A Gilmore Girls Guide to Dating: What Makes a Good First Date?


A Gilmore Guide to Dating: The First Date

Good news first: In the Gilmore world, dating can be fun and inventive and you can enjoy the hell out of it. Especially if it’s snowing.

Lorelai’s official first date with Rory’s English teacher Max Medina is brought on by snow, Lorelai’s magical snow. His car chooses to break down in Stars Hollow while Rory is stranded at Richard and Emily’s, giving them a chance to get to know each other a little better, mooching around town and dicing with spicy Fiesta burgers which they take to the Black & White & Read movie night. They chat, smooch a little and he cajoles himself into the house, where unfortunately (for the grown-ups), Lane interrupts, waiting for Rory.

max coffee coffee

Dates are stressful on a number of levels. You’re with a stranger, often doing some activity to keep your mind off having to talk – when really the whole date is about getting more familiar and having to, y’know… talk. Lorelai and Max had a good time because they have a little banter, they’re a good match and it’s all the more charming because it was unexpected and natural. But Lorelai’s realistic about it:

Rory: Do you love him?
Lorelai: I uh… We had one date. It was a great date, World Series level… but it was just a date.
(s01e08 Love and War and Snow)

Lorelai’s first date with Jason ‘Digger’ Stiles is a good demonstration of the importance of finding the right activity. Do something you’re both comfortable with. A private room at a posh restaurant sounds nice, but isn’t fun enough for her tastes; the Taco Barn drive-thru is too exotic for him. Find common ground and if you’re confident enough, pare it right back, say, to plastic furniture outside a grocery store with a small can of Pringles and Sno Balls (ah, Sno Balls, you’ll be missed). The more quirky the activity, the better the stories you’ll be able to tell the grandkids (hey, I’m an optimist).

Likewise, Alex identifies a common interest, inviting her along for a coffee tasting recce. Less stressful than a formal dinner and very conducive for chatting, between sharing opinions on the brews, they’re people watching, getting a caffeine buzz and in all probability, mercilessly mocking the other clientele. Fishing as a second date though, not so hot.

If you’re courageous, make it personal. Take your date somewhere that means something special to you. Say, Sniffy’s Tavern with Luke and his wallet full of horoscope. As a couple, Luke and Lorelai had been building for a while before their official first date, so he was able to expose his sensitive side straight away:

[Luke tells the story of the first time they met, when Lorelai wrote over his horoscope and told him to hold onto it, to keep it in his wallet. That it would bring him luck.]
Lorelai: Uhm I can’t believe you kept this.. You kept this in your wallet? You kept this in your wallet.
Luke: Eight years.
Lorelai: Eight years.
Luke: Lorelai. This thing we’re doing here, me – you. I just want you to know I’m in. I am all in. Does that uh – are you… scared?
[Lorelai shies away, then glances up at him, smiling. She doesn’t look scared.]
(s05e03 Written In The Stars)

There’s some anti-April sentiment (Luke’s daughter he never knew he had, not the month) on the discussion boards, which I think is largely a reaction to this moment. When things between Luke and Lorelai become muddy and Luke becomes confused about his paternal priorities, he effectively takes back the touching moment at Sniffy’s. But it’s not April’s fault.

Rory has her fair share of first dates too, especially after she starts college. Although it’s not all good:

Rory: I feel like I was locked in to a pointless societal ritual. There has to be another way.
Lorelai: Luke and I were debating that. Luke thinks it’s all about gut instinct. You know instantly if a person’s right for you. I think you have to go through a lot to find a contender. You’ve been very lucky with boys before, they were just sort of there. But, I think for the most part a girl’s gotta hunt a little.
Rory: And go through a lot of non-contenders.
Lorelai: Yes but then your non-contenders become your fun bad date anecdotes.
(s04e05 The Fundamental Things Apply)

Which leads me onto… Bad Dates in the Gilmore Girls (A Necessary Evil)

Halfway through a disastrous first date at Yale, Rory calls home for advice while Clark-Kent-a-like Trevor is in the bathroom. Luke’s there too, Lorelai’s captive Casablanca guinea pig:

Rory: I’ve already forgotten everything he said to me, the name of his brother and sister and best friend and we’re sitting on the same side of the table, we keep bumping menus and my neck already hurts from trying to turn and look at him when he talks. Can I tell him to sit on the other side?
Lorelai: Honey, you just have to relax. ‘Cos it’s just a date and sometimes dates don’t go well.
Luke: Dating’s the worst.
Lorelai: Don’t worry about the conversation. Just talk and if the talk doesn’t flow, it doesn’t. And stay away from urine-related topics.

But Lorelai has the experience to know that bad dates can have good sides. And she should know…


Sookie and Jackson are on their first date, Lorelai is helping out by double-dating Jackson’s flat-cap-toting cousin, Rune – an unintentionally funny little man, disgusted by Lorelai’s height and size 9 feet. They leave the stuffy French restaurant in favour of Luke’s and after Jackson and Sookie start to relax and get rid of Rune (“Bye Loon!”), they can properly talk – leaving Lorelai and Luke to play a little poker over the counter where Luke first raises the suggestion of Lorelai going out sometime.

Lorelai: God that’s nice. The whole first date beginning of the relationship glow, everything’s new and exciting.
Luke: Every joke is hilarious.
Lorelai: Every little touch is incredible. That is a good feeling.
Luke: It is at that.
(s01e12 Double Date)

In the same episode, Rory and Dean are double-dating for Lane Kim and airhead Todd, which comes to a head when ultra-strict Mrs Kim finds out. The confession by Rory about how she lied to Lorelai to prevent Lorelai having to lie to Mrs Kim throws out one of my favourite lines:

Lorelai: I have to know where you are at all times, especially when you have my shoes on.

Some final pearls from Luke and Lorelai:

Luke: I mean dating, it’s a horror.
Lorelai: It’s the only cure for the singleness thing barring ordering a spouse off the internet.

Lorelai: But dating is how you get to know your potential partner. It’s the only way.
Luke: There’s the gut. I can tell if I’m comfortable with someone within seconds of meeting them.

Which camp are you in, Luke or Lorelai’s? Ever had Luke’s gut feeling? Or is dating the only way?
What’s your worst date ever?
Which is your favourite Gilmore first date?

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.

4 thoughts on “A Gilmore Girls Guide to Dating: What Makes a Good First Date?

  • May 20, 2014 at 11:12 am

    I’m just a few posts shy of 100 posts and reminiscing. This was the the only blog that never got a comment. I’m rectifying that while simultaneously winning the Stars Hollow 2015 Cosplay competition by choosing to go as Snow-Bjork :OP

    I would have liked to have seen more of Jess and Rory’s dates.

  • May 20, 2014 at 11:20 pm

    Yes, I would have liked to as well. I felt that they went very fast from Rory/Dean with Jess as onlooker to Jess leaving town with only a few bits in between those stage. Particularly compared with a much larger number of more standard dates for Rory/Dean and Rory/Logan (perhaps because, as IMDB tells me, Jess was in only about half the number of episodes of the other two – 37 compared to 63 and 59). There is the bit in season 3 somewhere where they’re talking films and takeaway in front of Lane, but I don’t think we ever saw any of their film and takeaway evenings.

    • May 21, 2014 at 11:32 am

      It was cool when they shared a takeaway with Paris that time at Rory’s house. And when Kirk was there at breakfast but that doesn’t really count as a date :0)

  • May 21, 2014 at 8:26 pm

    Hi Rich-

    Congrats on hitting triple digits. Have enjoyed being a part time wing-man on the journey. As to the Cosplay question, since I travel so little these days, I will probably have to settle for being the ever-absent Mr. Kim–


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