I think this boils down to the dilemma of empathy. How much should we use, and how much should we expect from others?
You have every right to feel proud of your accomplishments, and they have every right to be discouraged and even disappointed by them. Just as you will encounter people who you will envy for, or be discouraged by their successes and good fortune.
The dilemma of empathy is always a tightrope walk, and a tug-of-war, and it always will be. Your friends will fail to be empathetic at times, and so will you, but the dilemma is far from unique to the topic of weight loss.
If you were talking about your new baby to a person who had just had a miscarriage, or about your new fabulous job to someone who was just fired or laid off, or any other topic in which your situation is drastically different than the person you're talking to, there's always the risk that it could make both or either side uncomfortable (for either having the good thing, or for not).
I think the "friend you can tell anything" to a degree is a myth. There are people who hide their disappointment and envy well, but you still risk hurting a person when you passionately discuss something you have that they don't -or complain about something they have that you don't.
It doesn't mean that you can't ever discuss these things. It does mean that you always have to play it all by ear. If you notice, or they share that a topic hurts them, then you don't discuss that topic with that person. There are plenty of people you can share with. You don't have to feel sad or betrayed that it's a taboo subject. It's ok for all of us to have off-limit subjects, and to be honest with each other about which they are.
When I first realized that my husband and I were not going to have children because of our health problems, I initially was in denial and to many friends and family, I pretended to be relieved, but internally went through a mourning period for the child I would never raise. It was sometimes hard to hear friends and family and even strangers go on and on about children. I'm sure I had every reaction possible when the baby/child topic was raised, including trying to change the subject, venting about how frustrated and hurt I was with the conversation or how lucky they were to be able to have children, or saying nothing but feeling horrible and two-faced for pretending to be happy when I was only jealous.
Weight loss is no different than any other potentially-sensitive topic. You adjust what you share to your audience. Complaining about your leaky roof to a homeless person (even if their poor choices led to their homelessness) isn't going to get as much empathy as discussing it with someone who is currently having the same problem.
In an ideal world, even the homeless guy would say and feel "I'm so sorry to hear about your troubles. I see that you need to vent your frustration, so I'll be happy to sympathise even though I envy your problem." but the fact is as humans we're just as likely to think and say "you think you've got problems?"
Don't feel guilty for your joys and successes, but understand why some people are unable to share them. You can always find the right audience to appreciate your needs at the time, whether it be venting or celebrating. You can't vent, brag, or celebrate everything to everyone, but you can always find someone appropriate for each situation and topic.
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