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21 y/o woman - masculine dress style- never had a date/been kissed

I've never had a guy interested in me. I have a more masculine (wear guys jeans, ball caps, button down shirts when going out/dressing up, don't wear dresses, skirts, makeup, etc) style of dress and am a college athlete....
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Do you prefer to date someone that compliments the way they dress?

If you dressed in high heels, dresses, or business attire would you date a guy that wears mostly t-shirts, sneakers, and jeans. Guys if you dressed mostly in business attire or casual/professional attire would you date a...
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I need some help on a date outfit?

Okay, now that we've settled it will in fact be a date ;) what do I wear? So, this'll be our first date (my first date ever, and I'm 20), and only the second time we'll see each other face-to-face (we live an hour or 2...
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What to wear on coffee date?

First date going for coffee after work. What do I wear? Dark skinny jeans tucked into black suede wedge boots? A mid thigh black skirt with boots? Or do I stay in my work clothes? (blouse, tucked in pencil skirt right...
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GUYS - Do you get sick of seeing women wear jeans all the time?

So everyone seems to wear jeans all the time now. What do you like to see women wear when you're just hanging out, going on a date or something? (Outside of slut wear.)
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What should I wear tomorrow?

My boyfriend and I are going on a date. We were thinking about going to get a bite to eat and watch a movie afterward. I always look crap every time we go out and he looks way better then me. I don't wanna over do it but...
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Wear this on your first date with him?

Ladies I'm just curios so I know what not to wear when I do put myself out there dating again and yes I'm being prepare for any situations so just bear with me OK thanks and please honest with me. If a guy you are dating...
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Should I "dress up" even if she winds up not to?

I'm going to a Christmas party on the 2nd. I know, kind of early, but that's when they can do it. So, I kind of have a "date". I offered her a ride, but ever since then she's sort of acted like it's a date, asking me if I...
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What to wear on first date?

I have my first date with this guy tomorrow and I have no clue what to wear... I'm thinking either a cute dress and cardigan or skinny jeans with a cute top and maybe a scarf. Either way I am wearing flats. Heels are...
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I have my first date with this guy tomorrow and I have no clue what to wear... I'm thinking either a cute dress and cardigan or skinny jeans with a cute top and maybe a scarf. Either way I am wearing flats. Heels are just too much for a first date. What do you think?
Dress with cardigan
Skinny jeans and pretty top
Select gender and age to cast your vote:
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First date clothes?

Men what would you prefer a woman to wear on the first date- a simple casual dress or jeans and a nice top Our date is at 6 and meeting at the zoo Usually day means casual and night means fancy- but what ever I wear has...
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Do guys care what a girl wears during school?

To be honest, I am a jeans, sneakers, and sweatshirt kind of girl. I can pull off the more dressy look, but most days I want to wear something comfortable. I also do not wear makeup simply because I want to let people see...
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So here is my second date plan, any suggestions for improvement?

I have known this girl for couple of weeks and I asked her out and it was a decent success. I called it "hanging out" though. Last Friday, I first took her to a coffee shop she suggested, then we went swing dancing, and...
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If a girl you dated wore midrise jeans

Okay, silly question. Say a girl you were dating or liked wore midrise jeans, would it be a turn off? Midrise jeans are less a fashion statement, but they are jeans that come up a bit under the belly button, and sit...
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What to wear on first date?

So I have a first date coming up and I'm deciding what to wear. Its a warm summer night so should I wear a summer dress, or a nice shirt and jeans or something different?
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My first date outfit!?

Ok, I've been told I have a square wardrobe. In the summer I wear jeans and t-shirts. In winter, some long sleeves and sweaters over the tees. Add some sneakers, there you go. Now for a date, I put on dress shoes rather...
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First date guys style. What to wear on a first date?

So Ladies this is a tricky one if I take out girl on our first date what do I wear? 1) Golf shirt, Jean, All Star Shoes 2) Button Shirt, Jean, Formal Shoes 3) Button Shirt, Jean, All Star Shoes 4) T-Shirt, Jean, All...
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What should I wear at the first date?

my boyfriend is far away...but he's coming this summer! THANK GOD! And we will go out...first date! and I have nooo idea what to wear...im really nervous...and I need your help! I don't know should I dress cusual? like...
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Do any other girls have nice jeans and casual jeans?

i have a few pairs of nice jeans. I paid a little more for them, they're tighter, and fit me nicely. I wear them to school, on dates, and when I go special places. then I have a few pairs of casual jeans that were less...
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What to wear on my first date with this guy I really like?

We're going to the movies, and its our first real date. We hung out before with other people but not alone. I have no idea, what to wear? I'm thinking really cute jeans.. but I don't know what kind of top? what shoes?
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2nd date tonight. What to wear?

We work together and are going out after work. I'm not going to change to go out so I need to go to work in the outfit we're going out in. It's a volunteer thing today. I need to be able to move so a dress it probably out...
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