Loose Lips Sink Relationships is the 5th episode of the fourth season and 76th overall.

Because of Karen's advise, Grace and Nathan worry that their relationship is in trouble. Jack sets Will up with her boss Dorleen.


We don't do enough Math

After being tested, Grace and Nathan share the number of their sexual partners and find out that although Grace has been with more men, Nathan has had sex much more times than Grace.

After separately consulting with Karen, Grace worries that she and Nathan are not having enough sex and Nathan worries that they need to share something deeper. As Grace chases Nathan around the apartment trying to have sex with him, Will tells them that they should not have taken advise from Karen and reassures them that their relationship is fine.

Think I might be purdy

Ep 04 05-0

I though we were being aggressive.

In order to take a night off from his new work at Barneys, Jack sets his boss Dorleen up with Will under false pretenses—she thinks Will is straight and is interested in her; Will thinks she is eyeing him to be a "real people" model for the store.

The plan backfires when believing he is there to audition, Will walks in on Dorleen in her bra, who in turn believes she is about to hook up with Will. As a result, Jack gets demoted to being the hand-cream guy, the "lowest form of life at Barneys".






  • Jack starts working for Barneys New York in this episode, after getting fired from Banana Republic. His boss Dorleen also appears for the first time.
  • Title is a play on the idiom "loose lips sink ships", a precaution on talking about confidential matters--in Grace and Nathan's case, the number of their sexual partners.
  • Karen and Nathan imply doing kegel exercise.

Cultural references

  • Will says they have been getting tested "since Frankie went to Hollywood", referencing the 80s band Frankie Goes to Hollywood whose vocalist Holly Johnson was diagnosed with HIV in 1991 shortly after the band broke up.


I don't know, Jack. Think I might be purdy. Will

Thrilled to be here. Love you. Love everything about you.
Thinking about being you for Halloween.
Jackto his boss Dorleen

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