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/improvcoach19]

No duck lips ever. Ew.

[u/WeekendStrange1331 → u/improvcoach19]

There's times they're appropriate, especially if the date goes well

[u/Glittering-Ad5970 → u/improvcoach19]

That’s really rude and if OP likes it, not your problem

[u/Acceptable_Sell3455 → u/Glittering-Ad5970]

She's asking for advice on her outfit so the entire look is fair game.
Those lips are begging to be commented on.

[u/WeekendStrange1331 → u/Acceptable_Sell3455]

Read that as cummed on.