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Mostly trial and error using pythex.org for python, regextester.com for c/c++, or rubular.com if you're coding in ruby for some reason. Source: over 1 year ago
There's a free app for macOS too: http://reggyapp.com. Source: about 2 years ago
rubular - A ruby based regular expression editor
RegExr - RegExr.com is an online tool to learn, build, and test Regular Expressions.
RegexPlanet Ruby - RegexPlanet offers a free-to-use Regular Expression Test Page to help you check RegEx in Ruby free-of-cost.
Expresso - The award-winning Expresso editor is equally suitable as a teaching tool for the beginning user of regular expressions or as a full-featured development environment for the experienced programmer with an extensive knowledge of regular expressions.
RegEx Generator - RegEx Generator is a simple-to-use application that comes with the brilliance of intuitive regex and is also helping you out to test the regex.
RegexMagic - Use RegexMagic to generate complete regular expressions to your specifications by using RegexMagic's flexible patterns, instead of the cryptic regex syntax.