This is not the time to nag or rant about your boss adding extra work to your already-overflowing to-do list. The more you're there to listen without judgement and without interjecting to tell him he forgot to take out the trash, the better he'll feel. He needs to know you care about him and that you're there for him, not that his tie is all wrong for the shirt he has on (even if it is).
Be sensitive enough to know when he needs you. You're not expected to know what to say or do to make him feel better instantly. You should know, however, when to bail on your girls' night out to stay in and be there for your partner. You should sense when to avoid a long-winded rant about your mother and instead ask him how he feels and if you can help.
Remind him of all the things for which he should be thankful. Unhappy people tend to forget about what they have accomplished and instead focus on missed opportunities, past failures and everything they feel they should be doing but aren't. It's your job to shine a spotlight on his strengths, skills he can offer and personality traits that make him stand out. He may not listen right away, but your words will sink in and start to make a difference.
Offering him encouragement can go both ways. On one hand, the ideas you put forth might never have crossed his mind. But on the other hand, a pep talk can sound like a lecture to someone who isn't feeling very cheerful. The key is to gauge his mood before you list all the things he should be doing to make himself feel better. Test the waters with something simple; if he seems receptive, keep going. If he shuts down, put the advice on hold until he's more open to hearing your ideas.
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