Please provide a sentence where the phrase appears and/or any additional information that may be relevant in shedding some light on what you're asking about. Without this, it is impossible to give a good answer to your question.
If the sentence came from a book I would provide a better context. The way it is now it doesn't make sense, unless it's an expression used outside the U.S. I can only think of one expression that even comes close to what you wrote but it is not a good thing. We say "X has his/her head in the clouds". This means the person is not in touch with the reality of a certain situation. As you can tell, this wouldn't be the type of person a woman would want to date.
Maybe the author is trying to say a man that is usually in good/happy mood.