Don’t wear something because you think your date may like it especially if you feel uncomfortable in it! I’m a heels girl so I always wear heels when I go to casual dinner and movie dates, but flats are totally appropriate to wear. Go to one of those Indian restaurants with a million Christmas lights hanging from the ceiling.
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You might think about how you should act, if the conversation will flow, if you should play hard to get, or if you guys will kiss at the end of the night.
I love a fashionable guy, but I hate when someone dresses so overdone that they end up looking more of a hot mess than fashionable. For example if you guys decide to do a picnic in the park opt for a cute and comfortable pair of shoes instead of six-inch heels. Never over-think it because when you do, the outfit ideas may not flow as freely and you may end up looking crazy—and we don’t want that to happen! Pull out that freakum dress that you save for special occasions and rock the heck out of it. Remember to keep your footwear comfortable as you may be doing a lot walking to find the perfect rest spot!

If you feel that your outfit is too overdone for the place that you are going to…chances are it is!
Your California Privacy Rights The material on this site may not be reproduced, distributed, transmitted, cached or otherwise used, except with the prior written permission of Condé Nast. Among all the things that make you nervous about your first date with someone, picking the perfect outfit should not be one of them!
Please don’t get freakum dress confused with hoochie mama dress—if you can wear it to the club, chances are its not fancy restaurant appropriate.
Converses are my favorite type of kicks, so if I want to wear sneakers on a picnic date, I usually wear those.
Since you will be going on rides stay away from dresses—you don’t want your goods all on display. Cherrie's blog is all about being fashionable on without breaking the bank, hence the title "Making the Inexpensive Look Expensive"!She is currently finishing up her Masters degree in Nutrition and is from Brooklyn, NY. When I’m feeling myself, I throw on comfortable pair of wedges that give me stability while walking on the grass in the park. If its chilly, you can wear leggings and an oversized sweater with some riding boots, jeans and a comfortable top, or you can even wear tights and throw a pair of shorts over them for a rugged look. When you get there, take in the view and worry that this whole plan was way too romantic for a first date. Picnic dates are usually for the warmer months so you don’t have to worry too much about staying warm, but if you do happen to go on a picnic date during a colder month, wear a denim jacket, boots, and leggings for warmth!

You can definitely wear a pair of slacks, but that might have you looking more professional rather than first date appropriate. Allow the visitors to approach you one at a time and attempt to engage in small talk about work while you subtly hint that you’re on a date and want to be left alone.
You are allowed to do absolutely anything inside this bag, but you choose to talk about how many siblings you both have.
After you both stand there for five minutes without catching the bartender’s attention, start waving around a ten-dollar bill while miming drinking.
Show this trash man to your date and tell him that it represents every boy you have ever dated or, honestly, every boy you have ever met. See how long it takes your date to stop talking about a funny Tumblr and to realize that you want him or her to kiss you. Go for a walk along the river and discuss how much you hate James Franco with your date, James Franco. Every time one of you suggests a time that the other can’t do, cut a little piece of your clothes off.

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