When should I ask my girlfriend to be my Valentine? Is there a particular moment that would render the proposal more romantic or enchanting? Could it be before a significant date, perhaps during a leisurely evening stroll under a starry sky, where the ambiance is simply perfect? Or might it be wiser to choose a more casual setting, such as among friends, where the playful banter sets a light-hearted tone for the inquiry? What about considering her personality – does she thrive on spontaneity, or does she prefer a more thought-out approach? Would her enjoyment of surprises suggest that an unexpected declaration could leave a lasting impression? Moreover, how can one gauge the ideal time without overthinking and risking it all? Should I take her mood, the current stage of our relationship, and even the time of year into account? Ultimately, what factors should decisively influence this momentous decision?