This is a new thing people say when someone does something so incredibly stupid and disappointing to the point where the are feeling to go back im time and stop themselves from seeing that disappointment.
(Or it defines someone's child being a hoe/slut/pornstar/onlyfans creator and actually being proud of that)
Some examples of should've used a condom are:
Example 1: someone who enjoys watching skibidi toilet.
Example 2: someone who does something cringe on the internet or irl
Example 3: someone who spreads their nudes online for people to see