Based on the CBS episode of Thursday, October 15, 2026, and the published Billy Abbott history at Soaps.com.
At Thursday’s rehearsal dinner, the first question Sally’s family sent Billy on video was blunt. Coco read it out from Grams: “Billy, this isn’t your first rodeo. Convince us you won’t tank this relationship, too.” Billy winced — “Jeez. Damn Grams” — and then answered: “Historically, you could say that I am a screw-up. And by you, I mean my siblings here, because they’ve told me so many times over… The truth is, I have been the author of my own misery. No one to blame but myself. But I promise you that I will never willingly hurt somebody. She has a heart of gold.”
Later, after the toasts, Ashley told Jack what she really thinks: “It’s no secret that Billy’s had a very difficult time dealing with failure in his life. I can’t help it. I’m worried about this marriage. Can Billy handle another loss?” Jack, for his part, had just said: “Am I crazy or is this a love that could last?”
So what exactly is “another loss”? Here is Billy’s record at the altar — three brides before Sally — and how each marriage ended.
1. Mackenzie Browning — 2003
Billy’s teenage love. Per Soaps.com’s character timeline, Billy and Mac married in 2003, then learned they were first cousins; the marriage was annulled and both left Genoa City. Years later the cousin story fell apart — Jill turned out not to be Katherine’s daughter — and the two tried again in 2009, but it did not last.
2. Chloe Mitchell — 2009
When Billy was revealed as the father of Chloe’s baby Delia, he married Chloe. Soaps.com’s timeline records that he slept with Sharon the day before the wedding and later reunited with Mac; the marriage ended in divorce. Delia, Billy’s daughter with Chloe, died in 2013 after a hit-and-run — the loss that defined the next chapter of his life.
3. Victoria Newman — 2010, and again
Billy and Victoria got drunk and married in Jamaica in 2010. The marriage collapsed in 2011 after Billy bought a baby, Lucy, in the wake of Victoria’s miscarriage; Phyllis won custody of Lucy and Billy spiralled, ending up in a Myanmar jail from which Victor bailed him out on condition he stay away from Victoria. He didn’t. Billy and Victoria remarried over the 2011–12 holidays and raised Johnny (Chelsea’s son, whom they adopted) and later Katie. After Delia’s death, Billy’s affair with Kelly Andrews came out, Victoria filed for separation, and the second marriage ended in 2014. Soaps.com sums up the years that followed in one caption: “If at first (or second or third) you don’t succeed…”
The near-misses that never reached the altar
Three more relationships ended without a wedding. Chelsea Lawson, 2015: they planned to marry; it ended when she cheated with Adam. Phyllis Summers, 2017–18: ended when Billy slept with Summer after Phyllis cheated with Nick. Lily Winters, 2020–24: ended when Billy left to support Chelsea — who then slept with Adam again. Billy and Sally became a couple in late 2024.
Why the question lands this week
Victoria, the bride of marriages three and four, spent Thursday’s episode with Kyle while the Abbotts toasted Sally — and told Victor, “I’m at a friend’s place.” Johnny and Katie return for the wedding on Friday and Monday, per Soap Opera Digest. Ashley’s question is not about Sally’s past; it is about whether Billy survives it if this one fails too.
What’s next
Soaps.com’s Friday spoiler: “Sally and Billy’s family and friends gather for the epic wedding,” with “the arrival of a surprise guest.” TVLine says the ceremony concludes Monday, October 19 with a “shocking” finale.
Your call: Three marriages, three endings. Is Ashley being unfair to Billy — or is she the only Abbott saying it out loud?
Sources: CBS episode of Thursday, October 15, 2026 · Soaps.com — Thursday recap: Ashley Predicts Doom for Sally and Billy · Soap Central — Y&R Recap October 15 · Soaps.com — Billy Abbott timeline gallery · Soaps.com — Billy Abbott character profile · Soap Opera Digest — Johnny and Katie return (Oct. 14, 2026) · Soaps.com — Spoilers October 12–16 · TVLine — Sally and Billy’s Wedding Begins.