Harboring hilarious dating stories?  Dying to dish some dirt or reveal your most embarrassing one-on-one moment? With Valentine’s Day quickly approaching, now’s your chance.

While I typically try to shed light on the way guys think by answering any and all relationship or guy-related questions, it’s only appropriate that I offer an extra installment dedicated to personal accounts of the biggest, boldest (and most horrible) dating moments.  Beginning today, through Friday, February 5th, Chicagoans are encouraged to submit their very best dating story for the chance to win Valentine’s Day dinner for two on February 14th at none other than HUB51.

Hit me with your best encounter at askjerrod@poorlittlerichgirls.com.  What’s there to lose?  You’ll finally get that horrible, hilarious and possibly humiliating story off your chest and perhaps even win a romantic dinner with your sweetheart (or non-sweetheart) on the house, plus a guaranteed reservation for V-Day weekend.  The winner will be announced and the very best stories will be featured online on Monday, February 8th.

(Jerrod Melman)




Jerrod Melman is one of PLRG’s resident contributors who offers his witty wisdom in his bi-weekly column, “Advice from a Jerrk.” If you have relationship or guy-related questions for Jerrod, just send an email to AskJerrod@PoorlittleRichGirls.com. When he’s not working on his advice column, Jerrod is a managing partner of Hub 51, River North’s hottest dining, nightlife and social establishment created by him and his brother, R.J.

Originally published on February 1, 2010.