A personal audio device including a flexible headband is disclosed. The flexible headband includes a left and right headband portion. The headband has a longitudinal centerline which occupies a substantially single plane. The personal audio device also includes a left earphone, which is secured to a first end of the left headband portion, and a right earphone, which is secured to a first end of the right headband portion. A connector portion connects a second end of the left headband portion with a second end of the right headband portion. The connector portion is linearly adjustable, which enables a distance between the left headband portion and right headband portion to be variable. A change in the distance causes an inversely proportional change in bent compression force applied by a left earphone and applied by the right earphone.