5 Other Celebs Jennifer Aniston Could Have Ended Up With

Jennifer Aniston finally seems to have found the man she’ll spend the rest of her life with. On Friday, screenwriter and actor Justin Theroux popped the question on his birthday, and his girlfriend of a little more than a year enthusiastically said yes. The official announcement made the rounds last night, and now, it’s just a matter of planning all the details and, of course, staying together.

There’s no reason to think the happy couple won’t be able to make it work. By all accounts, they fell in love almost immediately and have been spending as much time as possible together ever since. Pop Blend wishes them nothing but the best moving toward the future, but for the time being, let’s take a look back at five other famous men Aniston was involved with…

Brad Pitt

Every list of former Aniston loves has to start with Brad Pitt. The two began dating in 1998 and were married in the summer of 2000. For almost five years, they were widely considered a shining example of two famous stars who sacrificed to build a beautiful, longterm relationship. Unfortunately, it all imploded amidst rumors of Brad not wanting to have children and possibly cheating with Angelina Jolie. In one quick swoop, Aniston went from the girl millions were jealous of to the girl nearly everyone felt bad for, and that shift in perspective followed Jen as she worked her way through all her post-Brad relationships.

Vince Vaughn

Vaughn was Aniston’s first serious post-Pitt relationship. The two met on the set of The Break Up during the summer of 2005 but initially denied anything was going on. After pictures emerged of the two kissing in Vince’s beloved Chicago, they were a bit more open about what was going on, especially after engagement rumors began making the rounds. They each feverishly denied there were plans to move forward anytime soon, and those claims were validated when they officially broke up after a little more than a year of dating.

John Mayer

Thanks to John Mayer’s reputation as a bit of a womanizer, we tend to forget how serious this relationship seemed while it was happening. Aniston was going through a phase in which she was kept giving interviews about how not all relationships need to last forever, and he really seemed head over heels in love with her. They ultimately made it a little more than a year before they permanently separated, either because he was too open about his personal life or because he was ready to move on, depending on what sources you believe.

Bradley Cooper

Like John Mayer, Cooper has a reputation for preferring fun over serious, longterm relationships. The Hangover star was linked to Aniston all the way back in 2009 and then again in 2011. Since neither has really addressed the dates publically, we don’t know whether there was ever any legitimate attempt to make this work from either end, but if public opinion is any gauge, it’s probably a good thing this one didn’t last. After Brad left her, sympathy for Jen was at an all-time high. The goodwill carried through the Vaughn relationship too, but once Cooper and Mayer entered the fold, many fans began to wonder if she was trying to find lasting happiness or shooting to have transient good times.

Adam Duritz

After the success of Counting Crows’ August And Everything After, lead singer Adam Duritz was a hot commodity. He was spotted frequently in and around Hollywood hotspots and linked to several beautiful actresses, two of which were oddly, Aniston and her best friend Courteney Cox. At the time, observers thought Jen and Adam had a legitimate shot of taking their relationship to the next level, but years later, it was discovered the two were a whole lot less serious than anyone thought. In fact, they never even slept together. Still, it’s a worthy piece of trivia and a fun what-would-have-happened-if.