Okay, so I got curious about the whole John Mayer and Jennifer Aniston thing again the other day. It feels like ages ago, right? Decided to spend a bit of time just looking back at what went down. Here’s kinda how I went about digging into it.

Starting Simple
First off, I just went to my usual search spot online. Typed in something basic like “John Mayer Jennifer Aniston dating”. You know, just to get the ball rolling. Wanted to pin down the years they were actually together. Seems like it was mostly around 2008, maybe bleeding into 2009 a bit? It was definitely on-again, off-again for a while there.
Reading Through Old News
Then I started clicking on some of the articles that popped up. Lots of old entertainment news, gossip columns from that time. You remember how much press they got? It was pretty intense. I skimmed through a bunch of those pieces. Trying to piece together a timeline. Saw mentions of them going to events, pap shots of them on vacation. The usual celebrity couple stuff.
Looking for Their Words
I specifically wanted to see what they actually said about it, not just what reporters wrote. So, I searched for interviews. Looked for “John Mayer interview about Jennifer Aniston” and flipped it around too. That’s when I stumbled across reminders of that infamous Playboy interview Mayer gave. Yeah, he definitely said some things back then. Maybe TMI, you know? Aniston seemed way more reserved when asked about it, which kinda fits her style, I guess.
Key Moments and Breakup Talk
I tried remembering specific public appearances. Weren’t they at the Oscars together? Yep, quick search confirmed it. Found pictures from the 2009 ceremony. They looked pretty solid then. Then I looked into the breakup reasons people were throwing around at the time. The articles mentioned stuff like:
- The constant media attention being too much.
- Maybe different places in life, the age difference?
- His tendency to talk openly vs. her being more private.
Seems like a mix of things, which usually is the case, isn’t it?

What Came After
Finally, I did a quick check on what was said after the split. Years later. Found some quotes from Mayer where he seemed kinda regretful about how public he was, especially with that interview. Aniston, from what I could find, stayed pretty classy. Didn’t really dish dirt, just moved on. Respectable.
So yeah, that was my little dive back into that piece of Hollywood history. Just involved some searching, reading old articles, trying to find direct quotes. It was an interesting relationship to follow back then, full of buzz. Just goes to show how intense that spotlight can be. Spent a couple of hours just clicking around, piecing it together from what’s out there online. That’s my process, pretty straightforward really.