Keeping Self-Deprecating Donna in Check
Question: What is the best way to respond to a friend that always speaks ill of herself or puts herself down? I can't always be trying to make her feel better. I think it's just a way she makes conversation, but it's exhausting.
Answer: If self-deprecation is her primary means of communicating, then her conversation skills need as much work as her self esteem.
Treat her like anyone else who was talking smack about a friend: Put her in her place. The next time she kicks off a pity party, be like: "I'm sorry, but that's my friend you're talking about. I think she's great and would appreciate if you didn't speak ill of her while you're with me."
If you're ballsy, deliver it matter-of-factly for maximum impact. If you're worried about reception, say it in a borderline jokey way. She'll look at you like WTF? either way, but will have to pick up the words you've just laid down nonetheless.
The sad truth is that it's very difficult to compliment or cajole someone into feeling good about herself. Your efforts are best spent encouraging her to focus on the positive by nipping the negativity in the bud when she's with you. If that means flat-out changing the subject at times, so be it.