I had no idea how much chaos my little weekend was causing. Lorelai No, you didn’t, because you didn’t think. You never thought. Back in summer camp, you never thought. “Hey, if I stand up in this canoe, maybe it’ll tip over.” That was the extent of your thought process. Jason You’re still mad about that. Lorelai I was fully dressed. Jason I remember – green T-shirt, no bra. Lorelai What? Jason Trust me, I was the hero of cabin five for the rest of the summer. s04e06 An Affair to Remember

During the same argument, he blindsides her by asking her on a date. Despite her anger she very nearly says yes because of how much Emily would hate it. This is why he’s my favourite. He’s not her obvious type yet they have a quirky chemistry. He can keep up.

Lorelai and Luke

While we never actually witness their first encounter, Luke recalls it on their first date. We’ll get to the date itself in due course, but here’s his recollection, in all its glory.

Luke It was at Luke’s, it was at lunch, it was a very busy day, the place was packed, and this person - Lorelai Ooh, is it me? Is it me? Luke … this person comes tearing into the place in a caffeine frenzy. Lorelai Ooh, it’s me. Luke I was with a customer. She interrupts me, wild-eyed, begging for coffee, so I tell her to wait her turn. Then she starts following me around, talking a mile a minute, saying God knows what. So finally I turn to her and I tell her she’s being annoying – sit down, shut up, I’ll get to her when I get to her. Lorelai Y’know, I bet she took that very well, ’cause she sounds just delightful. Luke She asked me what my birthday was. I wouldn’t tell her. She wouldn’t stop talking. I gave in. I told her my birthday. Then she opened up the newspaper to the horoscope page, wrote something down, tore it out, handed it to me. Lorelai God, seriously. You wrote the menu, didn’t you? Luke So I’m looking at this piece of paper in my hand, and under “Scorpio,” she had written, “you will meet an annoying woman today. Give her coffee and she’ll go away.” I gave her coffee. Lorelai But she didn’t go away. Luke She told me to hold on to that horoscope, put it in my wallet, and carry it around with me – one day it would bring me luck. [Luke pulls a small scrap of paper from his wallet and holds it out to Lorelai] s05e03 Written In The Stars

It is actually killing me to not include the next lines after that. Once again, you get the feeling she knows there’s nothing to lose by losing yourself in the moment.

Next week, Part Two: The Pre-Date, something Kirk could teach you a thing or two about.

Kirk raises a glass to his imaginary pre-date