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When we say ברכת החודש on the שבת before חודש אב, we ask ה׳ to give us a month full of ששון and שמחה. However, the משנה in תענית פרק ד משנה ה, the רמב׳׳ם in הלכות תעניות פרק ה הלכה ו, and the שולחן ערוך in אורח חיים סימן תקנא סעיף א all say that when the month of אב comes, we're supposed to lessen our שמחה.
How can we pray that the month of אב be a month full of שמחה when the הלכה clearly says that we lessen our שמחה in חודש אב?
Technically, we ask for "a life of happiness", and that this month be one renewed for happiness. No one said the month was full of happiness, per se.
On one level, we pray that it be converted to a month that's fully glad, when we're no longer mourning the destruction of the Temple.
More simply, I recall a talk from Rabbi Pesach Krohn (don't recall who he quoted) that there may be less joy this month, but that statement takes for granted that there must always be joy.
