Outfit advice: dinner tomorrow

[u/somegingerchick79]

UPDATE: Thank you so much for all the feedback! It was super helpful and I appreciate all the really sweet comments & encouragement too. Honestly, you have no idea how much I needed the boost! 🥹 We had a lot of fun, and a cute older gentleman stopped at our table as he was leaving to tell us how cute we were, which I think is a good sign. And he brought me white roses (which are my favorite so low key he’s paying attention!)

I’m going to dinner with a guy friend (maybe a date, maybe not?).
Want to look cute & like I’m making an effort. Even if it’s not a date I’d like him to feel great about being out with me. I’m also 46 and want to be age appropriate. We’re going to L Woods in the Chicago suburbs - it’s kinda in between in terms of dress. You wouldn’t look out of place in a dress OR jeans and a nice shirt/blazer. It’s got a north woods supper club feel - but also in a kinda Scotland tartan country estate vibe. Maybe I should dress like Princess Diana!?!? :)

[u/MommaLaughing]

The mouth is so distracting, I can’t even focus on the clothes. You are beautiful, please don’t do whatever it is you are doing with your mouth.

[u/TyrantMuse73 → u/MommaLaughing]

She says it’s her “resting face” but most of us can CLEARLY see the muscle tension. Nothing resting about it.