A Gilmore Girls’ Guide to Dating: Part One – How to Find the Right Person… And Then What to Say


A Gilmore Girls’ Guide to Dating

We loved the banter, the hijinks and the serious family dysfunction, but the first thing that comes to mind when recollecting Gilmore Girls is the relationships: Lorelai and Luke, Rory and Logan, Lorelai and Max, Rory and Jess, Kirk and Miss Patty… the list goes on – although that last one may have been a 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'm all in

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 not long after that she 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.

The thing is, after you leave school and start working, opportunities to meet new people decline dramatically and going up to 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 can start 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 Proust-friendly 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 then, 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:

i 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.
(so2e09 Run Away, Little Boy)

No doubt here, she’s being herself and 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 some psych that suggests people 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 when we help someone out, we subconsciously want to continue helping. Sure, you could easily go overboard and 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.

what in the 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, he leaves an answerphone message saying she can make up the credit, thoughtfully including 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 ever.

Lorelai and Alex

Sookie and Lorelai go to a business seminar to be seminarred about business and bump into Sookie’s old chef friend Joe and his (business) partner, Alex. Heaven forbid Lorelai be out-conversationed by Sookie and Joe and 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: Then Feldman got into a fight with the bride’s mother.
 – Joe: 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, like 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, Pacino-style, a full three episodes after his initial introduction as Richard’s new business partner. It’s a re-introduction since they knew each other at summer camp and their reunion as grown-ups sees her demanding a pound of flesh for his arranging a client trip to Atlantic City, over Emily’s 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 asks her out on a date and she only says no because she’s mad and she very nearly says yes because of how much Emily would hate it.  This is why he’s my favourite, he’s not her type yet he gets this close to talking himself onto a date with her.

Lorelai and Luke

While we don’t get to see 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: [grinning] 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 – [pulls a small scrap of paper from his wallet and holds it out to Lorelai] one day it would bring me luck.
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 everyone a thing or two about.

sweater to crumb ratio

 All pictures courtesy of the WB



Rich originally began contributing to GIlmore News as 'Dairyman' in 2013, a reference to the character Dairyman Dick in Tess of the D'Urbervilles, (call me Rich). Here in the UK we were late to the Gilmore party and I don't remember what made me watch my first episode - the one where Lorelai picks Rory up from the police station after she and Logan steal a yacht - but I remember watching it again immediately. And then again. Thankfully, the next show was on the next day and I watched that one three times too. And then the boat one again. I couldn't believe the dialogue was so quick and so funny and I pretended to myself that I was only watching it so I could figure out who I was more keen on - the mom or the daughter. I swore that Aaron Sorkin must have been involved but I couldn't find his name attached anywhere, even on the internet. So I watched and loved and laughed and cried and the day after the series finale, they ran the entire show from the beginning again and Rory turned into a baby so then I was all about Lorelai. Lauren Graham is astonishing ("Mother: Breathtaking") and the show was - and is - lightning in a bottle. It's a treasure for those who watch and get swept up in it, like I did and like the readers of Gilmore News. It's heartbreak and chicken soup, family dysfunction and blind optimism, lighthearted romanticism and balls-out brilliant. Thanks to Arieanna and gilmorenews.com for letting me squat and allowing my inner Gilmore Geek out for air. I worry how it would otherwise manifest.

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