Today is Sweetest Day, that odd Hallmark Holiday that remains the awkward teen stepsister to the slightly more tolerable and decidedly more popular Valentine’s Day. I first heard of Sweetest Day years ago when I was a floral designer in Chicago and some poor guy came into to the shop on his lunch break throwing around twenties and begging me to create the most gorgeous Sweetest Day bouquet money could buy. “I need to convince my girlfriend not to dump my ass,” he whined. “Well, why would she dump you? What did you do?” I asked. “I cheated on her,” he replied. And that’s when Sweetest Day was forever branded in my mind as the occasion to atone your relationship sins…or at least spend a bundle on flowers trying. That impression was further molded a couple years later when I was on a first date with a guy who, while flipping through his planner before the movie started, said, “Oh, crap! Sweetest Day is this weekend. I gotta get something for my girlfriend.” “Your girlfriend?!” I asked in disdain. “Yeah, she’s great.” He answered. I opted to skip drinks with him after the movie ended.
So, here’s to Sweetest Day…and hoping none of you get surprised with a gift from your sweetie this year.