Impress with your Dress!

Winters in Chicago are cold. There's no surprise there, but what does raise my eyebrow is how little some people wear during the bitter months. This was my dilemma a few short months ago when I had my first date (!) in over a decade: What to wear?



I answered this question as I thought my best friend, Laure might: "Impress with your dress!" Is this an out dated concept, impressing with your dress? If not, what does it really mean? To me it sounds less like wearing my Sunday best and more like wearing next to nothing in frigid temps based on the scantily clad running around the city. Open to dating, but not frigid temps, I modified it in my mind to mean wearing something flattering to my figure while highlighting my best assets. But I'm getting ahead of myself…so I had my first date.



How, you might ask, did I secure said date so quickly after deciding that I would date again? Two words: Internet dating, which I will savor during a later column when I have more time to discuss it with you at length. Anyhow, I met with Alec Brownless*, a New Yorker and sometimes Ohio dweller. (If one dwells in Ohio…) Alec flew in to Chicago from Cincinnati to meet me (plus). He booked a hotel room near the airport (plus) and allowed me to make the dinner reservations (and another plus! So far so good, right?) He held all doors for me (nice) and didn't backseat drive (perfect!) The conversation flowed without awkward pauses.



I was dressed from head to toe, covering just about every inch of me…even the good parts! But I had my eyes, hair, and wrists (oddly, a turn-on for some) to work with. WHAT I wore: Long black coatdress, sleeves rolled up (and hence the wrists), long black leather boots, black tights. I will say that I stayed warm, and I was impressed with that. WHERE I wore it: Dave's Café, WHO I saw: Alec Brownless, HOW late I arrived: twenty minutes, BUT his plane was late so technically I was on time. WHY I'd go back: the food was well prepared and felt homemade especially for me. Will I see Alec again? I'm not sure. There were a few minuses that you may be able to help me with. He spoke of his ex-wife—a lot and not in a negative way. He appeared very "I'm man…you're woman and you have your place several steps behind me…" an exaggeration, but a feeling I got about him nonetheless. While we didn't argue, all the signs were there that we were on our best behavior, but could easily fall prey to the petty argument (I booked the reservations under my name and his eyebrow went up at this), he challenged me about my knowledge of one of my favorite movies, 'The Usual Suspects' to which my eyebrow raised, and he didn't go in for a goodnight kiss (?) So there were a few warning signs. I want to know your thoughts: Should Mr. Brownless be granted another shot at greatness or was his behavior unseasonably cold?