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Givin’ Old School?! Willow Smith Sparks Debate With Question About Dates & The TL Erupts (VIDEO)

Written by on October 12, 2025

Back In The Day? Willow Smith’s Old-School Dating Debate Sends The TL Into Chaos (VIDEO)Back In The Day? Willow Smith’s Old-School Dating Debate Sends The TL Into Chaos (VIDEO)

Roomies, you know Willow Smith always keeps it deep—and this time, she’s got the internet in a full-on debate over dating culture. The ‘Wait a Minute!’ singer hopped on Instagram with one of her signature thought-provoking questions, and let’s just say… people had feelings.

RELATED: Not That Deep? Willow Smith Clears The Air After Social Media Misses Joke In Her Previous NSFW Post (WATCH)

Is Traditional Dating Dead? Willow’s Question Sparks Debate

In a now-viral Instagram Story shared on Friday (October 11), Willow Smith asked, Am I just delusional or people asking other people out on dates is kinda like old-school? She continued, I don’t even remember the last time someone was like, ‘Hey, would you want to go on a date with me?’” The post quickly made rounds online, with some agreeing that the art of courtship has faded, while others say Gen Z might just be overthinking it. Either way, Willow’s casual question turned into a full-blown convo about whether traditional dating is a thing of the past. “I’m gonna start saying it again,” she added.

“Okay, yeah, people still hang out in a romantic way, obviously, but like, to explicitly ask someone out on a date and use those specific words — especially someone you don’t really know that well — that’s a different kind of thing. Like, ‘Would you wanna go out on a date with me?’ When’s the last time someone asked you that?” Willow continued.

One Question, And The TL Went Off!

Roomies didn’t waste any time running to The Shade Room comment section with their two cents. Some folks agreed with Willow, saying traditional dating really is a thing of the past. But others couldn’t help but bring up her famous parents, with comments about their relationship history.

One Instagram user @kweenmocha said, “Willow just be high and sayin sh*t.. i get it. 😂”

This Instagram user @ishellee wrote, “Facts… cuz “let’s link” don’t give me butterflies 😂”

And, Instagram user @_jolinajolie added, “She right !! They’d say anything but ‘would you like to go on a date with me ?’

While Instagram user @msamerica_iam shared, “Yea Willow. Unfortunately your generation is different that way 🤷🏾‍♀️”

Then Instagram user @p_horne7769 said, “People in the comments DEFINITELY didn’t pass English at all! 🧐😣 she is basically saying… it will be dope to start back asking people out on dates.

Finally, Instagram user @theshoekai commented, “Bring back old school chivalry. It’s a lost art!!!

Willow Has Been Keeping The TL Guessing, Okay?!

Now y’all know this ain’t the first time Willow had the internet clutching pearls over her takes on love, dating, and everything in between! As previously reported, The Shade Room caught her addressing the reaction to a wild IG Story where she posted a crying selfie with the caption, Who ate all the p**y?”*—and let’s just say, folks were left confused and a little bit shook.

But Willow cleared it up in a follow-up video, calling out the internet for doing the most. “Y’all so dense y’all forgot funny existed,” she said with a smirk. “Y’all like molasses—slow. But also sweet though, be sweet too. But it was funny, s**t.” And just like that, she reminded everyone that she’s going to say what she wants—and  stay unapologetic every single time.

RELATED: Wait, What? Willow Smith Turns Heads With NSFW Social Media Post (PHOTO)

The post Givin’ Old School?! Willow Smith Sparks Debate With Question About Dates & The TL Erupts (VIDEO) appeared first on The Shade Room.


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