Monday is the first day of the rest of our lives! Gossip Girl Season 5 returns on April 2, 2012, with Episode 18, “Con-Heir.” And, by all accounts, this is going to be a doozy of an episode — with multiple failed attempts by Dan (Penn Badgley) and Blair (Leighton Meester) to finally get it on, the triumphant return of Jack Bass, and a special cameo by Dan’s Cabbage Patch Doll. Yeah, you read that right. Here’s our roundup of what to expect from Monday’s major episode:

Serena’s Major Struggle
Will Serena (Blake Lively) a take the reigns as all-secret-knowing Gossip Girl? This dilemma is a major focal point the next episode, show exec Josh Safran says. “Monday’s episode is very much about that struggle for Serena. But it’s like the Ring and Frodo,” he adds, referring to The Lord of the Rings’ sweet Frodo Baggins, who is tasked with undertaking a perilous quest to destroy Sauron’s Ring in the fires of Mount Doom.

Lily and Ivy Battle It Out
Lily isn’t taking Ivy’s scheming lying down — she’s preparing for a full-fledged war on the conniving girl who kicked her out of her own house. But Ivy’s not bringing a knife to this gun fight; she’s packing major heat as she brokers a new allegiance with Lily’s ex (and Serena’s dad), William van der Woodsen.

Do Dan and Blair Finally Have Sex?
Dair’s first attempt at consummating their epic love story may not live up to Dan’s expectations, as we’ve seen from his lackluster “Wow” response in the promo. However, TVLine reports the two are “in a slight different state of mind the second time they do it." Drunk Dairing? Blame it on the a-a-a-a-alcohol.

Jack Bass Is Back, But He Might Have Some Secrets
Chuck is majorly excited to have Uncle Jack back in town, and is even dedicating a hospital wing in Jack’s name. But did Jack really save Chuck’s life? We have a hunch this storyline isn’t all ponies and unicorns like it appears.

Chuck Is Going to Do Some Soul-Searching
As Chuck delves deeper into his family lineage, “Doors are opened that Chuck was not expecting to be opened,” Josh told TV Fanatic of the developing storyline. “Things happen that change his perspective on who he is.”

Chuck Turns to The One Person Who’s Always Been There for Him: Blair
While “Con-Heir” might be all about Dan and Blair, our fair Queen B hasn’t forgotten about Mr. Bass in all of the Humphrey hubbub. Chuck will soon be asking Blair to help him investigate his past, and that storyline will kick into high gear in Episode 19: “It Girl, Interrupted,” according to the synopsis.