Lorelai Gilmore is the heartbeat and funny bone of Gilmore Girls, mostly because she works so hard to give her daughter the best life possible. Rory and her mom have a special relationship that is marked by specific life circumstances and choices. Lorelai tries to think through each decision carefully, and she gets it right sometimes.
However, there are numerous occasions where Lorelai misses her mark despite her best efforts. She's only human, and her good intentions are known to have unexpected outcomes sometimes.
Movie Night With Dean
One of Lorelai's most famous awkward mom moments is when she invites Dean over for pizza and a movie without asking Rory first. Gilmore movie nights are a sacred ritual for the mom and daughter, but Lorelai wants to adapt a movie night so that both she and Rory can get to know Dean better. Lorelai might be known as a cool mom, but she still likes to keep an eye on Rory's suitors. She's trying to make the night fun for Rory and Dean, even though the situation could be perceived as entirely uncomfortable.
Although Rory and Dean have a pretty good time, it's weird that Lorelai tries to have a talk with Dean alone, setting a precedent for other weird encounters she has with him later on.
Chilton Parents' Day
Lorelai is noticed at Chilton throughout Gilmore Girls, and not always in a good way. Aside from her infamous "laundry day" outfit on Rory's first day, the first year at Chilton includes some other surprises. One occurs when Lorelai attends Parents' Day at the school. She is taking the time to try to be a good mom and be invested in Rory's education, but her feelings get the best of her.
Lorelai is in a relationship with Rory's teacher, Max Medina, at the time. She stays after his literature class to try to break up with him, which is the right thing to do because of the position their relationship has put Rory in. However, Lorelai and Max argue and end up kissing. The worst part? Paris sees them, so Rory hears about the kiss from her.
Financing The Termite Exterminators
Lorelai and Rory aren't made of money, so Lorelai tries to be frugal about their spending (despite all that eating out). When she has termites at the house, the cost is staggering and is more than Lorelai can afford. She tries everything to come up with the money without asking her parents for it. Rory isn't interested in abiding by her mom's wishes, so she tells her grandparents about the problem.
Lorelai is stubborn and doesn't want to accept the money from them, but her best efforts at paying for the expense turn into even more of a headache. Finally, Lorelai and her mother go to a bank together, and Emily gets Lorelai to accept the help in financing the necessity.
Hiring Jess Turns Tense
When Jess becomes a part of Luke's life, Luke wants to give Jess a chance to be part of the community and make something of himself. Lorelai attempts to put her weird feelings about Jess aside a couple of times, like when she lets Rory tutor him, and when she hires Jess to do some yard work.
The latter example is disastrous. Lorelai is earnestly trying to give Jess an honest job, but the mom catches him coming out of Rory's room and overreacts about the Dean bracelet debacle. Jess pocketed Rory's special Dean bracelet when Rory dropped it during the town picnic event, and Rory doesn't even notice it's missing until Dean says something. What should have been a simple day of yard work turns into a tense encounter between Lorelai and Jess.
Paying Emily & Richard Back
Lorelai seems unable to escape a financial connection with her parents. In the third season, Richard surprises Lorelai by giving her $75,000, a sum which he invested in her name when she was born. Lorelai and her dad have a pleasant conversation about this, but things go south when she decides to use the investment money to return a favor. Lorelai is making a kind decision in wanting to return the money to her parents to pay them back for Chilton.
However, the gesture does not translate well, especially for Emily. After all, the Chilton arrangement is how Emily and Richard found their way back into Rory and Lorelai's lives. Ending that could easily feel like a closed door.
Grown-Up Milk & Cookies
Lorelai can't get over her past with Christopher on Gilmore Girls, either. After Christopher's father es away, Rory and Lorelai both extend their condolences. Rory brings her dad milk and cookies, and Lorelai shows up immediately after with tequila, or as she calls it, "grown-up milk and cookies."
The visit is innocent enough, but Lorelai feels funny about it and hides it from Luke, who finds out at Emily and Richard's vow renewal. Luke doesn't like other people keeping secrets from him, so Lorelai deals with the consequences of trying not to upset him in the first place.
Lorelai Telling Rory To Go Back To Yale
The worst fight of Gilmore Girls is the big one between Rory and Lorelai. When Lorelai decides to take a leave of absence from Yale, her mother is not happy with this decision. Lorelai wants the best for Rory, especially since the mom's path did not originally include a college education.
Rory does not appreciate her mother's opinions, so the Yale disagreement causes a huge rift in the relationship.
Catering With Sookie
Catering turns out to be a viable skill for Sookie, who is already a gifted (though haphazard) chef. Perhaps this venture would have been better for Sookie to enter alone. Lorelai tries to make the most of an opportunity with her friend when the two agree to cater a child's birthday party.
Unfortunately, the event is almost a wash when Sookie sticks with foods fit for an adult event, and Lorelai is stuck running out to salvage the party for the kids. This isn't the only time that Lorelai's good intentions in business with Sookie backfire.
April's Sleepover
One of the oddest challenges Luke and Lorelai face centers around April Nardini. The young woman is excited to get to know Luke as a dad, but her mother doesn't want April to cross paths with Lorelai. When Luke asks for Lorelai's help at April's sleepover, she is there for him. Lorelai is good with kids and is willing to help turn the party around, but her decision doesn't bode well for herself or for Luke.
Anna Nardini isn't willing to bend her rules due to the fact that she doesn't want anyone to come into April's life and then leave. Lorelai threw a great party, but it didn't help her situation with Luke or April at all.
The Character Reference
Another huge Luke struggle is the character reference he asks Lorelai to write in the final season. Obviously, Lorelai has plenty of positive things to say about Luke. She's married to Christopher at the time, though, and he can't stand Lorelai having anything to do with Luke.
For that reason, Lorelai hides the character reference letter. Christopher finds it and permanently walks out. Some fans might be excited about this, but it wasn't the outcome Lorelai had hoped for.