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Feb 9, 2012 >> My Funny Valentine: Chicago Tastemakers sound off about their most memorably silly V-Day

We’re asking some of the most lovable Chicagoans to weigh in on some of their most memorable V-day moments—the good, the bad and the ugly!

Founder, Haute Closet & Founder, Dose Market

2nd grade Valentine’s Day—I will never forget. It was, perhaps, my styling debut: I plotted my outfit (oversized red-shirt, t-shirt half-tucked into a black & white check miniskirt with all of the coordinating accoutrements) for weeks to coordinate exactly with the box I decorated for collecting Valentines from classmates. I’m sure the outfit wasn’t the reason, but that year I netted my first real Valentine: Drew from the third grade. He presented me with a heart-shaped box of chocolates with a hand-illustrated card that read: “You’re the pot of gold at the end of my rainbow.” Swoon-time.

Founder, Suitor

I was in college, totally broke and living in a weird hippie co-op. All of my friends had a Valentine and I was determined to not feel sorry for myself and to make my night “special” by watching a romantic comedy and buying myself a box of chocolates. I rented a $.99 special at the video store and having no idea how expensive a box of chocolates were, ended up with a few generic peppermint patties. I came home for my “special night” only to find my co-op mate watching a documentary on the evils of chicken farms with his “Valentine” on the only TV in the house. I ate my peppermints alone in my room and listened to The Theme from Mahogany by Diana Ross over and over again on my record player. Dramatic. That next summer I met my beau and been madly in love everyday since.

Creative Director & Co-owner, Epoch Floral

Last Valentine’s Day will be a day that will be permanently foil wrapped, dipped in chocolate and arrowed in my mind.  After a long day of work designing flowers and love note writing, I headed home to get ready for a romantic evening: a second date. Because it was a second date and I had no expectations even though it was Valentine’s day, I wasn’t nervous.

I arrived promptly at 8:00pm.  I came hungry and clean with a homemade Valentine in my hand, a bottle of wine and a smile. He greeted me at the door with a handful of roses and a bib. A Bib?! He explained that he put together a dinner of red: he made crab legs.   Lucky for him, I love crab legs so the bib suddenly became endearing and thoughtful. Once inside the apartment,  he said he had a surprise in the dining room. We turned the corner into a candlelit room and to my surprise, there were two other people already seated.  Yep, it would be a great night for me to meet his parents. A second date, on Valentine’s Day, with parents and crab legs.  As I answered “How did you meet?” and “What do you do for a living?” with butter running down my chin I thought to myself: I wish I had brought more wine. I will never forget this evening.  It was filled with surprises and expectations and a whole bunch of crab legs.  Needless to say, there wasn’t a third date.  In fact, I haven’t had crab since.

Public Relations Coordinator, 900 N. Michigan

I was all of 22 years old, living in the northern suburbs and working at Joe’s Crab Shack at the time. I had a full-on Mohawk and blonde tips. Since the gay male dating pool in Gurnee was a bit dry, I decided to take matters into my own hands and ‘propose’ to my best girlfriend who worked as a bartender at the time. I walked in around 2.00pm with a hand written poem in my pocket and a cheap ring from Gurnee Mills (The mall in my hometown). I walked right into the bar she was working at and got down on one knee.  She came around from the bar, a bit confused as to what was going on, as were the patrons. I began to read the poem I had written—something incredibly cheesy with simple rhymes (best friend in my life, won’t you be my wife, etc.) and pulled out the ring.  She was already tearing up at this point and screaming out “Yes!”, before I could get up from my kneeling stance.  Before I knew it, the whole bar was clapping wildly and I was as red as the grenadine.  To this day I wonder what those patrons must have been thinking when the gay guy with a Mohawk proposed to the hot chick behind the bar.  Either way—it’s a story I’ll never forget, we’re still ‘married’, and I’m pretty sure In-Laws will never be the same.

Senior Marketing Director, Skoog Productions

My fondest memory of Valentine’s day was in fifth grade when I had more admirers than I have ever had. I remember getting eight gifts—from EIGHT different boys! This was of course pre-braces & puberty, so it was probably the last time that I had that experience. I really have not had any bad Valentines Day experiences I suppose. Even when I was single, I always had a blast going out with my girlfriends. If I was single right now, I’d for sure be hitting up Bull and Bear for their Girl’s Night Out Sex and the City game night! I even asked my husband if we could do Valentine’s Day the next night so I could go to this event. He was not so keen on the idea.