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Extroverts and Introverts of Reddit I NEED YOUR HELP! My F [35F] friend K [35F] looks miserable whenever we go out. It seems to be getting worse, so ......

Habika

Oct. 10, 2019

Tl;dr My friend looks miserable when she's really having a great time. I ask her if she is REALLY ok/ bring it up too much and I have hurt her feelings a lot. I want to be better.
I am F; she is K. I feel like a/ am a busybody at this point. We've been friends for over 20 years. In her 20s she'd been through a lot, and she started to look uncomfortable when we'd go out. It got the point where if we were with a group the other people would ask me if she was ok.
I figured it was social anxiety. I try to make home plans for our get togethers, but often she invites me for our outings--so I KNOW she wants to be out and has picked where we're going. She's introverted and sensitive in that she's intuitive and highly attuned to people and situations, so people don't like to make her feel self-conscious. She doesn't have many other friends; she feels like nobody likes her. She's expressed that she's a little upset that she doesn't get repeat invites or second dates. I'm concerned it's partly due to her facial expressions. It's getting worse. To give an example: if I ask her if a belt goes with a dress she winces and then says "yeah it looks good!" She's a genuine person; she means it looks good. If she's in a conversation she grimaces--even if she's talking about something she enjoys!
RBF doesn't cover it. Impassive doesn't cover it. We went out for supper at a fun funky place with food she liked and our server was truly concerned for her welfare. I don't blame her--she was trying to figure out if K was dealing with a ruptured appendix or if I was holding her hostage. I asked K if she was ok and if she was having a good time.
That upset her, and I'm starting to get a feeling as to why. She gets that question a lot. And it immediately calls attention to the fact that whatever it is she's SUPPOSED to be doing to show she's having fun isn't happening right now to her companion's standards. So by asking that question I made her feel like she's supposed to put on this fake performance and jump through all these hoops just to get some food. She doesn't want to talk to me right now because I'm just one more person who asks her that question and ruins a night out.
She's a wonderful person. I want to be a good friend. I tried to explain that her facial expression was such that I felt I had to ask or I would be being a negligent friend. When other people ask me if she's having a good time when she's giving all traditional external signs she isn't I had been saying "yeah, she's having a great time" and I'd get looks of disbelief. More recently I've said "yeah, that's just K." She heard about that and got mad that I was "dismissive." She says she is fine and to leave her alone about it.
I'm also having trouble because it's so embarrassing to be out with someone who looks so miserable. I'm worried that I'm not being fun enough for her, but also it puts more attention on me.
My Mom is lovely, but she loves to call attention to herself in odd ways. That has resulted since childhood of people looking at me to see how I'm reacting or coming to me with "what is up with your mom?" It seems small but it is absolutely triggering and I hate it. K KNOWS this.
I've been through some rough stuff and I should just be grateful I have a friend. Then we try to go out and it all starts again. :( I have a history that I am working on of thinking I'm being nice and coming across as abrasive. I don't want to hurt my friend (anymore).
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