When I'm writing I spend considerable time looking up the meanings of words in the Merriam-Webster online dictionary,
No, I spend my time looking up common, ubiquitous words that I already know the meanings of, or think I know the meanings of, because when in slightest doubt I like to make sure that a word means precisely what I think it means - surprising how often I find that a word's meaning isn't precisely what I thought it was - and that it's the strongest word I can use to string together the words preceding and following it.
To that end it's not unusual for me to look up the meaning of a word, then not completely happy, look up the word's synonyms, then choose a synonym and look up its meaning, then choose another synonym and look up its meaning as well, then look up the meaning of a synonym of the synonym, then the synonym of the synonym of the synonym, then go back and re-try the original word and then start the process over again. I'm like someone standing before a mirror attempting to put together an outfit from a stack of clothes, trying on then discarding then trying on again then discarding again piece after piece until the whole outfit looks and fits perfectly...or else giving up and just making do, which is what I sometimes end up doing when, try as I might, I can't find the perfect word.
All of this to say: When I heard about Samantha Bee's use of the word she used to describe Ivanka Trump...well of course it's not that I'd never heard that word before and of course I knew what the word meant, or what it was meant to mean by Samantha Bee, or what I thought it was meant to mean by her - not a nice word to describe anybody, though mayhaps Ivanka Trump merited it,
...under the circumstances.
So I looked it up on vocabulary.com and here's what I found:
However "feckless," according to vocabulary.com, means "'ineffective', but is also used to describe someone who is irresponsible, incompetent, inept, or without purpose in life."
So that word works much better to describe Ivanka Trump.
As for the other word that Samatha Bee called Ivanka Trump, the word that she used "feckless" to modify, the "c" word, as we polite folk prefer to call it, that particular pattern of letters has been designated a filthy obscenity, though if one inserted an "o" before the "u" then it would be a fine word, as it would be if one substituted an "a" for the "u" and inserted an apostrophe before the "t." But those four letter as they stand, are an X-rated insult in the English language.
That is to say, as I've always understood the definition of that word.
(Though, I don't know, just taking that word on what it sounds like it should mean, to me the word "cu**" always sounded like some kind of fur hat, like the racoon skin cap Davy Crockett wore. But, of course, as I didn't make up the word, I don't get to say what it should mean).