I'm watching Gilmore Girls and I'm currently on season 2 on DVD seasons and season 6 on ABC Family. Apart from the hilarious story lines and relatable dramas, I genuinely like this show because it's not overly dramatic, the type that would not usually appear in real life. Inadvertently coerced in watching this delectable series, there is one certain thing that stands out: boys. Gilmore Girls has fine taste in men. (Which may contribute to my like to it.) And there is a lot of speculation to whom Rory should have been with at the end of the series run. So I'm giving and pinching in my two cents who should have deserved Rory regardless of the turbulence and ups-and-downs of life.
Dean (Jared Padelecki) was Rory's first serious boyfriend. He was somewhat scruffy and yes, he wasn't as smart or hard-working as Rory, but he was honest, truthful, dependable, and loyal. He genuinely loved Rory and was willing to be with her even when he was legally married to another woman. He loved her and knew that she was the One for him. Yes, he did get somewhat clingy and protective and downright stalker-material creepy when Jess showed up on the scene but that was only because Dean knew that Rory was losing interest in him and attempted to keep her interested. He is the ultimate gentleman and nice boy wrapped up under a cloak of misleading clothing. He was self-sacrificing and was authentic. Rory could be herself with him around--she didn't have to pretend or act around him. And he embraced her quirks. And, he pursued her like a girl should be pursued. He liked her from the moment he laid eyes on her (so did the rest of them...more or less) and he wouldn't let her go without a fight. Plus, he looks mighty fine in a tux. Dean, in my opinion, who I consider the cutest and the hottest of all of Rory's "gentleman callers", should have ended up with Rory because he would make perfect husband material. Also, they were each other's first loves and no one ever forgets about them. You move on, continue life, but you never really forget. Which is clearly shown throughout the series. Plus, he never left Rory; he always stood by her side. Even when they weren't together or had broken up, they still had each other's backs.
Jess (Milo Ventimiglia) was Rory's second boyfriend--the bad boy who avidly read books, which caught Rory's attention and made her heart flutter. There is no doubt that he is cute (even I'm not going to deny it; he's a hottie!) or that he has nice hair or sultry eyes and kissable lips...He is Italian, after all. Dang that Latin blood. I swear, there has to be some hypnotizing power in that blood that makes a girl swoon and sigh over him. He likes to read. A lot. Which is one of his and Rory's primary interest and the fact that he could keep up with her constant quips on pop culture. Yes, he is an amazing kisser and can make you short on breathing. However, he does have commitment issues. He is the reason why Rory and Dean broke up--because Rory and Jess has a magnetic attraction and Dean wasn't blind. Dean did fight, but Rory was defenceless against Jess's irresistible charms. Jess would often run away and he didn't seem to truly show Rory the affection that she deserved. It almost seems as though Jess was cold and hesitant towards Rory in showing public affection (I'm not referring to the lip-on-lip public display of affection). Plus, he left her several times. When he left Stars Hollow for the first time (after he and Rory got in a car accident...which ended Rory in the ER), when he left for the second time, and when he came back, he treated her like crap, only to say I Love You, and then leave. Again. I don't doubt that he had good intentions but I feel as though he failed in displaying them. He worked hard to get Rory and after he did, he display the effort anymore. I think they should have dated once Rory visited him when he opened his own book store/cafe/open poetry club and even once before that, but I don't think he should have ended up with Rory in the end. He wouldn't have made ideal husband material. The though of fleeing must have entered Rory's mind several times if they were married and I'm sure that must have freaked her out. Who knows? Maybe he could have changed. People always change. (Note: Alexis Bledel and Milo Ventimiglia dated for 3 and a half years, from 2002 to 2006, in real life. So there was a real life Rory/Jess relationship. Now that should have lasted for longer and they should have ended up in real life for good.)
Logan (Matt Czuchry) was Rory's Yale boyfriend and he was the playa that was tamed when Rory stepped in the picture. He obviously liked Rory a great deal once he stepped across from perpetual bachelor to committed man. He was quick-witted, genuine, funny, charming, and, yes, rich. But I feel that last quality is something that Rory would have never cared. So what if he can buy her an expensive Hermes bag? Dean gave her a handmade bracelet to show his looove. But, Logan did cheat on Rory several times and while infidelity can be forgiven, it's more difficult when it's done with multiple at the same. I should also mention that Logan was the only boyfriend of Rory's who has cheated on her (Jess and Dean would never stoop so low). I'm certain that he did regret it, that it was an awful mistake, and really loved Rory. It's evidently displayed with him desperately trying to win her back...and succeeding. Of all Rory's bf's, I actually think he's the least cutest (not saying he's ugly, but compared to Dean and Jess, he would find himself in a trifling matter). I do however like the sound of his voice. It's husky and sexy, especially when he rambles and goes on and on, competing with Rory for most-spoken pop culture. The only thing I do not like is when Logan's jealousy flares. It can be uber hot; for him, it depicts his mean and rude side. Even though I think Dean should have ended up with Rory ultimately, when Logan proposed to Rory, she should have said yes. He obviously loved her enough and that much to spend forever together. She shouldn't have feared and took that leap of faith.
Everyone has flaws and makes mistakes. There is good and bad, strengths and weaknesses in everyone. While every boyfriend has certain charms and looks, every one of them had a flaw, a falling character trait that in the end could have determined the termination of that relationship. Notwithstanding, every boy had a quality that should have lasted and Rory should have ended with him...Everyone has their own opinions and it can be fickle. My opinion is that Dean was the ultimate choice, then Logan, then Jess. But hey, this is just my opinion. As much I would like to look at only their exterior (which is a nice view, mind you) and determine their character on that alone (in that case, it would Milo, Jared, and Matt), I have to look at their personalities logically. But, in the moment when I'm watching them on-screen, it seems as that rapidly vanishes away and all I can think of is, "Oh, Jared is so cute", "Milo is super sexy", and " Matt has a way with words that makes my heart go gung-gung". Still, Rory shouldn't have ended alone on the series finale. Lorelei ended up with Luke--Rory should have too.