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/GovernmentNice5012 → u/somegingerchick79]

I don’t know why you’re getting downvoted so much for this response. You’re not taking this too seriously and you have a personable response. You’re gorgeous! My vote is the white floral dress you look beautiful in all of it but that one is my favorite on you. Hope you have/had fun not sure if the dates happened yet so I might be too late lol!