Described herein are various embodiments of flexible catheters comprising one or more flexibility regions. In one embodiment, a catheter comprises an elongate body having a proximal segment and a distal segment; a first lumen defined by the elongate body and configured for drainage of a liquid from a bodily region; and a plurality of flexibility regions on or in the distal segment of the elongate body. The plurality of flexibility regions, collectively, is configured to passively bend anteriorly. Further, at least one of the plurality of flexibility regions has a defined percent volume of material removed and a defined cut depth percentage. The features and arrangement of the flexibility regions described herein result in the catheter requiring reduced force during insertion into a bodily lumen.