A Look at Larry King's Ups and Downs Over His 8 Past Marriages — A Complete Relationship Timeline

For the eighth time in his life — ninth if you count his previous annulment — Larry King is headed towards divorce.

On Tuesday, a lawyer for the television personality, 85, confirmed to PEOPLE that he was filing for divorce from his current wife, Shawn Southwick King, after nearly 22 years of marriage.

The couple had weathered allegations of infidelity, and Larry originally filed for divorce in 2010 before retracting the paperwork.

The CNN host is no stranger to marital strife — Shawn, 59, is Larry’s seventh wife, though he has been married eight times total. (He remarried his ex-wife Alene Akins in 1968, five years after they divorced.)

Here’s a look at Larry’s ups and downs over his past eight marriages.

FREDA MILLER: 1952-53

Larry married his high-school sweetheart at age 18. The next year, the marriage was allegedly annulled by their parents, who didn’t approve.

ANNETTE KAYE: 1961

For less than one year, Larry was married to Annette, who gave birth to his first son, Larry Jr., in 1961.

ALENE AKINS: 1961-63

Larry was married to Alene, a former Playboy bunny, twice and adopted her son Andy during their first marriage.

RELATED VIDEO: Larry and Shawn King Break Their Silence (and Hop into Bed Together!) Amid Cheating Rumors

MICKEY SUTPHIN: 1964-67

Mickey, the mother of Larry’s daughter Kelly, divorced him two years after they were married.

ALENE AKINS (AGAIN): 1968-71

During their second marriage, Alene gave birth to their daughter, Chaia.

SHARON LEPORE: 1976-83

After he split with Alene, Larry met Sharon a production assistant and former math teacher.

RELATED: Larry King and Seventh Wife Shawn Divorcing After Nearly 22 Years of Marriage

JULIE ALEXANDER: 1989-92

Julie, a businesswoman, met Larry in 1989. She would become his sixth wife later that year when the two married in Washington. They separated in 1990, two years before they officially divorced.

SHAWN SOUTHWICK: 1997-2019

Larry and Shawn, 59, wed on Sept. 5, 1997. They share two sons: Chance, 20, and Cannon, 19.

On Tuesday, August 20, however, Larry filed for divorce in Los Angeles Superior Court. He cited irreconcilable differences, and the date of separation is listed as June 6, 2019.

The Kings’ marriage was a rocky one: In 2010, Larry filed for divorce after the National Enquirer reported that Shawn had an affair with one of their sons’ baseball coaches, Hector Penate. Penate later admitted to the affair, but the couple decided to stay together.

Six years later, sources confirmed to PEOPLE in 2016 that the broadcast icon was distraught about another alleged yearlong affair his wife had been having.

“It’s true, and Larry is completely embarrassed and anguished by all of this,” one source close to the situation told PEOPLE of the alleged infidelity. “He doesn’t know what to do.”

Another insider claimed to PEOPLE that Shawn, a former singer and TV host, told her alleged lover that her marriage to Larry was over.

Despite those reports, Larry and Shawn denied any reports of cheating in an interview with Home & Family in August 2016.

“You said an interesting word, ‘rumor.’ I’ve been in the business — next May, it’ll be 60 years — and I’ve dealt with rumors a long time,” he said. “Interviewed people involved with rumors. Rumors are what they are — they’re rumors. And I tell you the truth, I don’t pay any attention to them.”

Added Shawn: “Last week, there was a rumor going around about Larry and a speech he made in Kiev. This week, I’m the latest pinup girl. You just have to develop a shell around yourself and not get hard on the inside, and stick together.”

The couple appeared to have moved forward until Larry filed for divorce for the second time on Tuesday.