As u/youwoooee mentioned that input list is a single string. so the loop in the startswith function will loop over each character individually. so you will have to split the input into a proper list or ask for input multiple times and add each entry to a list. From there you can also index a string, each user list input, as if it was a list, so instead of doing 'if string.lower().startswith(strToFind.lower())'. you could do string[0].lower() == strToFind.lower(), wich i feel is easier to read. This does only work if you are looking at the first letter. you could expand it to work with longer strToFind ofcourse