Diana's relationship is going well except for one, teeny-tiny obstacle -- his overbearing Italian mother that thinks she knows what's best for her "baby boy."
Pulling the typical "college girl sneaking out in the morning," Diana runs into mama who invites her over for a family dinner so everyone can meet the woman that stole Enzo's heart.
She orders her to bring a dish but being unable to cook, Diana opts to order from her favorite restaurant.
Liza suggests Maggie make her incredible lasagna and upon hearing that it's so good, it makes folks cry, Diana agrees.
Mama puts Diana on kitchen duty and very quickly realizes that she's faking it and isn't the chef behind the lasagna.
When she calls her out at the dinner table, Diana reaches her breaking point and throws in the towel.
"I'm too old for this," she exclaims which mama agrees with.
However, Enzo doesn't seem to agree with his mother and he finds Diana on the ferry into New York.
He assures her that mama won't be controlling his life anymore because he's getting an apartment in the city so they can continue their relationship.
Josh is gearing up for the re-opening of Inkburg. He signed a 10-year lease and remodeled the insides which Kelsey says is still an attempt to impress Liza.
Liza is impressed with what Josh has done with the place and during his speech, he thanks Liza for continuously inspiring him and encouraging him not to give up.
Liza is shocked to see her daughter, Caitlin, at the opening but apparently, she and Josh are Instagram friends now.
She's also in town for a wedding with her much older boyfriend which Liza finds appalling.
Caitlin points out the oddity -- her mom is dating a much younger man, she's going older -- and Liza agrees to a bonding brunch.
The next day, the four of them go out for the world's most awkward brunch.
Greg admits to once being Caitlin's English professor and assures Liza they "severed their academic relationship when things got personal."
None of that eases Liza's concerns.
Greg also admits that they are keeping the relationship a secret until he makes tenure which Liza can relate to all too well because of her current situation with Charles.
After brunch, Josh encourages Liza to force Caitlin to "end it," however, she knows that would make her a hypocrite.
She comes clean about her relationship with Charles to Josh and at that moment, he realizes he's been foolish to think that he could ever have another chance with Liza.
He admits that he's only ever been serious about her and never once wanted to keep her a secret like Charles has.
Then, he makes the decision to permanently erase the tattoo he got for her.
Hearing that makes Liza feel less than and when she sees photos of Charles on his work trip with Quinn, their new author, she gets jealous.
Even Maggie seems to think Liza is just a "side piece" to the boss.
When Caitlin comes to her house crying that the wedding was a disaster and Greg made her leave because someone else from the faculty was there and would have figured it out, Liza decides to tell her the truth.
Caitlin is shocked that her mother has been able to pass as a 27-year-old this whole time.
"Have they seen you in daylight," she asks baffled.
Liza drives home her point -- you should never allow yourself to be a man's secret.
When she sees Charles later on, she makes him aware that she's not comfortable with their workplace affair.
"Now's just not the right time," Charles tells her seemingly confused because they'd already discussed keeping things on the down-low.
"Call me when it is," Liza says as she walks away leaving Charles stunned.