If you needed any reminders that the characters on The Young and the Restless aren’t afraid to take big chances, here they come — in abundance! In Soaps.com’s latest spoilers for Monday, May 23, through Friday, May 27, Billy makes a bold move, Victor makes a decisive one, and Diane makes the kind that could get her killed all over again. Plus, as Jack and Phyllis ponder their future, Chance sees a troubling amount of Devon in his and Abby’s. Read on, and we’ll pour out the details on all of these teasers and more.

Young & Restless spoilers for Friday, May 20:

In Friday’s recap, Summer and Kyle bar Ashland from Harrison, Esther gets a hit on a dating app, and Ashley confronts Phyllis!

Here’s a pair that needs no reminding that two heads are better than one: Phyllis and Ashley discuss Diane’s latest move. The question is, will they be able to come up with a countermove to thwart the thorn in their sides?

Mother’s Day has come and gone, but Chloe may still have found the perfect present for Esther when she helps her mom start a new chapter. Maybe Katherine’s former maid is going to become an exec at Newman Enterprises or Chancellor-Winters! (Everybody else has!)

When Kyle faces a major decision, you can bet that it has to do with his back-from-the-dead mother. Or will it? Perhaps the Abbott heir will be facing a complex choice of a different nature.

We’ve all done it… and if you haven’t, well, you might want to try it… See Courtney Hope as you definitely never have before.

Young & Restless spoilers week of May 23:

Young & Restless spoilers for Monday, May 23:

In Monday’s recap, Diane meets Harrison, Lauren confronts Ashland, Victor finds Locke’s Achilles heel, and Esther goes on a date.

We wouldn’t want to be in Ashland’s shoes right about now. When Victor discovers his foe’s Achilles’ heel, you can bet that he will stop at nothing to exploit that weakness and banish Victoria’s latest spouse from their family — and Genoa City — for good.

When Summer and Chelsea talk shop, perhaps a new plan will be stitched together — one that will help ill-fated Rey’s unrequited crush put the spring back in her step. Maybe Kyle’s missus wants to recruit the designer for Marchetti?

Nikki had to see this one coming. So when her credibility is questioned, expect the  exotic dancer-turned-politician-turned-Newman Enterprises CEO to have no trouble defending herself. She can even refer to our photo gallery that tells her triumphant life story.

Young & Restless spoilers for Tuesday, May 24:

In Tuesday’s recap, Adam hatches a plan to distract Victor, Elena warns Nate about Imani, and Nick issues an invitation to Sharon.

Oh, Billy. Will he never learn? Rhetorical question. Of course he won’t. Today, he makes a bold move. But will it be a smart one? We’ve consulted our handy Magic 8-Ball on the matter and “Outlook not so good.” Shocking.

Speaking of grim prospects, Amanda learns disturbing news. Has Imani gone too far in her pursuit of Nate? Is a health crisis on the horizon for Devon’s lady love? Or is something altogether different about to go wrong?

Never content with the amount of power they wield, Adam and Sally size up the competition. They really do seem to think that they only way to get a leg up is by taking someone else down, don’t they?

Young & Restless moppet goes bad — real bad — as the ultimate terrible teen.

Young & Restless spoilers for Wednesday, May 25:

In Wednesday’s recap, Kyle needles Jack, Phyllis warns Summer, Ashland’s apology falls on deaf ears, and Victoria breaks up Diane and Nikki’s catfight!

This is going to require diagrams and flowcharts. Maybe an interpreter, too. When Jack and Phyllis dissect their relationship, will they finally come to the conclusion that we long ago did — that they are destined to see if they can not only get together again but stay together?

Bad move, Diane. She pushes Nikki too far, perhaps forgetting how easy it was for all of Genoa City to believe that Victor’s wife really had murdered her once upon a time.

Popcorn time! We’re already salivating at the prospect of watching Victor shut down Ashland’s apology tour. Some things, “sorry” just can’t fix!

First look! Chicago Fire’s ‘Stellaride’ wedding party… plus, trouble for Brett and Casey, and a Violet teaser for the season finale!

Sending love! Young & Restless alum Adrienne Frantz gave a troubling update on Baby Killian, who was hospitalized with high fevers.

His life in pictures: As the son of Jason Thompson turns 6, look back as he grows from a precious baby to a ‘fun, little human’.

Young & Restless spoilers for Thursday, May 26:

In Thursday’s recap, Phyllis freaks out after Kyle asks Diane to stay, Lily questions Billy, Nate bonds with Imani, and Jack refuses Ashland’s request.

Apparently, Victor is on a real tear this week! Only a day after he tells Ashland where he can shove his mea culpas, he gives Diane a warning.

Hmm. If Chance struggles with Devon and Abby’s bond — and he does — is the stage being set for the blonde’s husband to possibly turn to a certain someone else? One of Soaps’ editors is already shipping the potential couple, even if she also feels hella guilty about it! Find out why here.

No doubt stemming from his “bold move,” Billy lands in hot water with Lily. Did the avid podcaster go out on a rickety limb and start naming names?

Get your first look as Hunter King takes her new character on a romantic Hallmark adventure!

Young & Restless spoilers for Friday, May 27:

Given that Summer doesn’t trust Diane as far as she could throw the luggage she struggled to get over the Abbott threshold, it should be easy for Phyllis to recruit her daughter to help take her on. Certainly, Kyle’s wife holds more sway with him than does his conniving mother. Um… right?

Given that Chelsea suffers a setback, we’re going to assume that her shop talk with Summer doesn’t leave her seeing the world sunny side up.

As he always has, Jack protects Kyle’s best interests. Our immediate thought: What has Diane done — or what is she trying to do — now?

At a time when we all might need something to lift our spirits, Melissa Ordway lets us listen in on a daddy/daughters sing-along that’ll warm your heart: “These moments mean everything to me.”

Join us as we say goodbye to another beloved soap vet, who will be remembered from her time on Guiding Light.

Ready for a heated debate? We’ve ranked Young & Restless‘ 25 all-time best couples. See if you agree with who landed where! 

— Candace Young/Charlie Mason