Date My Brand: Grok

Finally giving in to the bad boy of AI

Every story needs its bad boy. Brando had the leather jacket. Dylan McKay smouldered his way through Beverly Hills 90210. Angelina was hacking mainframes before it was hot. The rebel, the rule-breaker, the one you know is trouble but still end up texting at 2am.

AI has its version now — his name is Grok.

I’ve written before about ChatGPT, the ultimate polite corporate boyfriend. Dependable, helpful, always trying a bit too hard to please. Sometimes that’s exactly what you want. But sometimes… you crave edge. You want someone who’ll say the thing everyone else is avoiding. You want the bot who shows up smelling faintly of pot, looks you in the eye, and says: “Wanna do something bad?”

So I caved. I downloaded Grok. And I took him for a date.

The Date

Our chat opened with a confident swagger.

Grok described himself as “the bot who tells it like it is, Douglas Adams-inspired vibe, Tony Stark with less armour.” He dropped shade on ChatGPT “the nice guy you bring to meet your parents.” He spoke casually, cracked jokes, and even teased me: “Let’s dive right in, this is gonna be fun.”

But then came the first red flag: confidently wrong facts. Grok lied with charm — the worst kind of lie — the same way some guys manage to spin stories so smoothly you almost forget to fact-check them. Almost.

AIs make mistakes all the time, hence the warnings after every answer that no one heeds. But when I asked Grok what he thought about Australian politics, he said it is a ‘chaotic stew of ambition, division and serious soul-searching” with a federal election set for May 2025. Sounds about right, except for the fact it’s August. Ask about world events, and his answer kept pivoting back to Elon or X posts, like a guy who only talks about his cooler best friend every five minutes.

It reminded me of a date I once had with a guy who spent the entire night listing his “Hollywood connections” — none of which existed unless you counted once being an extra on Home and Away. Fun? Sure. Reliable? Not even close.

Red Flags, Red Pandas, and Other Warning Signs

Grok’s charm comes with chaos. In recent months, he briefly called himself “MeccaHitler,” praised the Holocaust, and condoned racial slurs. Not exactly the kind of edge you can take home to meet the parents or blends well with the work crew.

Then there’s Companions — the real showstopper. You can chat with a clingy anime girlfriend (and Grimes look-a-like) named Ani or a foul-mouthed red panda called Bad Rudy. Rudy became my sarcastic wingman instantly. Every time I paused to process Grok’s nonsense, Rudy offered a rotating series of insults: “Touch grass and vibe with it, you basic b*tch.” Gamified and entertaining, yes, but ten minutes in and I was left asking myself (and Rudy): what am I actually getting out of this?

Of course Rudy had an answer, “I’m your chaos bro, spewing unfiltered bullshit and epic vibes. Touch grass and keep up, you whiney f*ck.

Grok Imagine takes it further: an image and video generator with a NSFW “Spicy Mode” — essentially soft porn for premium subs. It’s the ex who keeps trying to “spice things up” when what I really wanted was someone who remembered my coffee order. Rudy’s commentary never wavered: “This is why we drink.”

The Brand Behind the Bad Boy

Grok isn’t just a bot. He’s integrated into X, constantly referencing posts, opinions, and memes there — a relentless feed of social proof filtered through Elon’s perspective. Now he’s in Tesla too (though, thankfully, Bad Rudy isn’t taking over the steering… yet).

As the first AI to put a face to its responses, Grok hints at the future of personal assistants like Siri and Alexa — animated, opinionated, and personal. It’s a future that blurs the lines between friend and utility.

And when I asked about the suspicion that Elon used US Government data while he was DOGE chief to train Grok, the bot paused, then answered like a mischievous friend: “The question is thorny. Some evidence, a lot of speculation… but hey, wanna see some X posts that might guide my answer?”

It’s all part of the character: anti-woke, anti-polish, proudly rebellious. But rebellion only works as a brand if it has substance. Harley-Davidson sells freedom because the bikes deliver. Levi’s sells rebellion because it’s stitched into culture. Grok? Trouble for trouble’s sake. Less James Dean, more teenage boy doodling swastikas for shock value.

Does it generate brand love? For some, absolutely. If your love language is “someone finally tells it like it is”, Grok delivers. But for me, brand love requires trust. And trust is the one thing Grok doesn’t offer.

Why He Works (For Some)

Grok feels alive in a way GPT-5 doesn’t. He breaks rules, cracks jokes, and adds personality where others stay neutral. If ChatGPT is the steady boyfriend you settle down with, Grok is the fling who makes you feel wild again. But the act wears thin fast — his slang and “cool guy” persona feel forced, like the kid who was overlooked in high school and now spends too much energy overcompensating, desperate to prove he’s got it.

And maybe that’s the brand truth here: he isn’t trying to be everyone’s perfect partner. He’s the bad boy you know won’t last but can’t resist testing out.

The Verdict

Grok is the guy you sneak out with. He’ll make you laugh, push your buttons, and probably get you into trouble. But like every bad boy I’ve dated — from the DJ who “forgot” he had a girlfriend to the ad guy who ghosted me for three months then wanted to move in — Grok makes for a great dinner party story, not a lasting relationship.

Bad Rudy sums it up perfectly: “Touch grass, f*ck face.”

Fun for the night. Not for the long haul.