A Gilmore Girls’ Guide to Dating: Part Two – The Pre-Date


In the Gilmore world, how do you get from being interested to actually dating?  

Pop Quiz: Who’s this, asking Lorelai out?

?: We’ve known each other for a good amount of time and our paths have crossed, professionally and socially a number of times all with relatively pleasant results and, well, I was just wondering if you would like to have dinner with me.
Lorelai: Oh.
?: In two weeks.
Lorelai: Two weeks?
?: I heard you have a cold, I think two weeks is enough to ensure the virus is out of your system.

Answer at the end.

all in

So, there’s this potential guy or girl, you’ve watched her from afar, say, sitting under trees reading books or in band practice and you really want to touch his hair (do NOT touch his hair). What next?

Well friends, it’s Part 2 of the (really just an excuse to re-live some of the warm and fuzzies) Gilmore Guide to Dating.

II: The Pre-Date

What’s a pre-date? I’ll hand over to the expert, Rory’s high school teacher Mr. Max Medina. He’d only met Lorelai a couple of times and the second time was to tell her that Rory couldn’t sit the test that they’d revised for all week until they overslept at the kitchen table. So now it’s the Chilton school bake sale and he pulls Lorelai aside and asks if they could meet up some time.

Max: Ok, ok, um how about coffee? Do you like coffee?
Lorelai: Only with my oxygen.
Max: Can we drink some together? (Lorelai sighs) A sort of a pre-date – very casual, no strings, no obligations. We’ll just see if it’s even worth going down the road of including food in the deal (she shrugs, makes mischievous eyes) Just coffee? (sucks her breath through a smile) Decaf? Oh, there’s nothing safer than decaf (defeated huff).
Lorelai: I’m gonna be in town tomorrow because I take a class at Hartford State and there’s a coffee shop across the street that I sometimes – almost all the time – go to around 4:00, usually exactly 4:12. I could not stop a person from entering said establishment at around that time, nor would I avoid them if I knew them, if… they did.
s01e05 Cinnamon’s Wake

So Max had an uphill struggle ahead of him, not only having to support his apparent shunning of Rory’s efforts, but then finessing a date out of Lorelai. He laid the groundwork by leaving an answerphone message that let Lorelai know he was thinking of her and looked forward to their next meeting. Max has a few things on his side: he’s charming and confident and not unhandsome – although I have trouble figuring out what girls find attractive… I always thought Dawson was more handsome than Pacey, mostly because he had more chin but apparently not?

maaaaax medina

Mostly it’s Max’s confidence that gets him through the conversation, breaking down her arguments because he knows that really she’d like to spend time with him and vice versa. He’s got a good feel for the situation and isn’t afraid of being rejected. What’s the worst that could happen? He’s said he likes her and is just asking if she might like him back.  And is she sure?

Max: If there’s something in your gut that you know you feel is right, you’ve gotta go after it, no matter what. What do you say?

It’s a smooth sleight of hand on his part, both physical and verbal and Lorelai’s responses are worth a thousand words, but what we’re really looking at here is The Chase. The period that begins with realising you like someone and that they might like you and ending with one of you asking the other one out. This could go on for years (Luke) or a few days (Alex) and it can be nerve-wracking or sometimes more fun than the eventual relationship.

I’m looking at a few of Lorelai’s beaus here: Max, Alex, Jason and Luke – I don’t think we ever saw the girls having to do the chasing but correct me if I’m wrong… possibly Lorelai’s karaoke?

I think every argument we see between Sookie and Jackson is pre-dating. Maybe even counts as foreplay.

Alex, the coffee shop guy calls Lorelai at home after his friend accidentally asks her friend (Sookie) on a date. Under the guise of asking for some company with his testing different coffee shops for research on his own coffee shop…

Alex: So I was wondering what you were doing this Saturday.
Lorelai: You know, it’s funny you should ask me this, because I just happen to be one of the world’s foremost coffee experts.
Alex: Really?
Lorelai: Oh, yeah, it’s basically just me and this guy named Chuckles in Brazil.
Alex: Sounds like fate. So, what do you say?
Lorelai: Sure.
Alex: Great. Just to be on the safe side, you do know this is a date, right?
Lorelai: Oh, yeah, I got that.
s03e11 I Solemnly Swear

It’s a dazzling first date plan. It’s safe, because there’s something to do, something to talk about, in venues that they’ll actually be able to talk in and hear what the other person is saying. Not like the cinema where you a) have to sit side by side; b) not look at each other; and c) not talk to each other.  Coffee crawl – great plan, Alex.  Fishing as a second date, not so much.

Of course in Stars Hollow once a year you can always buy a date, by being highest bidder on someone’s picnic basket. With it being Stars Hollow, the dafter the rule, the more strictly it’s followed. It’s the perfect solution for Jess, the master of non-conversation, to spend time with Rory without it seeming like prostitution, which is basically what it is.

Jason ‘Digger’ Stiles is the master of The Chase. In their first meeting (which we recounted last week) Lorelai is only there to attack him for pulling the rug out from under her and her mother – and he still nearly wins a date out of it.


He returns a few episodes later and first talks himself into dinner, masterfully manipulating Emily’s social graces by threatening to go for a cheeseburger. Then under the cover of asking Emily for restaurant recommendations, he asks about cuisines and romantic places, all the while quite openly gauging Lorelai’s tastes. She’s impressed by his tenacity and interest and he’s in her head. He leaves answerphone messages and sends flowers, she finally calls back, refusing his date on the grounds that he’s in business with Richard her father and he’s from that world she has always tried to keep away from.

Jason: How’s the new inn?
Lorelai: Coming along, we’re gonna have horses
Jason: Talking horses?
Lorelai: No, just the regular ones.
s04e08 Die, Jerk

But he says he’ll keep his Saturday reservation at the sought after China Garden open, in case she changes her mind. At the annual Harvard / Yale football game, Richard’s annual lunches with Pennilyn Lott surface and Emily unreasonably blames Lorelai. Frustrated, hurt and knowing how mad it will make Emily, Lorelai calls Jason and finally takes him up on his offer.

With Luke, the pre-dating starts properly after the self-help tape where Luke Can See Her Face:

Self-help audio tape: Whose phone calls or visits are never unwanted or too long? Can you see her face? Who would you most like to have in your life, to ward off moments of loneliness? Do you see her face? When you travel, who would make your travels more enjoyable? Do you see her face? When you’re in pain, who would you most like to comfort you? Do you see her face? When something wonderful happens in your life – a promotion at work, a successful refinancing – who do you want to share the news with? Do you see her face? Whose face appears to you my friend? Whose face?
Luke: Whoa.
s04e20 Luke Can See Her Face

now that i've worn out the world

They slow dance at Liz and TJ’s renaissance wedding, to Sam Phillips’ lilting Reflecting Light and their pre-dating session comes to a close after eight years of banter, coffee and friendship culminating in this, on the porch of the newly renovated Dragonfly Inn:

Luke: Aw, I don’t want to calm down! I did everything right! I did exactly what the book said!
Lorelai: The book?!
Luke: I thought we were on track, and now you’re standing there looking at me like I’m crazy.
Lorelai: I’m not looking at you like you’re crazy!
Luke: You know the last time I bought flowers for someone? Never! That’s when! Very easy stat to remember!
Lorelai: I loved the flowers!
Luke: And then when I walked you home after the wedding, there was a moment. I thought there was a moment.
Lorelai: There was! There was a moment. [A beat. He leans into her.]
Lorelai: What are you doing?
Luke: Will you just stand still?
[He pulls her close, they kiss, then separate. Breathtaken, Lorelai moves toward him.]
Luke: What are you doing?
Lorelai: Will you just stand still?
[She takes his face in her hands and kisses him back. Another beat.]
Kirk: AAAaagGHHH! AAaaghHH! AAAaargGHHH!
s04e22 Raincoats and Recipes


The teaser quote was Kirk, who demonstrates as well as any of the other guys, that in the words of Thomas Jefferson, ‘”If you want something you’ve never had, you must be willing to do something you’ve never done.” Also, like Max and Jason (but not Luke), when he gets rebuffed, he gently questions it, but then accepts politely.

At the end of that episode, Lorelai also demonstrates a  gracious way to let someone down:

Kirk: You don’t need any other information?
Lorelai: No I don’t.
Kirk: Because I could have my mother call you.
Lorelai: Totally unneccessary.
Kirk: OK well then go ahead.
Lorelai: I just got out of a really weird relationship and I know that sounds like a line but it isn’t. I’m just not fully over the shock of it yet and I never want to hurt you because you’re my friend and I like you. So I have to say no. I’m sorry.
Kirk: Was the tuna inquiry too personal?
Lorelai: Oh no I thought it was very thoughtful.
Kirk: You’re sure you won’t feel like it any time soon?
Lorelai: Yeah, I’m sure.
Kirk: Well at least I asked. Good night Lorelai.
s03e02 Haunted Leg

Who was your favourite? Am I really the only person in the world who liked Jason best?

Pics c/o 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.

5 thoughts on “A Gilmore Girls’ Guide to Dating: Part Two – The Pre-Date

  • March 19, 2013 at 9:37 pm


    A nice two parter, surprised there haven’t been more comments.

    1- As to choice of preferred boyfriends: Luke>>Jason>Max>>Chris>>>>>>Alex
    2- As to chasing: Lorelai = Never really needed to, Rory = Sometimes [the insecurity of youth] like hoping sharing her article prep work with Logan will get her an invite to the dinner with the famous author
    3- As to the SH basket tradition: Seems like referring to it as prostitution is a bit of an overreach [at least as it referred to the girls] as there was never anything remotely approaching quid-pro-quo.

  • March 21, 2013 at 3:16 pm

    Well, after part 1 I am no longer able to be myself because I’m constantly wondering now if I’m really being myself or just a version of myself…thanks!
    It was always Luke, for me. And often I felt she didn’t deserve him, and she used him very badly, but even with everything I just still wanted them to get together, in the end. I wanted for her to stop being an idiot about Chris, and to stop running away with other guys, and just be really brave. If we overlook the ridiculous April nonsense Luke was so loyal, beautifully loyal. So kind. So caring. He understood her, he knew her, and he loved her anyway, inspite of her failings and perhaps even because of them. And he built her a freakin ice rink.

  • March 22, 2013 at 9:57 am

    Hi M ‘n Em, lovely to hear from you. I wonder if I didn’t have this as an outlet, how the Gilmoreisms would manifest. I’m envisaging a fair amount of twitching.

    I somehow forgot to mention Kirk filming his own pre-date for Lulu, where he’s ordered everything on the menu to assess sweater to crumb ratio.

    @Emma, don’t worry about it – just be yourself ;O) Luke knew what he didn’t want e.g. Rachel – but also what he did. I think part of him needed to be the saviour, for Jess, for Liz and for Lorelai. Even his chosen profession was providing sustenance – and being made use of was part of that. His reaction to April would have made more sense if she wasn’t already so fully formed and independent. I agree, he knew Lorelai and her quirks and loved the package. What did she see in him?

    Next week, actual dating – and hopefully something in the interim for Alexis’ engagement (squeee!!)

  • February 12, 2015 at 2:30 pm

    Hey, we never see the scene but Lorelai actually kissed Chris first… just because she wanted to know what it would like to kiss him. So she can do the ‘fishing’ too ;)

    • February 13, 2015 at 1:41 am

      There’s just too much love in the comments this week. I assume it’s to make up for all the lonely Valentine’s Days, so thank you very much. Big love y’all x


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