Ruby continues to flirt with Bryant, who insists he's committed to Jennifer. Ruby doesn't want a relationship; she just wants to have fun. Bryant is tempted by Ruby's offer: a secret no-strings attached affair while he dates Jen. Jennifer confesses to Barbara her fear that she'll lose Bryant to Ruby. Barbara encourages her to stick to her guns and follow her heart. Bryant comes over to see Jen and tries to convince her - and himself - that he's not interested in Ruby. Meanwhile, Barbara contemplates what do about her marriage. Chris and Emily have another roll in the hay. Chris tells Emily he has discovered a gap in Henry's resume, which could indicate he was involved in something scandalous in Chicago.