I was scanning radio stations on a stormy morning commute when I stopped on Q105. They were hosting a contest. A “Meet Harry Connick Jr. and have lunch with him” contest! OH MA GAWD!! This was MY chance. The catch: I had to sing “It Had to Be You” on the air, live. And then it was completely up to the listening public to call in and vote on their favorite rendition. Hmmm, my incomplete vocal lessons might get in the way between me and my favorite Southern crooner. So I began to practice. I sang and sang and sang some more until I felt I hit every note just so. I was beyond Girl Scout prepared for my chance to call in and give it my best shot the next morning. 4 a.m. and I’m woken up with panic riddled thoughts, “You can’t just sing the song! You have to make it different. But how? The challenge is to sing “It Had to Be You”. How can I stray from that? Humor. Inject it with humor. Yes, that’s it. Make people laugh and you’ve broken through to the next level.” And so I morphed my perfectly crafted classic into a cheesy ballad, highlighting the radio station sponsoring the contest (flattery gets you everywhere!) and crossed my fingers that the city of Portland would validate my inner comedian, especially since I wasn’t so sure my inner singer would take me very far. Well, it worked. 68 early morning callers made the effort to call in and vote for ME! What did this mean? Besides changing everything and confirming that anything is possible? It meant that Halloween of 1991 was the best day EVER. It meant that I got to break bread with Harry (cue window opening for an opportunity of “sweeping him off his feet”). It meant that my seats were upgraded to front and center. It meant that dreams really do come true. Lunch was at the Heathman Pub in Downtown Portland. My nerves were out of control as the minutes between meeting the man of my dreams were diminishing. Big hair? Check. Shoulder pads? Check. (It WAS 1991 folks. Those things really were the style back then.) I walked into the room where Harry & I were to enjoy one another’s company for an hour only to discover that his 16 piece band had tagged along, along with about what seemed to be 30 people from the radio station, and another set of radio winners (Hi Laura! Hi Lorna!). Oh yah, and Harry’s girlfriend, Jill. The drop-dead gorgeous Victoria Secret supermodel, Jill Goodacre? Yah, that Jill. Well hell. Master Plan “Swoop”, scratched. I had to quickly gain my composure and go to Plan B; get over myself and enjoy this surreal moment immensely.
About this time, Harry comes back to the table to check in on his lady to see if she needs anything, “Daarlin’, can I get you sum caawfee?” Jill butts right in and exclaims, “Harry, this girl sang to get here!” Harry looks at me and says, “Well I ain’t leaving this room til y’all sang!”