gorb | A go library written in pure Ruby | Game Engine library

If someone enters a, you're calling getMeaning which in turn calls get_close_matches. You're then checking if that call has a non-zero-length return value and if it does you do return DataBase[close_match]. That's where getMeaning ends.

You'll never reach the else-part of getMeaning, if get_close_matches produces results. In the screenshot of your question, we can see the results of user input a which make sense like this since get_close_matches finds cat is similar to a.

Disregarding that, you should use startswith if you want to test if a string begins with another string. Also, you don't need elif or else after the previous if or elif has a return and I have changed the names according to PEP 8 section Descriptive Naming Styles.

Here is a possible solution, using a filter which only accepts a close match if the letters are the same as in word: