Lorelai Gilmore has a reputation for being fun, funny, and smart, and this Gilmore Girls character's parenting approach is highly praised by countless fans. People connect with Lorelai because she makes life entertaining and enjoyable, always indulging at Luke's Diner and planning movie nights with lots of junk food.

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But while fans know that Lorelai loves Rory and wants nothing but the best for her, sometimes Lorelai's actions suggest that she could be more careful and intentional with her parenting. There are some moments on Gilmore Girls when Lorelai should help Rory more instead of trying to seem so cool all the time.

When Rory Is Unsure About Chilton

Lorelai talking to Rory reading a book on Gilmore Girls

When looking at Rory and Dean's relationship in every Gilmore Girls season, it's clear that season 1 features the most dramatic moments. This includes Rory meeting Dean and getting nervous about leaving Stars Hollow High for Chilton.

Lorelai and Rory get into a big argument because Lorelai says Rory is going to throw her life and future away for a love interest. But it would make more sense if Lorelai would calmly and rationally listen to Rory's thoughts and feelings. Lorelai approaches this situation with emotion instead of logic, and if she was a better parent, she would understand that Rory feels like Chilton is a huge and terrifying step.

When Rory Steals The Boat

Logan and Rory about to steal a yacht on Gilmore Girls

Rory's pain and confusion over Mitchum's negative view of her work ethic leads her to steal a yacht at the end of season 5. Lorelai is understandably angry when Rory drops out of Yale and wants to live with her grandparents.

But instead of continuing to give Rory life advice and lend her support, Lorelai gets so mad that she tells Rory, Emily, and Richard that they can figure out this problem themselves. Lorelai needs to be more involved in her daughter's life instead of walking away and indulging in her hurt feelings. Maybe Lorelai and Rory could have worked out a plan to move forward.

When Lorelai Interferes In Rory's Love Life

Jess, Rory, Lorelai, and Luke eat at Luke's diner on Gilmore Girls

Out of Rory's three major love interests, Lorelai seems to like and prefer Dean. She thinks that Jess and Logan are irresponsible and that they don't have the same work ethic as Rory so she shouldn't date them. Lorelai gets too involved, though, and even plans Rory and Dean's first date by inviting him over for movie night.

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Lorelai is being unfair, as both Jess and Logan genuinely care about Rory, and there's really nothing to be so concerned about. Lorelai needs to be a stronger parent and let Rory make her own dating decisions without judging her partners so harshly. Rory is still young and she knows that she can lean on Lorelai if she needs to.

When Lorelai Wants To Date Max

Lorelai and Max in Max's kitchen in Gilmore Girls

Many Gilmore Girls fans debate Lorelai and Max's relationship and disagree with Lorelai's decision to date her daughter's English teacher. This romance doesn't get off to a very positive start, as Lorelai wonders about dating Max out in the open, and she struggles with telling Rory.

This is definitely a time when Lorelai should remember that she's a parent and this isn't the smartest relationship to get involved in. Lorelai's decision has a terrible ripple effect on Rory, who feels uncomfortable and has to deal with the whole school finding out. Lorelai should be focused on helping Rory succeed at Chilton.

When Lorelai Is Disorganized On Rory's First Day Of School

Split image of Lorelai coming down stairs and Lorelai and Rory at Chilton on GIlmore Girls

In the season 1 Gilmore Girls episode "The Lorelais' First Day At Chilton," Lorelai doesn't have clean clothes to wear to meet the headmaster of Rory's new private school. Lorelai explains that her suit is at the dry cleaners' and since it's laundry day, she has no other options.

This isn't a great example of Lorelai's parenting, as she's so disorganized and chaotic that it stresses Rory out and only upsets Headmaster Charleston, who wonders about Lorelai's commitment to Rory's success. Lorelai should have put out three potential outfits a full week before Rory's first day, and then none of this would have happened. Fans feel bad that Lorelai is so embarrassed, but this whole mess could have been avoided.

When Lorelai Elopes With Christopher

Christopher looking at Lorelai who looks upset on Gilmore Girls

Lorelai shocks fans by eloping with Christopher in the season 7 episode "French Twist." Most viewers don't think that Christopher is the right person for Lorelai, and more than that, this is one of Lorelai's poorest parenting moments.

Rory is upset that her parents wouldn't want her to be at the wedding and rightly so. This seems like something that Lorelai should have thought about beforehand. While Lorelai has a fun, sometimes impulsive personality, she's used to being a parent first, and that should carry some weight here.

When Lorelai Doesn't Encourage Rory To Get Involved At Chilton

Split image of Rory Gilmore reading on Gilmore Girls

In the season 2 episode "Like Mother, Like Daughter," Headmaster Charleston doesn't understand why Lorelai hasn't joined the parents' group at the school. He's also upset that Rory has neglected to join any extra-curricular clubs or groups.

RELATED: Rory's Most Wholesome Moments At Yale & Chilton On Gilmore Girls

This episode has a funny storyline as the Puffs, an elite Chilton secret society, recruits Paris and Rory. But it's also a reminder that at times, Lorelai wants to be Rory's best friend so bad that she doesn't remember that she's her parent. From the beginning, Lorelai should tell her daughter that she needs to join at least one club and try to make some new friends.

When Rory Is Lost In A Year In The Life

Rory sitting at her desk in the Gilmore Girls revival

It's heartbreaking for fans to see Rory's journey in the Netflix revival A Year In The Life. Based on the fact that she succeeds at Chilton, writes for Chilton and Yale's newspapers, and writes about Obama's presidential campaign, it seems like she's ready for a fabulous writing career. Instead, the book Rory is writing falls apart, she can't get pitches approved, and she doesn't have a regular job or freelance career.

Rory and Lorelai share many sweet and funny moments in the revival that bring back nostalgic feelings for the original series. But a serious discussion is definitely missing in action here, as Lorelai should be more concerned about Rory's future than she seems to be.

When Lorelai Takes Rory On A Road Trip

Rory and Lorelai are in a truck driving in Gilmore Girls.

The season 2 Gilmore Girls episode "The Road Trip To Harvard" has one entertaining moment after another, as the mother/daughter duo stay at a hilarious B&B and are in awe of seeing Harvard in person. But when viewers think about it, this is a time when Lorelai isn't much of a parent.

Parenting involves a lot of careful thought, planning, and responsibility, and Lorelai could take Michel, Sookie, or even a neighbor like Babette on this road trip. She and Rory could see Harvard during Rory's summer break from school, and Rory's life wouldn't be disrupted. It's tricky enough that Lorelai has canceled her wedding to Max, which has to be confusing for Rory, who must be nervous about having a stepparent.

Lorelai Fights With Rory For Suggesting She Borrow Money From Emily And Richard

Lorelai and an upset Rory at the Stars Hollow summer festival on Gilmore Girls

The season 2 episode "Secrets And Loans" sees Lorelai in an awkward position as her house has a termite problem. Rory wants Lorelai to ask Emily and Richard for money, and Lorelai thinks it's a horrible idea.

It's tough that Lorelai would rather fight with Rory here than admit that this is the best and most practical solution. Lorelai often wants Rory to think that she's cool and this changes her behavior during some important moments. Lorelai should think about how her daughter needs to live in a house with any major issues and go ahead and ask her parents this hard question.

NEXT: Rory & Lorelai's Relationship Timeline On Gilmore Girls, Season By Season