Dear Emily And Richard originally aired February 4, 2003. This episode was written by Amy Sherman-Palladino and was directed by Gail Mancuso.

This episode starts off another Friday night dinner, where Richard and Emily are horrified that Rory and Lorelei plan on backpacking through Europe and staying in hostels, instead of staying in hotels for their trip to Europe.
From there, we see a bit of the construction on the soda shop, and we learn that Dean is helping Taylor out. There is also going to be a retirement party at the inn, which has an ever-changing theme.
We go to a flashback, where Lorelei and Chris are at Emily’s and Chris is talking about how he wants to take a year off and travel around Europe for a year instead of going to college.
Rory is at Chilton, working on the paper, when she gets a call from Sherry’s friend Maureen. Sherry, of course, has screwed up by going into labor early, instead of sticking to the c-section that she had scheduled for the following week. Maureen wants to know if Rory can reschedule school and go to Boston, since Sherry screwed up, but Rory says she’ll be there.
We have another flashback, where Lorelei can’t fit into her dress for the portrait she’s having done for her coming out.
Back in present time, Lorelei meets Nicole at Luke’s because she needs some coffee before heading over to Emily’s.
Rory arrives at the hospital to see that only Maureen is there, because everyone had planned on next week’s c-section, because yet again, Sherry has screwed up. Maureen goes back to work, while Rory goes to see Sherry, who is feeling abandoned. Sherry is not happy about having GiGi at the moment, because she wrote it down for next week, and that it’s not supposed to be happening.
Lorelei goes to see Emily on…a Sunday. Richard is out of town again, and Lorelei is curious about what Emily does all day while Richard is gone. Emily spends her time on functions and fundraising events and the DAR and managing the household. Emily doesn’t watch a lot of tv, but does like musicals.
We have another flashback, where Richard and Emily and Chris’ parents are talking about what to do about Lorelei being pregnant. Francie wants to send Lorelei away, because there are places for girls like her. Strobe suggests abortion, and Richard suggests that Chris and Lorelei get married, live with Richard and Emily, and Chris will go to school and get a job at Richard’s firm. It also comes up that Chris shouldn’t sacrifice everything because Lorelei got pregnant. Richard goes to his study, and we see that Lorelei and Chris are listening on the stairs. Lorelei thinks they should decide for themselves what to do, but Richard’s plan sounds fine to Chris.
Back in the present, Rory is helping Sherry with work stuff, and we learn that Chris is out-of-town but is also on his way. A nurse wants to know who’s going in with Sherry, and it’s going to be Chris. The nurse wants to know who will go in with her if he’s not there, but Sherry wants to wait until he’s there. The nurse isn’t accepting this, and it’s decided Rory will be with Sherry in the delivery room. Rory decides that she needs a coffee break, and goes out of the room to call Lorelei, because Rory really needs Lorelei there. Of course, Lorelei goes, which doesn’t go over well with Emily, who still thinks that Sherry destroyed any chance of Chris and Lorelei being together. And Emily also doesn’t understand why Rory is there or why Lorelei is going.
Lorelei arrives at the hospital, where she manages to get Sherry to stop working. Chris also arrives just as Sherry is going into the delivery room, much to the relief of Lorelei, who does not have to be with Sherry in the delivery room.
We also have a few more flashbacks. One where Lorelei arrives at the hospital, one where Richard and Emily arrive at the hospital after getting Lorelei’s note, and one where Chris and Lorelei are watching Rory in the nursery.
Chris comes out of the delivery room, and Lorelei goes to see GiGi, since Rory is sleping. He eventually goes to get Rory, and we next find Lorelei at Emily’s to set up a DVD player, so that Emily can watch musicals.
We have one last flashback where Emily and Richard are going to a function, and discover that Lorelei has left because of a note she left for them.
The episode ends with the viewer looking at a portrait of Richard, Emily and Lorelei.
My Thoughts:
Let’s start with Emily’s reaction to Sherry’s pregnancy. She’s still clearly not happy about it, and it is important to point out that Lorelei went to Boston because Rory called her. And of course Rory is going to be there, because GiGi is her half-sister.
Maureen going on and on about how Sherry screwed up by going into labor early…I was really annoyed with that! I honestly don’t know why she keeps focusing on that. Because when it happens, it happens, and there’s no stopping it. And Sherry not wanting to do it because she wrote it down for next week…I’m sure scheduling a c-section is a thing that actually happens with a certain segment of the population, but the way Sherry and her friends are acting…it just seems like they’re a bit out of touch with how being pregnant goes for most women.
Also, what day is this happening? Because it’s said that it’s a Sunday, which means the Chilton newspaper staff is at school on a Sunday. Since it’s been a while: what kind of school is Chilton that it lets its students be there on a Sunday to work on the paper? It being on a Sunday doesn’t match up with Rory rescheduling school. Again, Maureen seems to be slightly out of touch with the fact that school is mandatory and can’t be rescheduled. Although…it can’t be regular school hours, since Rory just leaves, unless it’s something that happens off-screen.
I really want to focus on the flashbacks, which were totally amazing. They worked with this episode really well, and they were so seamless! I feel like this is the most neutral version of Lorelei’s pregnancy that we get in the entire series. I don’t think I picked up on this before, but Lorelei and Rory’s trip to Europe when Rory graduates…I wonder if it’s inspired by the trip that Chris and Lorelei never took? It is like Lorelei to not tell Richard and Emily she’s in labor, and I actually don’t blame Emily for being upset that Lorelei just left a note. As for the conversation all of the parents have, I’m not surprised that Francie suggests Lorelei be sent away, that Strobe suggests abortion, and that Richard suggests marriage. I am curious as to why adoption doesn’t come up, but then again, adoption rarely seems to come up in these situations.
Them living with Richard and Emily make the most sense, given how Francie and Strobe react. I know homes for pregnant teens was a thing at one point, but was it still a thing in the 80’s? Because I wasn’t alive for half the 80’s, and I was too little to remember the other half, so I have no clue.
And the flashback where Emily discovers that Lorelei has left home? I kind of get some of the tension between Emily and Lorelei, and if Lorelei just left with a note…I feel like I have a better understanding of where Emily is coming from.
Pop Culture:
I know they’re there, I just didn’t keep track of any of them.
Favorite Funny Moment:
Everyone’s reaction to the retirement party changing themes.
Episode Rating:
This is the only episode where we have flashbacks, and if there is any episode that warrants them, it would be this episode. This is one of the best episodes of the series, and some of the tension between Richard and Emily and Lorelei make more sense. Dear Emily and Richard gets 5 mugs of coffee.
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