Jack Flirts With Ryan Phillippe On The Latest ‘Will & Grace’

Credit: NBC

The episode begins with Grace getting excited over seeing her niece Fiona (played by Billie Lourd, who happens to be Debbie Reynolds granddaughter. Debbie played Grace’s mom on W&G prior to her passing) before gushing to Will about them eventually being the coolest parents.

Jack and Karen then enter the apartment where he says that Estefan is flying him first class to Miami for their “One Queer Manniversary.” Karen decides to fly “commercial” much to the shock of Will as she’s scouting a third baseman from Cuba for her baseball team.
Karen then has a meltdown on the plane when she thinks her seats are all the way in the 3rd row of first class or as she says, “Where Melania puts Tiffany?”

Things only get worse when her assistant Amy says they are actually in coach. Karen is once again confused. “With the paychecks to paychecks?” Things become more hilarious with them later on in the episode when she’s served a tiny bottle of vodka from the stewardess. “THEY SHRUNK THE VODKA!”, she yells.

Meanwhile Jack is seated next to Ryan Philippe, who happens to be his biggest celebrity crush. Estefan gives him permission to hook up with Ryan which becomes confusing for Jack because he wasn’t happy with the idea of them having an open relationship this quickly into their marriage. Things eventually work themselves out in the bathroom where Jack and Estefan discuss their marital differences with Ryan watching from behind (who appears clueless the entire time that Jack really wanted to hookup with him).

Back to the other storyline. We meet Fiona who warmly embraces W&G before introducing them to her boyfriend Trevor. He enters in a highly dramatic setting and announces that all the seats for The Devil Wears Prada musical in NYC & Chicago are sold out. Neither W&G believes he is her boyfriend as they are under the assumption that he’s the Will to her Grace, in other words… gay.

W&G then look totally confused when she finally reveals that they are a couple and that Trevor is actually bisexual. Will then has a heart to heart with Trevor where he tries to convince him that he’s actually gay, much to his own shock and confusion.

Grace has a similar convo with Fiona, relating to her past with Will when they were in college after they were at item and before he came out, but all she does is say how great Trevor is in bed (using cookie as a reference for her private parts and saying he can’t get enough of it).

W&G are hellbent on thinking that Trevor is gay and the four of them have it out about it before the episode ends. Trevor & Fiona make them realize that their mindset of bisexuality being a sleigh ride into homosexuality is archaic, or “so 90’s,” which makes W&G both understand and cringe at the same time.