10 Questionable Dating Choices In Gilmore Girls

Gilmore Girls is the show that covers it all – family, friendships, relationships, everyday life, big events, and seasonal changes, to name a handful of things. Dating is not the only focus of the series, but characters certainly spend a fair amount of their time on dates.

Dating on Gilmore Girls can lead to long-term relationships or marriages, or it can dissolve more quickly than that. For all the romances on the show that fans love, what are some of the most questionable dating decisions?

10 Paris: Asher Fleming

Paris’s dating relationship with Asher Fleming is one of the saddest on the show. The distinguished professor is an old friend of Richard Gilmore’s, which makes it even weirder that Paris dates him as an undergraduate. It was never appropriate for Paris to date a professor at Yale, but it was tragic to watch her grieve Asher’s death.

9 Rory: Logan

Rory’s boyfriends sharply divide fans, but Logan Huntzberger is obviously a questionable choice for Rory. Dating Logan isn’t easy for Rory because she never really knows where she stands with him.

Even once they solidify the exclusivity of their relationship, Logan and Rory still have problems. They’re bad influences on one another, and Logan isn’t serious enough about their future until it’s too late.

8 Luke: Nicole

Luke and Nicole’s dating relationship might have benefited from a longer timeframe of actual dating, but the pairing is still questionable.

After meeting through Taylor Doose (the first bad omen), Nicole and Luke go on a cruise and spontaneously get married. Their relationship is over before it really begins, ultimately ending in divorce after Luke and Nicole try to live together.

7  Lane: Dave Rygalski

Fans aren’t in agreement on whether Lane should have ended up with Zack or Dave. Dave is a nice guy, and he and Lane have some good times in the band with Brian and Zack.

While Lane and Dave’s dating days are sweet, Dave moves away and ultimately doesn’t work out as a long-distance boyfriend for Lane. Maybe she and Dave never should have dated in the first place, or Dave should have stayed in Stars Hollow for Lane.

6 Paris: Doyle

Paris and Doyle seem like a good match at first, but their neurotic tendencies eventually multiply into a funny but unhealthy relationship.

Jamie was a much more even-keeled guy for Paris, and although Doyle is able to put up with Paris, he can’t meet her needs for the long haul. The former lovebirds are divorced in the 2016 reboot.

5 Lane: Zack

Lane Kim deserves only the best in life, but she doesn’t get that in her relationships. After Dave, Lane pairs up with Zack, who can be a very awkward person.

Zack gives mixed signals and tries to pressure Lane into more than she is comfortable with. Zack can be quite moody, and while they are happy in their marriage, Lane and Zack aren’t exactly the perfect couple.

4 Lorelai: Christopher

Lorelai and Christopher definitely needed to date the first time; otherwise, the series couldn’t exist! It’s their dating during Gilmore Girls that is much more problematic.

Christopher is known as an absentee dad whose promises to “be around more” are too thin. Not only do Lorelai and Christopher date again; they also get married. Fans know how terrible of an idea this is, and the marriage is soon over. Luke isn’t perfect, but Christopher is even worse.

3 Emily: Simon McClain

When Richard and Emily have their marital troubles, Emily decides to play the field a bit. Her candlelit dinner outside with Simon looks pleasant, but it’s all wrong.

After all they’ve been through, Emily and Richard should have tried harder to work out their problems before seeing other people. Their relationship may not be perfect, but it certainly isn’t helped by Simon McClain.

2 Lorelai: Digger

Jason “Digger” Stiles is one of Lorelai’s worst boyfriends on Gilmore Girls. Their memorable grocery store picnic date aside, Digger and Lorelai are difficult to watch.

It doesn’t make any sense for an independent woman like Lorelai to date an entitled man like Digger. The fact that Digger is out to ruin Richard’s business shows that he can’t be trusted, even if he puts on a charming face.

1 Rory: Dean

The first season of Gilmore Girls would have been quite different if Rory and Dean had never dated. They are presented as the perfect teenage couple until Jess arrives and complicates everything.

Rory and Dean’s first round as boyfriend and girlfriend might not be the biggest mistake, but their second attempt at a relationship is horrible. Rory confides in Dean as a friend and gets a little too close to him, which soon erodes Dean and Lindsay’s marriage. Maybe that strange first date with Lorelai at home was a sign.

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