A Diddy Dive Before His Day(s) in Court

Im lighting candles for everyone in the calm before the storm.

When Deanna and I started How to Be Less Old back in 2015, we told youths on our podcast over and over to never take a nude or sexually explicit photo or video — but if you do — to never included your face or any identifying characteristics if you planned to send it out into the digital world. It’s simply not safe.

Diddy has done some unspeakable things, but one of his glaring oversights has been that he also recorded himself (and others) doing these unspeakable things. And just like your aunties warned, it’s not going to be pretty.

The Diddy news, as much as I wish I could just make it all go away, is just going to be gaining momentum in the months (and years) to come. So, let’s do a dive. Is it deep? No. This is just an introduction to why Diddy is currently sitting in jail and on suicide watch.

Oddly, he said it best himself back in 1999 on Entertainment Tonight saying, “they’re probably going to be arresting me,” about his famed parties.

Now, I’m sure we all have some of the details over the years. We remember the white parties, we know the reality show Making the Band and the group Danity Kane, the clothing brand Sean John. But, I am in no way a fan, an expert, or even well-versed in what terrible things many know that Diddy has done over the years starting at Uptown Records and throughout his many business ventures and relationships.

Did I have a vibe that Puff Daddy aka Puffy aka P. Diddy aka Diddy aka Sean Combs wasn’t a great dude? Sure! I assumed big ego, and likely a narcissist, but I had no idea he was a monster until the Casandra Ventura news broke in November of 2023. Maybe you knew?

I remember talking to a journalist friend that November about the allegations that Cassie made against her ex Diddy in her lawsuit, who she dated on and off from 2007 to 2018, and being stunned and horrified by her account of years of abuse, rape and sex trafficking. The matter was quickly “settled” outside of court within a day. And that just got the ball rolling. Let’s get into it.