Girls/ Have you ever dressed really cute only for your date to show up INSANELY under dressed? How did you react when you saw him?

Guys - (so you don't feel left out) have you ever been overdressed and your date looked like she just rolled out of bed?


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Most Helpful Guy

  • I once was at my old work... and this really gorgeous looking girl walked in, dolled up to the nines, my god, she couldn't have looked any better... her date, I'm assuming, walked in with sweatpants and a sweatshirt on. Now, I don't know if they were actually on a date or not butttttt if a girl goes all out for you like that, and you're wearing sweats, I would think she should get a new man... because, that's not very cool. I'm not saying you need to go tux, but at least something other than sweats. Had I not been an employee there, I probably would have said something

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    • YES!!! YES!! A million times yes to this response! Thank your Mr Anonymous man!!

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    • I'm glad! Thanks for an insightful response.

    • So, have you ever done this... where you've gotten all dolled up and then saw how he dressed up?

What Guys Said 6

  • the opposite. I was picking this girl up and it was hot as fuck! so I wore my sporty clothes, shorts dri-fit shirt and a hat. regardless of the heat she decided to fucking put on one of those dresses, but its kinda like a mini dress sort of and makeup and did her hair and everything :/ don't forget some jewelry hahaa. wasn't awkward for me but I don't know how she felt about it lol.

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  • In high school, perhaps, but it was more i guess she had a pretty preppy style and turned it up somewhat, and I was... not a prep. So both of us were just looking even more into our own styles than usual

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  • Yeah that has happened. I normally dress in a jeans/sport coat getup, and when we met up, she was dressed entirely casual--I guess her previous dates weren't impressively dressed, so she went casual expecting I'd do the same, lol. It was a fine date though. I like to keep them low key anyway, so I took her for a coffee and a walk in the city commons so nothing would feel out of place.

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    • did she ever dress up more as you continued to date?

    • Yeah, she dressed better for the next few dates; honestly, it isn't the biggest deal to me, although I do appreciate it when a girl is dressed nice. Not a deal breaker, but a definite plus.

    • I understand. Well said.

  • I remember one date was just to go to the movies... so I turned up in a button up shirt and jeans, she was in a beautiful blue knee-length dress. I felt like a slob!

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    • I would have no problem with that look as long as your shirt was ironed and you had on good shoes!
      Was this a first date?

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    • Converse or DC's aren't really my thing but if she had a cute figure, Im sure she looked just fine.

    • She looked fiiiiiiiiine no matter what she was or wasn't wearing ;)

  • It's always best to dress in smart casual wear. Not too formal and not too informal.

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    • Thanks but asking for specific experiences not generalizations. :))
      appreciate the thought tho.

    • I'll respond how i wish.

  • I turned up to pick her up and she was wearing nothing... I was shocked, but you know, fine with it. =D

    Have heard of this, it's a bit worrying, maybe a miscommunication.. if you like them, you run with it I guess, and try to coordinate next time. If you're not that into them, then the date ends there.

    Could you help me with a question pls?

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What Girls Said 8

  • Yes!! I felt very stupid. It was probably my fault though. I was wearing a lace top, bodycon skirt and low stilettos. And he wore a wrinkled t-shirt, shorts, and flip flops!!! I felt like a dumb. And I felt like he didn't see the date as important as I did.

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    • Girl... I see nothing wrong with what you wore. NOTHING!! I would feel the exact same way!! Did you go out with him again?

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    • At a restaurant we both had never been to for a lunch.

    • I just lose my shit if a guy wears flip flops on a date. Just my opinion though.

  • Haha yes. I felt stupid and wanted to go home. But then we had one of the best dates ever. The looks we got from other people though -.-

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    • Awww!! yah!! but what were you wearing and what was he wearing?

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    • lol I wasn't crying, but I was definitely laughing a lot whenever I saw his shoes trying hard to not shake my head too.. at first we were sitting at a pond next to each other, so I had a lot opportunities to look at his sandals and/or white socks.. and I looked a lot at the floor because I was shy xD

    • I would have contemplated throwing him in the pond to give him a reason to change his clothes!!

  • Yup! Many times. Just last week actually. I wore a really cute dress and my makeup and hair were on point and he showed up in jeans and a t shirt lol. I didn't think of it but he was like "wow that's some dress I feel like a slob"

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  • No, other way around for me! I was underdressed (wearing a casual t-shirt and pants) and he was in a suit LOL. So awkward.

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  • Never happened to me before, but I don't wear skirts or heels so I'm never really overdressed.

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  • I blush... then try to look past it.

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  • Hasn't happened to me before. I avoid getting all dressed up so situations like that don't happen.

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  • Yes! I was like, lets just go to the pub instead of dinner. You can nevr be overdressed for a date.

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