Roast Me. Don’t Hold Back.
A friend of mine recently posted about asking ChatGPT to roast him.
It was brutal, but funny.
So I thought I’d play along.
I uploaded this picture and asked ChatGPT to “Roast me. Don’t hold back.” and this is what it said…
First off, nice effort with the “I’m trying to look tough” pose. I see the beard is in full force—are you auditioning for the next season of “Duck Dynasty”?
That backward hat really says, “I’m 15 at heart.” And that tattoo? Bold choice; did you let a toddler design it? It’s definitely giving off some “doodle gone wrong” vibes.
I love the black shirt; it’s a classic. Did you get it from the “Dad’s Wardrobe Essentials” section at Target? And the bracelets? Nice touch. Are they part of the midlife crisis starter pack?
Overall, you’ve got the “tough guy who spends too much time on Instagram” look down perfectly. Keep rocking it!
Not one to rest on just one dataset (I love testing), I asked ChatGPT to do it again with a different picture. I uploaded this picture and asked “Roast me. Don’t hold back.”
Alright, round two:
I see you went from “bearded tough guy” to “I might be an aging rock star, but I’m still trying to be cool.” The hair’s got that “I just stuck my finger in an electrical socket” vibe—bold choice.
The beard is giving strong Gandalf vibes, but in a “I’ve given up on the magic” kind of way. And nice touch with the necklace—did you steal that from a medieval reenactment fair? It really completes the whole “hipster grandpa” look.
And again with the black shirt, I see. Did you buy them in bulk? Or is it just to match the dark abyss of your soul?
Keep up the good work; you’re really nailing that “I refuse to age gracefully” look!
Being a glutton for punishment, I figure “third time’s a charm” so we did it one more time… and I think by then ChatGPT was starting to have too much fun at my expense…
I uploaded a picture of me speaking from stage at John Michael Morgan‘s ACHIEVR Live event in Nashville, Tennessee and invited ChatGPT again to “Roast me. Don’t hold back.” and I think you’ll really enjoy this one.
Alright, let’s dive into this one:
First of all, Lee, that backdrop photo is giving me major “I’m trying to look mysterious, but really I’m just squinting because I can’t find my glasses” vibes.
On stage, you’ve got the classic “motivational speaker” look down. The black shirt again—are you sure you’re not just a floating head in all your photos? And is that a kilt you’re rocking? Bold move. I guess nothing screams “I’m serious about achieving” like showing off those knees.
The belt situation, though—what’s going on there? Are you carrying survival gear in case the audience doesn’t buy into your speech?
And the whole setup—LIVE, ACHIEVE, LEAD—sounds like you raided the nearest gym for inspiration. But hey, you’re up there doing your thing, and that’s what counts. Just maybe next time, skip the “stern librarian” photo pose.
In the end, I believe life’s too short to take yourself too seriously.
Whether it’s questionable hair choices, mid-life kilt phases, or those photos that scream ‘wannabe philosopher with a mortgage,’ we’ve all been there.
And that’s the beauty of it.
So, take the selfie, wear the kilt, squint dramatically into the distance, and laugh at yourself while you’re at it. Because the people who know how to laugh at themselves live lighter, connect better, and leave the room happier.
Now go out there and embrace your perfectly imperfect self.
And remember, no one’s taking notes…
Except me, for my next roast blog.