Guys, what would you prefer to see a girl wearing if you hadn't seen her in awhile?

I am going back home to see a man I haven't seen in a year and would like to continue flirting with him, but hopefully it will go further. He hasn't seen me since I've lost 30 pounds. When I saw him last it was spring and I was wearing a brightly-colored belted sundress that he overtly praised.

Now that I'm in law school, I own more pencil skirts, suits, things of that nature. I can't decide on trying to look sleek and professional or pulling out another fresh dress. (Both accentuate my figure equally well and I am comfortable in both.) Men, would you prefer to see a woman dressed in a skirt suit or a sundress? Any other ideas?

Updates:
I should also add: He's much older than me, and he's around people in business casual and business attire all day. So I don't know if I should dress in the pencil skirt/button down in order to present myself as a sleek, put-together professional, or if I should put on something that makes me seem like a "breath of fresh air" in his work environment.


Also, as I said before, both looks show off my figure equally well. I'm not talking about wearing a shapeless sundress, it would be fitted.

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Most Helpful Guy

  • I say thanks for the update... It helps.

    Go breath of fresh air all the way. Skirt suit can look nice but his brain is on overload if he sees it every day. I think the dress will have more of an impact especially if you know he already likes you in them anyway.

    Don't get me wrong, I think the business attire lawyer in glasses letting the hair down in her office is a very very sexy scenario. Skirt suits can look very nice.

    This is a different deal. He will love the "new scenery" and especially your new shape you have worked hard on. Time to shine dear.

    Best of luck.

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What Guys Said 8

  • Sundress. All the way. He has praised it before, and it'll show you care about his opinion. Also casual over professional when trying to flirt, unless you are meeting him through a professional medium, which I assume you aren't.

    Also congratulations on the weight loss. 30 lbs isn't easy to shed.

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  • If that'd be a situation for me, rather than looking at your dress I'd be noticing the way you'd look at me, your smile, hair and then your figure. I don't think the 'kind of dress' is important, just wear that'll show up your curves better. Best of luck.

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  • Pants and clean white underwear so I could give her a wedgie.

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  • man do I f***ing love sloots in sun dresses.

    ps. go commando co when that wind picks up = bonus reps

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  • There's nothing hotter than a girl that's put together well.. With that said, both a sundress or more sleek look can be hot- but a sundress is going to be more on the casual side and probably won't show your figure off like a pencil skirt. I'm gonna say go with the sleek look, he's seen the sundress.. I'm a sucker for a girl who looks smart and hot at the same time!

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  • First off congratulations on the weight loss. I'm currently trying to drop weight for my own health and to help with girls. Go with sundress.

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  • Just wear whatever...however, if I were meeting a woman for flirting or whatever I wouldn't want to feel like I was in an interview with her

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    • Status update: When Kelly Bundy wanted that South American guy, she thought he wanted her to look like a South American girl. He spent 7000 to get away from that scene. He liked Kelly, for Kelly.

  • I'd like to see her wearing a white shirt and the black pants!

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What Girls Said 3

  • You should go with the professional look. It will be something new. He will both see your new figure and your new way of being.

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  • business casual is boring unless you are in an office or going to work. Wear a nice fitted dress that shows off your figure but is also vibrant

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  • i think you should wear a fun flirty summer dress ;-) I think men love that

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