A Gilmore Girls’ Guide to Dating – Breaking Up


More relationship lessons, as taught by those delightful Gilmore Girls.


Lesson 1: It’s OK to break down and snot up the bed.  In fact, it’s healthy.

Lorelai: Oh yeah, get back in your pyjamas, go to bed, eat nothing but gallons of ice cream and tons of pizza, don’t take a shower or shave your legs or put on any kind of make up at all and just sit in the dark and watch a really sad movie and have a good long cry and just wallow. You need to wallow.
s01e17 The Breakup, Part 2

Witness the same after Lorelai’s break-up with Luke, where she confines herself to solitary bedrest, ended only an ill-advised Streisand-induced answerphone message to Luke and the immediate need to sneak out and steal the same.

Lesson 2: It’s OK to run away.  Distractions can be helpful.

Escaping her broken engagement with Max, Lorelai takes Rory and the Jeep on an impromptu road trip, encountering a cat-infested guest house and the Harvard campus.  Both girls re-focus their direction, Lorelai to what she wants from her inn and Rory to college.

Lesson 3: To Box or Not To Box?

After Rory’s catastrophic response to her first ‘I love you’, she boxes up everything Dean gave her, everything he ever touched, including books, clothes and the innocent Colonel Clucker.

Rory: No, take it out of the house. Throw it in a dumpster, burn it, I don’t care. Just…I want it gone.
Lorelai: You know, honey… Some day, when all of this is in the past, you may be sorry that you don’t have some of these things anymore.

Instead, Lorelai hides the box in the cupboard, alongside her own box containing stuff from Max.  Which turns out to be the right thing to do since Lorelai is able to later return Max’s book and Rory ends up back with Dean.  For a while.

Lesson 4: There’s a right (and a wrong) way to end it.

Ah, Jess.  Rory and Jess show us two, or maybe three good ways to end things, which end up colouring the way they pick it up the next time.  Their first attempt at friendship ends when Jess crashes her car and flees to New York.  He still calls, she goes to find him, gets a sense of closure and moves on.

Second time, unable to let go, he comes back and they officially start dating but he fails Rory by failing school and unable to buy tickets to homecoming, runs away to find his dad in California.  This time he calls but can’t bring himself to talk and she ends it – not madly, not unkindly – thus:

Rory (on the phone to a non-responding Jess): I think… I think I may have loved you, but I just need to let it go. So, that’s it, I guess. Um, I hope you’re good. I want you to be good, and, um, okay, so, goodbye. That word sounds really lame and stupid right now, but there it is. Goodbye.
[Rory hangs up. Jess hangs up the payphone and walks away down the boardwalk]
s03e22 Those Are Strings, Pinocchio

After a few years of not hearing from her, he shows up again as a small success – although Logan’s on the scene and Rory has to come to terms with what she really wants from life, as well as love.  With time and distance, Rory and Jess can now give each other what you’d want from a friend: encouragement, support and love.

Jess: You know what I mean. I know you better than anyone. This isn’t you.
Rory: I don’t know.
Jess: What are you doing? Living at your grandparents’ place, being in the DAR, no Yale…why did you drop out of Yale?!
Rory: It’s complicated.
Jess: It’s not! It’s not complicated.
s06e08 Let Me Hear Your Balalaikas Ringing Out

Conversely, Logan’s departure after the public embarrassment of his declined marriage proposal leaves a stink behind, but isn’t that what you’d expect from a Huntzberger?

Rory: But we could at least try?
Logan [shrugs]: What’s the point?
Rory: … so…
Logan: … so… [Rory takes the engagement ring and he begrudgingly takes it back]  Goodbye, Rory.
s07e21 Unto The Breach

But then talk about keeping distracted – she lands a job in the news corps following pre-Presidential Obama.  But where do you think her head goes when she’s lonely in her hotel room each night?

Lesson 5: Staying friends.  

Rory and Jess did it, after a peaceful ending and helped with distance.  Lorelai’s tactic with Luke is more head-on, taking him car shopping.  Lorelai is so particular and Luke so frustrated with her that he vents his honest feelings, clears the air and feels so guilty about it that he gets her what she wants.  Because they do still love each other, they just maybe aren’t in love with each other right now.  It’s do-able, because they’re being open and honest.

Lesson 6: Not breaking up.

It’s an option!  After all, who’d have thought Paris could be talked out of dumping a guy, by the guy?

Paris: What are you talking about?
Doyle: I love you, Paris Geller. You are the strongest, most infuriating, most exciting woman I have ever met in my entire life, and there is no way I’m gonna let you go.
s07e19 It’s Just Like Riding A Bike

But then, as Rory points out, ‘… Doyle’s not just some guy.’

So, tell me…

Ecclesiastes (and Footloose) assure us that there is a time for every purpose under heaven.  A time to laugh, a time to weep. A time to mourn and a time to dance.  Do you agree that there’s a time to wallow?
Do you think Jess was qualified to comment on Rory being with Logan?
Box or no box?
Will Rory and Logan ever see each other again?



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.

6 thoughts on “A Gilmore Girls’ Guide to Dating – Breaking Up

  • September 11, 2013 at 9:35 am

    Jess and Rory:
    To me, the interesting ending to this was the one later in season 6. Where he wants her back and she tells him she loves Logan. I felt that Jess showed the full maturity then by accepting that they felt differently (something like “it is what it is”). Also, I felt that things weren’t quite closed as Rory needed to come full-circle by treating him better in some future meeting. Although whether it would be romantic or friendship depends on where Amy was going with this. I was never quite sure.

    Logan and Rory:
    Bad ending, but he was supposed to be back in season eight. Maybe he was supposed to be her ultimate match coming from the world her mother left and bringing that full circle, or maybe he was supposed to be the relationship that she eventually saw as too far from her Stars Hollow upbringing. As for Jess, I don’t know about Logan as it depends who Amy intended Rory to end with, if she was supposed to end with someone specific.

    Finally, I was never convinced that Dean’s exit counted as closure (what, with the resentment), although it did feel played out. I don’t think there were ever plans for him to return.

    I felt that the long game was aimed in Jess’ favour – if anyone’s – but it’s a very close call between him and Logan.

  • September 12, 2013 at 7:50 pm

    Hi Rich-

    Interesting topic.

    As to breakups, there is no right way to do it, only less severe degrees of wrong that let the healing begin sooner. And of course the POV [breaker vs breakee] will significantly tint the interpretation of how right or wrong the event truly was. Breakups tend to be seminal events in people’s lives that can have after effects for years, mainly because they pinpoint flaws in our characters that we were not aware even existed [or at least wish didn’t exist]. And that occurs because we never want to have to admit to ourselves that our judgement was flawed in taking a friendship to the next level only to find out we misread that person or that we could ever behave so badly once this error becomes apparent and we part ways with that person.

    As to the particulars of Gilmore Girls, from the Girl’s understandable wallow time [as the breakee], to Lorelai’s self-centered cowardice with Max or Jess’s frustrated cowardice with Rory [as the breaker], to Luke’s physically acting out against an inanimate object upon losing Nichole, Lorelia’s exasperated shouting match with Jason at the Inn, Rory’s passive-aggressive “what do you expect from me” reactions to both Jess’s disappearance and later Logan’s proposal from out of the blue, we see a variety of ways that breakups can occur [reminds me of the old Paul Simon song].

    Some of the recovery dynamics make sense [particularly sad or mad to blow out some of the cobwebs], but running so far up d’Nile that you can hear Victoria Falls seems extremely counterproductive. [Always thought the writers let Lorelai off the hook way to easily for the way she treated Max.] Then in addition to still owing the other person a currently unspoken explanation/apology you also have to look at yourself each day and be disappointed in your own behavior. No amount of distraction changes that fact and it influences how you go about building future relationships.

    As to the other lessons or questions:

    1] TB or not TB? Immaterial over the long-term as the memories will always remain. Over the short-term maybe not TB to escape the reminders of what’s missing.

    2] While Jess believes he has something to gain by pointing out Rory’s bottoming out with Logan [so his reaction is not just friendship], the fact remains that he was the only other person who was close enough to her in that way that she might actually listen.

    3] Rory on the campaign trail and how she regained her groove – Wallow initially on the loss of love but quickly develop friendships with like minded people on the bus [Think Holly Hunter and Albert Brooks from Broadcast News].

    4] The resolution of the Rory-Jess–Logan Triangle? Logan moves on to the next BBD but is smart enough not to entirely break the bridge as he and Rory may find their paths crossing later in their narrow field of specialization. Jess always would remain a friend hoping for more but not really expecting/counting on it [though always ready to pounce if the opportunity ever materializes]. Rory of course is every bit as independent as Lorelai and smart enough to realize there are more than two guys in the world worth considering. That fact probably is the biggest disappointment if a recap movie ever occurs since by definition you lose half the audience when you make a final decision in Rory’s personal life between Logan and Jess and if you pick an entirely new guy the audience would downright revolt!!

  • September 25, 2013 at 8:51 am

    Oh my goodness, imagine the uproar if Rory’s new guy won!

    The box thing stays with me, since immediately after, it makes sense to get rid of everything. But later on, you might want to hold onto something real, as a keepsake. What you really want is a Lorelai, to help you have both.

    “It’s all any of us wants, to find a nice person to hang out with ’til we drop dead. Not a lot to ask.”
    ~~ Lorelai

  • October 3, 2013 at 10:46 am

    No box. Unless you’re 16. Any older and that’s just a bit pathetic. Also, if you forget you’ve got the box and then later on your future partner finds it, it can lead to some awkward conversations…

    I won’t have it that Rory ended up with anyone other than Jess. There are no other guys :)

    • October 4, 2013 at 7:56 am

      Sounds like you’re speaking with the wisdom of hindsight. Do tell! Was it a six year old box of corn starch kept in the bedroom?

  • October 7, 2013 at 2:55 am

    @Lathany… while watching the final series was like watching a ‘best of’ for the rest of the show, it’s a relief they didn’t bring back Dean in the last series for beating that dead horse. It did feel like there was sufficient history between them to count as closure – or at least enough of a mess for everyone to not go back to.

    I’m wondering, if he was introduced in the right way and was somehow a better fit, whether there would be a viable new boyfriend for Rory. He has Jess’ bad boy past, Logan’s charm and Dean’s car-building skills. Let’s call him Rich and he secretly writes a Gilmore Girls blog. That’d work, right?


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