This eclectic, star-studded anthology follows diverse Chicagoans fumbling through the modern maze of love, sex, technology and culture. First dates, friends with benefits, couples with kids. Whatever your relationship status is, it's always complicated.

A gambling addict faces a conflict when entrusted with keeping a bunch of money that isn't his.

When Jeff discovers that the bowling alley he manages is being sold, he must do everything he can to save the place he's come to call home.