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Online Dating Magazine > Columns > Dating Triumphs & Tragedies > Dressed to Impress

Dating Triumphs and Tragedies
by Nicole Roberge

Dressed to Impress

I was about to go on a date and had a red dress on when a friend who was over took one look at me and goes, “whoa, hot date?”
I jokingly replied, “I’ll know when I get there.”
I then reassessed myself in the mirror and realized, not because of what he said, that I simply didn’t really like or feel comfortable in the dress I was wearing.

Next, I tried on a long white, summer dress, which I liked, but the straps seemed kind of itchy, and that might be a bad first impression if I were itching my shoulders the whole time.  Time to try on something new.


I finally settled on a white and yellow flowered v-neck dress, with ruffles around the edges.  Hard to explain, but it was pretty and flowy and comfortable.  It even had pockets.  Third time’s the charm!

I realized that I probably could have gone with the first dress, but I had to try my options out.  After all, this was a first date, and ultimately, I was happy with the dress I settled on.  It was perfect for a summer evening dinner date and was both pretty and comfortable.

Then I realized that I had to try on three dresses to get to that point and I wondered, how many outfits was my date going to try on before he found “the one?”  Do guys go through the same dressing drama that girls go through?  They might.  I had friends in college who lived in the apartment across from me that would come over and ask if their outfit was okay for a date, and after us girls approved it, they were satisfied.  I even have a friend now, who I don’t live real close too, but who will text message me with what he plans to wear on a date and ask if it is okay.  If I say yes, he wears it.  Guys tend to like other girl’s opinions when he comes to dressing for a date, because after all, another girl is who they are going to meet.  But in my case, I had to go by trial and error, hoping I could find the perfect dress for my date.

I think that, from what I’ve noticed, people have their usual standards of dressing when it comes to dating.  For me, if it is warm out, I will wear a sundress—a) because I like them, b) because they are pretty, and c) because they are comfortable.  When you go on a date with someone, I think that should be the standard of how you assess your outfit.  What you like, what you think looks good, and what is comfortable.  You don’t want to dress in something that you normally wouldn’t and be uncomfortable just because you think it will impress the guy.  You might just end up sitting there the whole time wondering why you wore that outfit instead of concentrating on the date.  It’s best to be yourself because if you get to that second date, you’re going to want to wear something that is “you.”  And if you project a different image of yourself on a first date, then you’ll have to do that again, and that can be hard to keep up with.

I don’t want to say guys have it easier, but most guys that I have gone out with usually stick with jeans or khakis and a polo shirt.  Something casual that will work in a low-key or nice restaurant.  Then again, girls have more options.  They don’t have to wear a dress (that’s just my preference), they can wear jeans and a nice top, or a skirt, or khakis, capris…wow, there are a lot of different clothes for females.  So does that make it easier, or does it make the choice harder?  I say it just makes for a lot of trying on multiple items of clothes until you hit the right outfit.

Of course, it all depends on where the date is at too, but let’s not think too hard about it.  Dressing for a date can seem daunting, but in the end, it’s not about what you wear, it’s about who you are, and that will shine through more than the dress you are wearing.  Be comfortable in what you’re wearing and be comfortable with yourself, and the rest should be easy.  Hopefully. :-)


Dating Triumphs and Tragedies is published every Sunday by Online Dating Magazine columnist Nicole Roberge. She can be reached at

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