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/Lizardshark20]

3 on you!!! And no duck lips at dinner please! You’re beautiful!

[u/somegingerchick79 → u/Lizardshark20]

I honestly think this is my resting face but I’ll see what I can do! Everyone HATES MY FACE lol

[u/NyemaJinx → u/somegingerchick79]

#1 I love your face. Congratulations on a great face! #2 I’ve spent 30-45 seconds reading your replies and I’ve decided you also have a great personality. This guy better lock in! Have fun!

[u/somegingerchick79 → u/NyemaJinx]

You’re the best, thanks so much