Dress for the occasion. You don't have to run out and buy a fancy tennis skirt with pockets to hold the balls, but athletic clothes that allow you to move freely are necessary. Be sure to put on a pair of comfortable tennis shoes and don't forget an extra layer of deodorant.
Bring a water bottle to satisfy your thirst during the match. Include an extra one for your date if you think he may forget and you don't want to share your bottle with him. Throw in a couple of hand towels to in case you work up a sweat.
Decide upon the method of play. You can play a full match; best 2 out of 3 sets or you can just rally and take it easy on the court. At any rate, start by rallying to determine the playing level of your date. If you're a lot better than he is, you will have to tone down your game to keep from running him.
Compliment every good shot your date makes. If he's not very good, compliment him if he just makes contact with the ball. This rule holds true even if he's a lot better than you are. By complimenting him, you'll appear gracious and sportsmanlike.
Keep your cool. Perhaps you're a competitive soul and your date is beating the socks off you. Smile, be complimentary and hit the ball right down the line to keep him from returning it. You don't have to play poorly on purpose to satisfy his ego. If he wants a real match, give it to him, but don't lose your cool.
Make the date fun. Keep up the small talk and spend a little extra time when changing sides to comment on a good shot or a long rally.
- If competition brings out the worst in you or your date, end the match early and suggest going for ice cream. Alternately, if you have a great time, drop a hint during the match about how much fun it is and that you would love to do it again.