What should I wear?

I'm a chunky guy and tomorrow I'm asking this girl out that I like. I dress in a few different ways when I go to school. I always wear a hat, either my Yankees hat, (non flat brim, I'm fat and white) or my Hurley hat.

A. Overslept- shorts, flip flops, hoodie

B. Clean- Polo or buttoned down shirt, khakis or jeans and some nicer sneakers

C. Gearhead- Tshirt, slightly stained jeans, dirty Nikes

D. Average- Clean T shirt and jeans or shorts with nicer sneakers

I think if I go for my clean look I'll look like I'm trying to hard. I know 2 of my looks don't get any girls, but they serve different purposes. What do you think I should wear?

Also- I like my flip flops a lot. How do girls feel about the mandals?

Updates:
Well the Rangers lost last night so I'm also going to have to shave my playoff beard.
I ended up wearing a nice buttoned down long sleeve collared shirt, yellow with blue plaid and some nice khaki shorts and flip flops. it didn't matter though mainly because I bitched out.
Well I didn't need the weekend to mentally prep. Everybody told me to give her a call so that's what I did. I asked her if she wanted to hang out tomorrow but she had to work, so were going out mini golfing friday night.

Tomorrow night is our first date

What should I wear?

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Most Helpful Girl

  • I love mandals (I never heard that term but it's funny). But I personally like the average look. I am preppy so the clean look is less attractive to me because opposites attract for me. But which one makes you look more slender. If you think she likes chubby guys (because I do) then the question is irrelevant. If she doesn't then try to make yourself look more slim. I hope I didn't offend you.

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    • Not offended at all. A button down shirt makes me look pretty slender. I'm not sure if she likes chubby guys, I'm hoping she does though

      How have you never heard mandals? I lived in 2 states and I knew it in both. haha

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    • You don't have to respond but you remind me of this guy I like. He is white and chubby and your responses sounds just like him. Hope I didn't creep you out.

    • I get that a lot, everywhere I go, somebody another chunky white kid that's funny as all hell

      that's at least what I hear

      I don't even think I'm funny but everybody thinks it's hilarious when I'm a smartass or that I say half the stuff I do

What Girls Said 9

  • you could mix and match.. I reckon the polo with shorts and flip flops..if that's less try hardish.. although otherwise I would have just said option B. clean. either way good luck! :)

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    • That is very true. It's supposed to cool off tomorrow so I'm thinking the mandals are out.

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    • My humor turns awkward when I'm nervous. I'll make the weirdest joke and then try and play it off but the damage has been done. But if I'm not nervous I can think of something stupid to say in a fraction of a second.

    • Lol then I would avoid it unless it comes naturally. don't worry what's the worst that can happen? its never as bad as it seems.

  • something similar.. what you picked out last time seemed good. don't worry about it too much.. she obviously must like you enough to say yes!

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  • Why did you bitch out? You sounded like you had confidence. Try again tomorrow. Don't think to hard about it, just do it.

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  • YAY! congratulations! haha no need to worry about an outfit either.

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  • oh no! its ok try again another day.. just make sure you feel like it :)

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    • I was going to try again yesterday, but I overslept until lunchtime and then went in. I only have morning classes with her so I was kicking myself in the ass all day.

    • Aww.. its ok you have the weekend to mentally prep yourself now. let us know how it goes!

  • this is what should wear ah plaid shirt

    some cargos

    and so mid socks

    and some nike blazers

    now that's the perfect fit

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  • t-shirt or polo, khakis, and mandals

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  • Congrats!

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  • I think B. The shirt with jeans. What colour shirt? Do you have to wear the hat? What's your hair like?

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    • I have real short hair. It's so short you can see my scalp. I like it that way. And I'm normally clean shaven unless it's playoff season for one of the sports I like. Then I have a playoff beard, although I'm considering growing out my chin.

    • If you like it that way, maybe you could try without the hat? Might look tidier.

      Though if you feel more comfortable with it, that's cool too

What Guys Said 0

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