Well, it depends on what the guys personality is like. If you think the guys likea hare to get then just play around. You may not want to go too far though or else they may give up on you. Give little hints now and then that your still into him though.
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Some guys may enjoy a challenge because it adds excitement and keeps things interesting. However, every individual is different, and some may prefer a more straightforward approach. Communication is key to understand what someone enjoys in a relationship.