I just came across this article and found it to be really interesting, and something that comes up here quite frequently. It's something I can relate to on a personal level as well in a multitude of ways. Definitely worth discussing.
Stop cheering me up: Some people don't want to hear it
In a series of six scenarios involving some 1,000 participants ages 18-30, researchers found that people with low self-esteem don’t want to hear your platitudes, and would prefer friends and loved ones see them as they see themselves. “Those with low self-esteem actually reject the so-called ‘positive reframing,’ or expressions of optimism and encouragement, most of us offer to them,” says lead author Dr. Denise Marigold, an assistant professor at Renison University College at Waterloo.
Despite good intentions designed to boost spirits, people with low self-esteem “are simply more comfortable wallowing” in their misery, she adds. “What we think is well-intentioned support is really alienating for them. They feel as if people don’t understand their issues and don’t accept their feelings. It almost demonstrates a lack of caring.” ... The researchers do want to be clear that validating negative thoughts and feelings doesn’t mean you are free to say, “Yeah, you are a loser,” to a friend who is feeling poorly about a situation. Rather, it’s a more productive to simply acknowledge the person is upset.
For many individuals this is something we know. When we're upset, sometimes we just need to chew the cud and wallow in it for a while. We'll want support or something to cheer us up, but getting a spray of "joy! happiness! love!" in the face usually makes you feel much worse than before. It ties into mindfullness practice as well. Where one is supposed to acknowledge the feelings we feel. Not supress them, or invalidate them.
Of course eventually one needs to stop wallowing and do the best they can to move forward, and it's interesting to consider the implications of induldging someone with this, and where the line is where it goes too far.