Rest Easy, Jeeves!

Ask Jeeves hung up the shoes this month.

It wasn’t a breaking news but it triggered something nostalgic in me.

It was launched when Google was still fascinating us. Google showed search results, but Ask Jeeves actually answered the questions.

Who knew that after 30 years, Google will answer questions and Ask Jeeves will fold up.

Ask Jeeves had a personality, still remember that butler logo. In 1997 that felt genuinely magical.

This is the second time I’ve felt this specific kind of sadness.

The first was when Yahoo shut down GeoCities in 2009.
I had a GeoCities page. A lot of us did.

It was so exciting to build an HTML page using Dreamweaver, upload the folder on Geocities and watch it live in Internet Explorer!
Terrible fonts, tiled backgrounds, hit counters at the bottom, and it was the most exciting thing in the world to a kid who had just discovered the internet.

I think I was using IE4 that time :-)

When Yahoo pulled the plug, something quietly disappeared that you couldn’t get back.

Then I remember writing blogs on Blogger - but I never liked it. I moved on to MSN Spaces. It was visually nice, had widgets and since it was coming from Microsoft, I had a trust on it.

Sadly, it was also shut down in 2010 :-(

Later I had a good attachment with Yahoo Answers, and it also shut the doors.

Today, Ask Jeeves feels the same way to me.

When the technology from your teenage years disappears, it’s not just a product closing.
It’s a little piece of how you first understood the world, gone.

Here’s what makes it sadder from a product perspective though.
Ask Jeeves was right.
Natural language search, asking questions the way humans actually speak, that’s exactly what the entire industry has converged on in 2026.

ChatGPT, Perplexity, Claude. They’re all doing what Ask Jeeves was trying to do in 1997.

The vision was correct. The technology just wasn’t there yet.

And instead of holding on to that vision, they dropped Jeeves in 2006, rebranded to Ask .com, and tried to out-Google Google. You know how that ended.

They had the right idea 30 years too early. And they gave it up right before the world was finally ready for it.

Rest easy, Jeeves.

I own a Mac now but sometimes, I still feel like assembling a Windows PC manually, partitioning hard disk, installing OS on it, then copying all my MP3 collection and playing that using Winamp player.

Want to live that nostalgia again.