In a last-ditch effort to keep Millennial afloat, Kelsey and Charles travel to Chicago to meet with a group investors.
Charles leads much of the presentation with Kelsey stepping in as the younger voice that will lead the company into the future.
The room of male investors is impressed and they agree to fund Millennial.
Celebrations are aplenty with Kelsey's get a little out of control when she accidentally posts a celebration sext meant for Zane's eyes only to her public Instagram account. Oops.
The next day, not only is Kelsey a meme but she's also out of a job.
The investors threaten to pull their funding unless Charles Brooks resumes the duties of a publisher.
Despite his protests, Kelsey steps down from the position to save the company prompting her to throw herself a pity party telling Liza that "last night she had it all."
Meanwhile, Liza is shocked to see a 20-foot photo of her and Josh getting a little too flirty staring back at her smack dab in the middle of New York City.
Since the Infinitely 21 campaign is regional, she's not too worried about Charles seeing it while he's in Chicago.
But when Lauren informs her that the success of the campaign convinced the company to take the ad nationally, she books the next flight out to Chicago to make amends.
Charles is taken aback by the ad, but he understands that she has a past.
He's more concerned about why Liza felt it was necessary to fly out to Chicago to warn him about it.
Liza promises to leave her past in the past, which means not seeing Josh anymore.
Josh is equally as thrown off by the giant ad, but it's the least of his problems.
Claire informs him that she got a job offer with Google and wants to take it to ensure a good life for Gemma.
The only problem is that the job is in Los Angeles.
Josh doesn't feel comfortable with Claire moving so far away with his daughter.
When Maggie's suggestion of getting a lawyer and seeking custody falls flat, she tells him to take advantage of his newfound press.
Josh pays Infinitely 21 a visit a proposes a partnership that would feature exclusive Inkburg tattoos in their stores.
Shelly thinks it's a fabulous idea mostly because she's smitten with Josh, and a new gig is born.
The Diva goes wedding dress shopping with Lauren and realizes that finding the right man calls for an extravagant dress that only Diana can pull off.