Why Dating a Friend’s Ex, Simon Cowell Style, Can Work

Simon Cowell and Lauren Silverman.
Simon Cowell and Lauren Silverman. Photo: Getty Images

The world found out this week that X-Factor judge Simon Cowell knocked up his friend’s soon-to-be-ex-wife, Lauren Silverman. (She and her husband, real-estate mogul Andrew Silverman, are in the process of divorcing.) This is bad form on both Cowell and Silverman’s part, but it’s probably a much more complicated situation than we’ll ever understand, even though we’ll certainly hear more than we ever wanted to from the tabloids. Perhaps by coincidence, today’s Times included a story about couples who try to save troubled relationships by going on vacation together, with mixed results. For one couple, the trip ended with a spouse swap, not terribly unlike Cowell’s situation.

Jessica Chafetz, 36, a dietitian from Bellmore, N.Y, is still aghast about a last-resort cruise to the Caribbean she took in 2008 with her husband of seven years.

The cruise was booked a year in advance, but she and her husband decided to forge ahead anyway, in part because their best friends — a couple who was also having troubles — were coming.

Big mistake. “My husband and my best friend kept disappearing together,” Ms. Chafetz said. She recalls one particularly excruciating evening when the two couples dropped into the ship’s nightclub as the steamy song “Low” by Flo Rida came on. Ms. Chafetz watched in horror as her best friend “got all on top of my husband” on the dance floor.

On the last day at sea, her best friend announced that was she quitting marriage counseling. Two days later, Ms. Chafetz’s husband said he wanted a divorce. Before long, the two were openly dating.

But all was not lost. As both divorces were finalized, Ms. Chafetz and the other husband turned to each other for solace. And eventually romance. Two years later in a dramatic swap, the former best friends married each other’s spouses. (No, they did not attend each other’s weddings.)

See, sometimes what begins as the ultimate betrayal turns out for the best! It’s not an ideal situation, and we certainly wouldn’t condone infidelity, but it’s not outside the realm of possibility that your best friend’s lover could love you, too — or instead. Hearts may get broken along the way, but sometimes these scandalous, borderline incestuous couplings result in very happy relationships. We’ve rounded up a few (anonymous) anecdotes from around the office; feel free to add your own in the comments.

The Girl Who Wound Up With Her Jail-Visit Buddy
“Back in college, I knew a group of guys who were on their way to a Phish concert when the driver lost control of the car. They went over the median and killed someone who was coming from the opposite direction. None of the other guys in the car were hurt, but the driver, Tom,* wound up doing prison time, about a year. He had a serious girlfriend at the time, Annie, and she would go visit him in jail, often with his best friend, Alex. Annie and Alex started bonding and leaning on each other over the course of the prison sentence, and eventually she broke it off with Tom. Now she’s married to Alex, and they have kids and law degrees. Tom doesn’t talk to either of them. I believe he’s still single.”

The Middle-Aged Divorcés Who Wound Up With Each Other
“My parents had a group of friends in the neighborhood, all couples, who would get together for dinners regularly. When I was in my teens, two of the couples — who were particularly good friends with each other — got divorced around the same time. A few months later, the wife from one of the former couples, Judy, got together with the husband from the other, Terry. They’ve since gotten married, and seem extremely happy. My parents insist that Judy and Terry never “got together” before they were officially divorced, but that they were just ‘really close.’ Their relationship has complicated the group dinners, though; to avoid awkwardness, the remaining ex-spouses no longer get invited, which seems sad.”

The College Friend Who Wasn’t Over Her Ex After All
“I went to a small college, and one of my close friends, Cara, dated this guy Dave. They were together for only a few months, I think sophomore year, and then she dated someone else for the rest of college. So when Dave and I started hanging out at the end of senior year, I mentioned to her that I was interested in him. She was like, ‘Go for it! You have my blessing! He’s great!’ He and I finally got together, and when I told her, she freaked out. I thought she’d get over it, but she and another girl sent me a bunch of weird text messages. Dave and I wound up dating for a few months; it never got terribly serious. But it definitely ruined my friendship with Cara, who in retrospect wasn’t a great person anyway. Even though things didn’t work out with Dave, it taught me: a) it’s probably not good to date a friend’s ex, but b) if you do, sometimes it’s worth it to lose that friend.”

* All of these names have been changed, for obvious reasons.

Why Dating a Friend’s Ex, Cowell Style, Can Work