Gary's Wrapkin business is doing well, but to really take it to the next level, he's going to have to get it carried in a big box store. The problem is, as long as Yoda and Clark are his assistants, the Wrapkin's going nowhere. When Marny's sister Bridget comes to visit, Marny takes initiative and offers her sister as an assistant to Gary. Gary is not enthused, since Bridget hasn't worked a day in her life. Regardless, Bridget accepts the job. Her first accomplishment? Taking a personal day.
Elsewhere, Sheila and Chris are moving ahead with their artificial insemination plan. Sheila has one vital request for Chris - he must promise not to tell Nick. But when Chris tries to keep things under wraps at Nick's house later, Sheila gleefully reveals their plans. She just wanted to see the look of devastation on Nick's face. Sensing that Sheila's up to something even more sinister - like reconciliation - Nick sets out to save Chris before it's too late.
It's 10:30 a.m. on Bridget's first full day on the job, and she's already fed up with the corporate grind. Marny's had enough with her sister's lazy attitude towards life. She encourages Bridget to step up and get creative with her work. Soon, Bridget has created a new, more feminine and stylish design. Gary hates it. He asked her to be his assistant, not redesign the product! Amid the fight, Bridget quits.
Chris comes around to the artificial insemination idea after taking a tour of the facilities, but Sheila's beginning to get cold feet - after all, the doctor drives a Saturn - can you trust that? She suggests they forgo their plans and have the baby the old fashioned way. Chris quickly agrees, even though Sheila assures him it will be clinical, efficient and zero fun.
Nick devises a plan to convince Chris to steer clear of Sheila. He hosts a "Never Should Have Married Sheila" party at Cagney's complete with life-sized posters of low-points in Chris' awful relationship. Ever wary of Sheila, Nick's going to encourage Chris to instead reconcile with his old girlfriend, Sage. Chris is still unconvinced.
The manager of Forever Babies, a big box store, calls Gary in for a meeting and raves about his Wrapkins. A sale in hand, Gary congratulates himself on his salesmanship, thinking he didn't need Bridget after all. But when the manager informs Gary that the new designs are what convinced him to buy, Gary realizes that Bridget dropped off her prototypes to Forever Babies and ultimately closed their first big deal.
Back at the party, Gary apologizes to Marny and Bridget for doubting Bridget, singing Kelly Clarkson's "My Life Would Suck Without You." Meanwhile, Chris is tired of Nick's ridiculous tactics. He sets off to go make a baby with Sheila, but bumps into his ex, Sage, at the door. It's a set-up!
As the party begins to wane, Chris seems to really be hitting it off with Sage; maybe Nick is right that they're made for each other. Suddenly, Sheila shows up at the party unnoticed and asks Chris where he's been. They had an "appointment" that he missed. But when Sheila sees Sage, she leaves, extremely embarrassed. Faced with the prospect of dating Sage or reconciling with the mother of his baby, Chris just doesn't know what to do. It's an existential crisis.