Was it wrong of me to “like” a Facebook post in which a pal mourned the end of a long-term relationship? I think she’s better off without the jerk.

Having occasionally come up snake eyes in the game of love, Mr. Know-It-All understands firsthand that a broken heart can fog the mind. Have you ever tried to do your taxes or solder a circuit board mere hours after receiving an “It’s not you, it’s me” speech? Let’s just say emergency personnel were required. In such a frazzled state, your bummed-out friend might not have realized that your button-clicking commentary was meant to be supportive. And even if she did, she probably didn’t appreciate your lazy way of chiming in. According to a 2010 study by American and Dutch researchers, Facebook users generally have a low opinion of the Like button. Respondents “argued that if people had nothing sensible to say, they should not simply click ‘like’ to be a part of the conversation.”

Should any of your Facebook friends ever find themselves on the romantic skids again, eschew the Like button and make a supportive comment instead. Or, better yet, send a private message in which you point out that her ex is a knuckleheaded scoundrel unworthy of having his tongue used as an ashtray. Nothing cheers up the heartbroken like a bit of well-phrased bile.

As a history buff, I sometimes tweet links to 19th-century cartoons that are pretty racist by today’s standards. Do I need to warn my followers that they might be offended if they click through?

Because of the images of Caligulan excess they typically precede, Twitter content warnings have come to signify raunch. Search the service for the acronym NSFW and you’ll see that links bearing this caveat often lead to fare too vulgar for Skinemax. If you include a similar warning in your tweets about the odious cartoons of yesteryear, then you’re tacitly lumping those images into the same category as the three-way scenes from On Golden Blonde. And that just doesn’t seem right.

“Those cartoons are part of United States history,” says Michael Waltman, a communications professor at the University of North Carolina at Chapel Hill who studies hate speech. “Treating them as taboo because they offend modern sensibilities can become a way of ignoring parts of our own history that we prefer to forget.” In other words, don’t give your most sensitive followers a convenient excuse to avert their eyes; we all need to remember how far America has come, so that we can ponder and debate how far it has yet to go.

Though you needn’t mar your tweets with explicit warnings, do pay close attention to the context you provide. Use your 140 characters to explain why you’re sharing the cartoons, and note that you condemn their sentiments. If your text amounts to little more than “Hey, check this out,” you’re bound to upset folks who don’t have your historical perspective. When tweeting potentially offensive material, you risk a mighty backlash unless you take a stand—if you can’t provide the appropriate context for your link within about 100 characters, maybe it’s time to look into Tumblr.

My startup finally turned a profit, so we’re throwing a party. Should we invite one of the early partners who left—without equity—when things looked grim? Or will that seem like a slap in the face?

You seem to have put too much stock in one of Morrissey’s most misanthropic lyrics: “We hate it when our friends become successful.” Perhaps that’s true in the tiny world of Mancunian rock stars, but it doesn’t necessarily apply to the rest of our species. There’s a chance your former partner doesn’t begrudge you your success—or, at the very least, that he isn’t obsessing over what could have been. It may be difficult to understand this, since you’re sealed inside the startup bubble, but some people believe there’s more to life than rounding up capital and perfecting prototypes.

Even if intense envy is gnawing at your ex-colleague’s heart, excluding him from the invite list could make the situation worse. If he ever learns he got left out, he’ll only grow bitter. (Anyone who has seen The Social Network knows that there is nothing less desirable than a battle with a former partner.) So, no matter how your business relationship ended, take the high road and ask him to the shindig.

But to head off potential rancor, try to make your former partner feel special. “Include a personal note in the invitation stating that you recognize his contribution,” advises Shashi Dosaj, founder of the California Institute of Etiquette, which schools executives on business protocol. And keep a close eye on the guy if he actually does show up—you definitely don’t want him shouting secrets into the DJ’s microphone after his ninth mai tai.

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