I've written from time to time (including this post about memorializing him) about the death of my best friend, as it was one of the formative experiences of my life. I learned a lot from his demise, and carry many of the memories with me to this day - and I use a lot of those lessons in my job as a therapist.
One of the most important and long-lasting lessons I learned from that terrible time was that it's not always such a great idea to try and cheer someone up. I heard so many versions of "it's going to be okay!" and "he's in a better place!" and "it's all part of God's plan."
What I didn't hear, at least until his brother said it to me, was "Wow, you must really be hurting. You guys were so close." And that was exactly what I did need to hear. I figured out quickly enough that the people who were trying to cheer me up were doing it mostly for their benefit, not for mine. I'm a cheerful guy. Seeing me grieving threw them off. It made them feel weird, and they wanted me to cut it out. They weren't being malicious about it, or likely even making a conscious choice - but it was clear that it wasn't okay for me to just be there in my grief in front of them.
Going through that has changed what I do when someone is showing emotion. Greg's death came as I was training to be a therapist. Maybe that was his gift to me - his passing solidified and made real the lessons I had been learning in the classroom. No longer was I in a hurry to cheer someone up, and that holds true today both in the therapy room and out.
A simple "you sound sad" or "looks like things are tough for you right now" can really help someone just expand into that space where they're holding their feelings. No need to ask questions ("are you all right?" puts someone into their head as they try to figure out an answer - "you look sad" lets them stay in their heart). Simply let someone know you see them, and you are okay with what you see. This is another one of those easy "therapy tricks" that you can bring into your everyday life to help you strengthen relationships and open yourself to what's really going on with people.
Next time you feel the urge to cheer someone up, ask yourself whether you are doing that for them, or for you. And, make the conscious choice to let them feel what it is they need to feel. In the short run, it may be a little uncomfortable until you get used to it. In the long run, you'll find out how satisfying it can be to give people such a simple but powerful gift.