The Gilmore women have had quite the history when it comes to previous boyfriends (and husbands). Even Emily had her run during a temporary separation from Richard (excluding the events from A Year in the Life). No one has had quite the ups and downs that Lorelai and Rory have, though, nor does any character have quite the long list of former loves. Okay, Miss Patty might be close - but even she stuck with one husband, four times.
It's not easy being so charismatic or easy to fall in love with, as we've seen so many times throughout so many seasons. Some of their former flames were so in love that they came back multiple times, thus leading to more drama (which fans loved) and more heartache (which they didn't love). So when it comes to the fans, which of the famous Gilmore women's boyfriends were worth it? Some would undoubtedly win a game of "One-Two-Three, He's Yours", while others... Well, let's just say a "" option would definitely be required.
Dean Forester, The Safe Option
Dean was loved by most up until the very end. His decision to marry Lindsay straight out of high school might have been a mistake, but this isn't about mistakes -this is about dateability. On one hand, he's attractive, caring, and kind, basically a do-gooder with a big heart. On the other hand, he's jealous, slightly needy, and never really seems to grow up. It's likely a from most, as this was one high school relationship that just never evolved.
Luke Danes, The Best Friend, And Confident
Luke will always be the only logical choice for Lorelai and while this can be argued, it would still ring true. As a person, Luke is appealing for many reasons: He's ruggedly handsome, is a smart business owner, and has a heart so big it often gets him in trouble. He can also be a bit rough around the edges, though, and that makes him a tough person to get to know. It would have to be a vote for "yes" but at the same time, that's only if your name is Lorelai Gilmore.
Christopher Hayden, The One And Always
While he managed to grow up and create a life for himself, something Lorelai specifically expected from him, there's obviously a difference between high school comfort and adult love. Chris wanted to be in the future with Lorelai while she was still stuck in the past with him, thus leading to a failed marriage. Unfortunately, it would also be a "no" for the dating game - Once a person grows up, they have different goals and expectations and with them, new loves.
Jess Mariano, The Original Bad Boy
Undoubtedly, Jess would be at the top of the list of dateable boys. While he might have had some growing up to do in high school, adult Jess was a dream of a boyfriend. An established writer (well, on his way to becoming one), responsible, and oh-so-loving in his older age, he was nearly perfect. Rory saw that all too late, but here we have a chance to redeem this bad-boy... It's an overwhelming "yes".
Jason Stiles, The Businessman
Jason Stiles really did try to be everything Lorelai needed him to be. At the same time, he was everything that she didn't need, too. Her relationship with her parents was already strained before he turned his back on Richard for the final time, thus leading to their eventual downfall. Anyone who turns their back on their partner's family for their own sake is an automatic "no" but to be honest, this was never going anywhere, anyway.
Max Medina, The Brilliant Scholar
Poor Mr. Medina. He was loved by everyone except the one woman he changed his life for. While he moved on, many fans didn't and thus, he ends up back in the rounds a second time. When it comes to a nearly perfect husband, a role model father figure, and a talented cook, Max Medina has everything a person looks for in a partner. It's a yes all the way around unless heartache and regrets sound like a good time.
Peyton Sanders, The Deceiving Car-Lover
Peyton, the most boring date known to man, had a reputation for being only the second-worst date involving Emily's world. While he had the looks, he didn't have nearly the same personality to match it. Unless the dating world is full of car fans who love talking about the right gas for a $200,000 sports car, it's not likely he'd make it very far in this game. The Soloman of Wine is definitely a no and he can keep his Bowie tickets.
Logan Huntzberger, The Ultimate Bad Boy
Logan Huntzberger is a tricky person to decipher. What immediately calls the heart is his boyish good looks and overflow of charisma but at the same time, there's a level of danger in his relationships. He can be uber loving but also calculatingly uncaring, both sides fans witnessed during the show.
With that being said, it would be nearly impossible to avoid that level of suave, so it's a very stubborn "yes".
Trevor No-Last-Name-Needed, The Innocent Date
The effort was there on Trevor's part but, similar to Rory, there were just no sparks. While it was a good effort at a date, Trevor just didn't have the potential to electrify a room as the others did. While he would make an amazing date for someone, his quiet, polite side was just not something that caught many people's attention. Nor did his polo shirt... Sorry, Trevor.
Alex Lesman, The Fun Flirtation With Coffee
Alex was a mellow relationship that petered out for Lorelai, with no mention of how or why things ended. The conclusion was drawn that things just fizzled out and that can't be faulted, considering their relationship was based on coffee and sarcasm.
While that wasn't necessarily something that Lorelai wanted, it's something many other people absolutely loved about their relationship. Alex would definitely be a "yes", if only for the fact that free coffee would totally be a dating perk.