The meaning of “cheeky” can vary depending on context and the culture or region in which it is being used. Generally speaking, however, when a guy is described as being “cheeky,” it typically means that he is behaving in a playful, somewhat mischievous, or even slightly flirtatious manner.

A guy who is being cheeky might make jokes or playful comments that are intended to be lighthearted and humorous, but which may also be a little bit provocative or teasing in nature. For example, he might make a sly comment about a woman’s outfit or appearance, or he might make a sarcastic remark in response to something someone else has said.
In some cases, a guy might use his cheeky behavior as a way to flirt with someone he finds attractive. This could involve teasing or playfully teasing someone, or using humor and wit to engage them in conversation. Some guys might use cheekiness as a way to show that they are confident, funny, and not afraid to take risks or push boundaries.
However, it’s worth noting that the term “cheeky” can sometimes be used in a negative or derogatory way. For example, someone might describe a guy as being “too cheeky” if they feel that his behavior is disrespectful or inappropriate. Additionally, some people may view cheekiness as being immature or unprofessional, especially in a more formal or serious setting.
Ultimately, the meaning of “cheeky” can be highly subjective and dependent on the specific situation and context in which it is used. In some cases, it may be seen as a positive or attractive quality, while in others it may be viewed as a negative or undesirable trait. As with any behavior, it’s important to consider the feelings and reactions of those around you, and to use your best judgment when deciding how to act and interact with others.