I don’t know the name of the movie or any of the actors. It’s based in Washington DC in the 2000’s.
It involves a recent male graduate from George Town or George Washington, cum laude. He has a female roommate. They’re having trouble paying rent.
He sleeps with older women. In one scene with an older female, her wig falls off.
His female roommate is a hacker who has incriminating videos of politicians/judges. She stores them on USBs in a box. One of her victims is an anti-gay judge caught in having gay sex.