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Dating Triumphs and Tragedies
by Nicole Roberge

Dressing to Date

“I have to tell you,” the lady at the post office said with a little laugh, “that I bought almost the exact same outfit for my three year old granddaughter.


I was back home for Thanksgiving and running some errands. It was all about comfort, and I had on a top with flowers on it, and jean overall minidress. I thought, trendy. She thought, toddler.

“But,” she continued, “it looks just as adorable on an adult as it does on a little girl.”

That was very sweet, and to tell you the truth, I took it as a compliment. I was comfortable and I didn’t care if I looked like a little kid.


You know that clichéd phone question… “So, what are you wearing?” Well, the answer does make a difference. Maybe that’s sort of a tongue in cheek phrase but still.

Right now, for instance, I’m wearing jeans, a long sleeve shirt, and fuzzy slippers. (I’m home in Connecticut, and it’s cold). Clearly, if I were going out with Mr. Studly, I’d toss on something a little snazzier. I might keep on the slippers though.

But the truth is, we dress to impress, and our apparel choices are dependent upon who we are dating. And generally, as time goes by, he will eventually see the real us. Whether she is the girl who lives in her grey sweatpants, the one who really does sleep with makeup on, or the small-town girl who retreats back into her overalls the second she gets home. And by that point, he has usually come to accept us as we are, and (hopefully) love us for who we are. But if we showed up as our “normal” selves on a first date, would he be so keen to ask for a second? First impressions do count, and if I showed up with that disheveled, yet oh-so-sexy, sloppy ponytail on the side of my head, chances are, we wouldn’t quite make it through our appetizer.

So when we’re meeting our potential love interest, especially a blind date or online match, what do we think about when getting dressed? Because we do think about it. And also, what unconscious things are triggered between dating and dressing?

1) Location — There is the obvious standard of where the date is taking place. If you are meeting in a coffee shop or swanky restaurant, or perhaps a bar or the movies. Outfits can vary from tank top, jeans and heels to cute skirt and flats to the little black dress.

2) The guy — Is he a Business Man, Hands On, or Mr. Teacher? What he does for a career can make you want to present yourself differently. If he is a lawyer, you may want to seem more professional and mature, even if you were just throwing back shots til 3 am the night before. Whereas if he’s a bartender, you might dress a little more wild and carefree. But don’t let a guy’s job fool you. Remember, it’s his job, it’s not who he is. He might be happy to be going on a date and getting away from his work. If you go out and try to mimic his profession, it could be a turn off. Don’t dress to impress, dress like yourself. It’ll make him interested in the interesting person that you are.

3) Season — This can be tricky, especially in cold climates during winter when there is the potential for snow. How attractive can a big fluffy pink snowsuit be? Yes, they’ve tried to make sweaters low-cut and boots be a little stylish, but still, it’s hard to feel sexy in layers. Here is where the subconscious thing comes in. Many ladies know that once they get inside to their date location, it will be heated, so they can wear something a little more flashy for the actual date. But for the arrival, they can layer up with a cute sweater and heavy coat. So they maintain their fashion sense, but know that warmth, and avoiding hypothermia, is of importance as well.

Yes, he will notice what you’re wearing, but more than that, he’ll notice how you look. Years down the road, on your golden wedding anniversary, when you’re blabbing about those first moments of meeting and the song you heard in the background and how his tie was crooked and then you wait patiently for him to recount every detail of the gorgeous blue hues of your dress, he won’t say a word. Instead, he’ll smile, because he’ll be speechless thinking of how stunning you looked, and how he knew then that you would make it to your golden wedding anniversary. That’s the kind of impression you want to make. So who cares if your lip-gloss matches your heels. Put on a smile and go get your guy.

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

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