I guess if you stand too close to somebody for too long, you might be mistaken for them, despite being completely unrelated. Some words have actually gotten people--politicians, teachers, etc--into trouble or fired, simply because the words stood to close to bad words in the dictionary.
Here's some pairs of definitions--one innocent, one less savory. Guess the troublesome words.
1. Stingy, derived from OE word for "miser"/ socially unacceptable word for person of African ancestry.
2. Educational / prone to molesting children
3. A word that sounds similar to another word / a person attracted to members of the same sex
4. A problem that gets worse, and more inescapable the more you try to deal with it, derived from elements in African and/or Native American folklore / socially unacceptable word for person of African ancestry.
Highlight for answers, with references:
1. Niggardly. (a wikipedia list)
2. Pedagogical. (possibly an urban legend...)
3. Homophone. (a newspaper report)
4. Tar baby. (an editorial)
It's sad to see a word, through no fault of its own, fall into disrepute and disfavor. Ultimately, though, I have to own that the language is not what I want, or what is in the dictionary, but what people speak. As always, I'd be amused to see any of your contributions