Suggestion here. Don't look at your scrabble date as a do-or-die, make-or-break event, or else you'll probably both be so nervous the whole thing will just be an ordeal. Enjoy your game of Scrabble, enjoy each other's company, and if things carry through to the next stage that night, great, if not, well, you've had a pleasant evening, and give it another shot a few nights later ...