‘Gilmore Girls’: Four Times Dean Was So Not a Nice Guy

Lorelai Gilmore often championed for Dean Forester, Rory’s first boyfriend. She insisted, time and time again, that Dean was the best first boyfriend that a mother could hope for. While Dean had his moments of being a sweet and thoughtful teenager, there were plenty of times that he proved he was not nearly as a nice of a guy as Lorelai thought he was. While there were plenty of cringe-worthy Dean moments in Gilmore Girls, we’ve collected just four examples of Dean being a big jerk.

He broke up with Rory in public (twice)!

Dean’s breakup skills aren’t exactly the best. He deserted Rory on the Dance floor screaming that he wasn’t her boyfriend anymore in front of a room full of townspeople. While the townsfolk didn’t seem to react to it at all, it still seems kind of harsh. The second time around, he ended the relationship in front of all of Rory’s Yale pals, right in her grandparents’ driveway.

We could almost give him a pass for his very public outburst the first time around. After all, Rory was totally into Jess and was not trying to hide it towards the end. The second time, however, Dean could have very easily picked a different time to put the kibosh on the relationship.

Being a complete jerk to the wife he was cheating on

Dean’s pursuit of Rory, while he was still married to Lindsay, was pretty rough but going home after you’ve cheated on your wife and screaming at her over a cellphone seems harsh even for the quick-tempered Dean. She really didn’t deserve to be berated right after her husband got it on with another girl.

While Dean and Lindsay’s relationship was supposed to be a cautionary tale of what happens when two kids get married way too quickly, the entire storyline proves that Dean is just not that nice of a guy. Dean’s case isn’t helped by the fact that Lindsay legitimately seemed like the exact type of girl he wanted. She was happy to be a housewife and cook her husband dinner, just like Dean said he wanted. 

Lying to Rory about ending things with Lindsay even if she didn’t find out

Rory is pretty perceptive, so it’s shocking that she just believed Dean when he said he would have ended things with Lindsay whether she found Rory’s letter or not. Dean was lying, though. Hardcore fans will remember that Dean was practically begging Lindsay to work it out with him while she was tossing his belongings out of their apartment window.

It’s obvious that Dean had no intention of leaving his marriage unless Rory was absolutely ready to commit, and even then, we doubt he would have told Lindsay the real reason. He did remain married while Rory was in Europe with Emily, and it’s unlikely he was going to blow up the entire situation unless he had Rory to fall back on.

Dean was totally disrespectful to Richard

Richard wasn’t exactly kind to Dean. He attempted to intimidate the teenager at every turn, but that doesn’t mean Dean had to stoop to his level. Dean could have tried to be nice to Richard, knowing that he was merely acting out of concern for his beloved granddaughter, but that didn’t happen. Dean was especially snarky when Richard questioned the safety of the vehicle that he had built for Rory.