How do you define "playing the game"? Definitely be yourself but hold back a little and play the game a little. Otherwise, you might emotionally move to fast and scare a guy off. Something small might be a turn off in the beginning but not after dating a while. Give a few examples and I'll share one guy's opinion.

Ask An Activist: BOTH. "Place your BEST foot forward!" Have you heard that quote before? Do not be who you are NOT, instead, make certain that all of the wonderful qualities that make us your character shine though. "Accentuate the positive." I bet you've heard that quote? When you go to an interview for a job, do you tell them about all of the bad jobs you've had and how all of your managers used and abused you? Absolutely not. If asked, you briefly mention the challenges, and end on a positive, "lesson learned" note. Same in dating. You don't need to be so forthright about all of the past drama you've experienced. If asked, briefly mention a challenge or two, and end on a positive, "lesson learned" note. He'll appreciate your optimism.

If you want more information on how to date successfully, you should check out my book: Good Job, Great Guy! Finding & Attracting the Man of Your Dreams--the Boss's Way!

There's a favorite quote that I love to think back on: "This above all: to thine own self be true..." If you're not confident enough to be yourself then you resort to games. In my experience, those who can't accept you for who you are won't bother you and those who are cool with who you are will make the effort to get to know you.