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How do I show him that I care?

I've been friends with this guy for over a year now, and he's great. However, he always downgrades himself and it sucks. Him and I never really have serious conversations about how he feels because our friendship is pretty much just banter and teasing each other, but he says things that people hear and know he is not necessarily okay. I ask him what's wrong, but he doesn't say much, he just says he'll be fine. This has happened multiple times.

I've told him that I care, but he kinda just brushes it off. I don't think he's the best with showing those sorts of feelings. He's such a great guy and I really look up to him, and seeing him upset makes me upset. What should I do to show him that I really do care, even if we don't talk about that stuff? He has opened up to me about some stuff, but then he shuts me out about other stuff but I still hear about it from others.
He's only going to understand his worth with time and compassion... What you are doing is great but that doesn't necessarily mean he's going to be okay anytime soon.
All you can do is be his friend
SW-User
This brings back so many memories.

I had a friend like this. She was apparantly ready for love (especially with me) but I had no clue. I just thought this super nice girl was just super duper nice to me.

We dated at the wrong time later on. A very short relationship. We are still friends today and this is how I know about the previous years where she liked me. (We re-hash things a lot)

The problem is... by the time you tell him the right way... it’s not going to be the right time. It will be awkward.

I say do it this Christmas. Get him something simple. Homemade? Cookies?

Write him a note. Do it on a back of a printed love poem. Or something.

This is always a good one:

 
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