The 10 Worst First Dates The Characters Ever Had

Not everyone can have a magical first date like the one that Luke and Lorelai, or even Kirk and Lulu, have on Gilmore Girls. There are countless couples that fans dislike throughout the show’s seven seasons. Then, there are others who just have bad dates.

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A first date is a tricky thing, and Gilmore Girls expresses this perfectly. From nights that start off nervously to inescapable awkward conversations, plenty of characters in the series go on lackluster first dates. These are the worst ones, in increasing order of terribleness.

10 Lorelai & Max

There’s nothing quite like a first date that won’t take off. Fans love it when Lorelai is with Max Medina, even though he is Rory’s teacher. Max and Lorelai keep bumping into each other until Lorelai agrees to go on a date with Max. It turns out that the date is scheduled for the same night as Cinnamon’s wake.

Lorelai chooses Babette’s deceased cat over Max, ruining the evening before it can even begin. Luckily, Max gives her another chance, but she blows that, too.

9 Rory & Dean

Even when a boyfriend does the sweetest things, dating can still be awkward, especially a first date. Fans on Team Dean go crazy for the first date Dean and Rory share, but it’s not that great. There is a weird type of energy when Rory, Lorelai, and Dean are in a room together, and that is evident when Dean goes to Rory’s for movie night.

Maybe Rory felt more comfortable having her mom there, but it doesn’t give Rory and Dean much space to get to know each other better.

8 Paris & Jamie

Paris Gellar Dating Meme

Viewers don’t get the pleasure of seeing Paris’s entire first date with Jamie, but it isn’t set up too well. Her nerves are at an all-time high, and she can’t stop worrying about the evening. Her feelings are relatable, though.

Paris asks Rory, “I’m covered in hives, I’ve showered four times, and for what? Some guy who doesn’t even have the brains to buy a Zagat so we don’t wind up in a restaurant that’s really just a front for a cocaine laundering ring?” This isn’t looking good, and Jamie doesn’t work out in the end, anyway.

7 Emily & Simon

Emily Gilmore with Simon McLane

Emily and Richard Gilmore’s separation is one of the most terrible events of the entire series. Emily has convinced herself that she needs to get out there and play the field, so she gets really flirty with Simon McLane.

Emily and Simon’s date looks elegant with the twinkly lights and the intimate outdoor setting, but it’s all wrong. Emily is forcing herself into a new relationship when she still has the love of her life, Richard, out there!

6 Zach & Lane

Zach Lane First Date

Zach and Lane are happy on their first date, but it’s still one of the worst. All they do is sit at home and eat and watch TV. It’s not too far off from Rory’s first date, but at least Mrs. Kim isn’t present.

At the end of the evening, Lane and Zach weirdly find Brian asleep in Lane’s bed. Zach extracts him and then kisses Lane — while holding Brian over his shoulder! Thankfully, things work out for Lane and Zach, but this is such a strange way to start.

5 Rory & Graham

Rory Graham Gilmore Girls

People’s love lives never go well when Emily Gilmore meddles in them. This is exactly what happens to Rory when Emily introduces her to a longtime family friend named Graham.

Rory goes on a casual first date with Graham but can’t seem to enjoy the night of bar-hopping for thinking about Dean. It’s nothing against Graham, but it probably wouldn’t have ever worked out anyway.

4 Rory & Logan

Richard and Emily’s vow renewal is not technically a date for Rory and Logan, but they sort of turn it into one. The big problem for Rory is precisely that Logan has not asked her out yet. She feels like she has something to prove to him, so she goes into a private room with him for a make-out session. Never mind the fact that her grandparents are having a party for their marriage milestone.

The fact that this is Rory and Logan’s first romantic interaction does not bode well for the rest of their relationship. Logan has his ups and downs, but he’s not good at putting Rory first.

3 Lorelai & Digger

Lorelai Digger first date

When Jason/Digger and Lorelai finally go on a date, it’s so predictable for Lorelai’s character. The fancy restaurant with the mood lighting isn’t working out, so Digger and Lorelai go scavenging in the grocery store for their dinner and eat out front once they’ve made their purchases. Some fans find this romantic, but it’s a bad combination.

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Getting dressed up only to go buy random food to eat with a slimy man who is out to get the Gilmores…that’s pretty bad. It’s more inexcusable seeing that Digger is one of Lorelai’s worst boyfriends ever.

2 Rory & Trevor

After her break-up with Jess, Rory optimistically gives dating the old college try. She goes out with a classmate named Trevor, and the date is comically bad. Trevor and Rory have absolutely nothing to talk about. They have English class together, but conversation topics outside of school are slim. Neither Rory nor Trevor knows what to talk about, but he looks like a nice guy.

1 Sookie & Jackson

As much as some fans love the relationship between Sookie and Jackson, it’s safe to admit that the couple had a rough start. Their first real date is a double date, so they’re already short on alone time. Lorelai gets stuck with Jackson’s cousin, Rune. The entire conversation is awkward and uncomfortable, but it still brings Jackson and Sookie closer together.

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Updated: November 23, 2020 — 3:00 am

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