Wikipedia
Visit a random article on Deletionpedia, which archives pages that were (or might be in danger of being) deleted from Wikipedia: https://deletionpedia.org/en/Special:Random.
Wikipedia
Go to https://en.wikipedia.org/wiki/Special:RecentChanges. Find and follow any particularly large edits on the page to a page that's unfamiliar or intriguing to you.
[Edit size is shown as a number in parentheses; edits that add information are in green and large edits are in bold]
(by protondonor)
Wikipedia
Search your birthday, select the first event and then select the first event. Select the first person mentioned.
(by nahanaeli)
Wikipedia
Go to random.org and generate a random number n between 1 and 500. Visit https://en.wikipedia.org/wiki/Special:LonelyPages and click on the nth page in the list.
(by protondonor)
Wikipedia
Visit the Wikipedia page for something you know quite a bit about. Go to the bottom of the left sidebar and click on a language to view the version of that article in a language you do not speak. Then follow links from page to page on that language's version of Wikipedia, until you find an article that does not exist in English. (Depending on the language space, you will likely either see a list of language in the left sidebar or via a dropdown menu on the upper right hand side of the page). Once you've found a page that does not exist in English (it may take some time), copy and paste the text into Google Translate to translate back into English.
Wikipedia
Go to a random wikipedia article (https://en.wikipedia.org/wiki/Special:Random) then click "view history" in the top right corner, and click the username of someone who has edited the page (the username is right before the parenthetical "talk | contribs" on every line of the page). Skim their profile, and optionally their Talk page (which there is a tab for on the upper left hand of the profile). What's their vibe? Repeat until you find someone you'd want to be friends with.
Wikipedia
follow the instructions to duplicate this google sheet and fetch random wikipedia articles, looking only at the highlighted page with the lowest number of views in the past 60 days.
https://docs.google.com/spreadsheets/d/1SXjQmVs0-eSnmoq37WvUkA_qCKaAkgZTvx6y0tBBP88/edit#gid=0
Amazon
In 2020, Jeff Bezos's net worth increased by $75 billion. In contrast, the average Amazon factory worker will have earned less than $30. Go to Amazon and try to fill your cart with 5 most expensive items you can find. What's the highest cart total you can get?
Amazon
Amazon is used by 197 million people every month.
Visit imfeelingprimey (https://imfeelingprimey.com/) and click the button to generate some random Amazon product links. Click through to an item of your choice and scroll down to the reviews. Find a review that catches your eye, and click on the name of the person who wrote it. Try to find a person with a decent number of reviews on other products. Then close read their purchases and reviews to try to understand who they are as a person.
Amazon
Jeff Bezos wasn't content with Amazon being an online bookstore. He wanted Amazon to become the "everything store"—a store that offered limitless selection and seductive convenience at disruptively low prices. But despite the nickname, Amazon does not truly have everything. Find something in your home, preferably an object of meaning, that cannot be found on Amazon. Then search for it on Amazon anyways and see what you find.
Amazon
Select a book, and insert full sentences from the book into Amazon's search box.
Use Inflact (https://inflact.com/tools/instagram-search/) and filter for users with few followers who nevertheless post. Try different combinations of search terms, follower, and post counts.
Visit a random word generator (https://www.textfixer.com/tools/random-word-generator.php). Generate 6 words. Pick one of the words and the first letter of another (example "tongue" + "hometown" = "#tongueh") and enter it into the search field of the instagram mobile app search tab > see all results > tag tab. choose a tag that has under 200 posts whose name is somewhat inscrutable to you.
Go to your own instagram and click the ‘tagged in’ tab. Choose a photo, click to that person's profile, then their tagged photos. Continue like this, navigating instagram exclusively through tagged photos. Try to find a profile that looks as little as possible like someone you would follow.
Youtube
Search for the Youtube video of a song you listened to on repeat in the distant past. Instead of playing the video, scroll down and read through the comments out loud.
Youtube
Write down interests of yours that wouldn't be obvious to someone looking at your browser history. Visit the Youtube Ad Library (https://app.vidtao.com/#/home) sort by most recently upload date (or low view count), then search for ads related to those interests.
Youtube
Search on youtube for the day and year one of you was born (ex. August 13 1985). Use found text and screenshots from the resulting videos to make a visual horoscope for people born on that day.
Youtube
Visit astronaut.io, a website that plays videos with no views on Youtube
Zillow
Zoom all the way out on the map, remove boundaries, then click the draw button. Draw some random straight lines, then click apply. See what homes appear.
Zillow
Filter Zillow for 0 bedrooms, 4+ bathrooms
Zillow
Search for one of America’s least-populated zip codes (https://localistica.com/usa/zipcodes/least-populated-zipcodes/) on Zillow. If there aren't any listings in the town, click "Remove Boundary" and slowly zoom out until you find a listing.
Zillow
Download an image from a zillow listing, then do a reverse Google Image search. Replace the text portion of the search with site:zillow.com. Then click through to the visually similar images to find houses with similar exterior or interiors.
Zillow
Visit Aesthetics Wiki (https://aesthetics.fandom.com/wiki/List_of_Aesthetics) and select an aesthetic. Enter it into the Zillow keyword filter under the "more" menu (you may want to shorten it ex. rusticcore -> rustic) and see what you find.
Google Street View
Generate random geographic coordinates (https://arc.net/l/quote/tdlzlkfz) and view them in Google Maps satellite view. Zoom in, hide labels using the bottom left layers menu, then find a path in the satellite landscape to follow with your eye. Drag the viewport around, continuing to follow that path, jumping to new paths as needed, until you find a painting you would hang up on your wall. Repeat as needed.