The Real Reason Tom D'Agostino And Luann De Lesseps Divorced

To even the most casual fan of The Real Housewives of New York, the news that Tom D'Agostino and Luann de Lesseps' marriage didn't work out shouldn't come as a big shock. The past two seasons of Bravo's reality series tracking the cat-fighting dramatics of a bunch of Manhattan socialites has almost entirely hinged on Luann's' perplexing decision to marry a guy who the rest of the cast couldn't stop calling a creep. And this time, they weren't just being melodramatic — by most accounts, Tom is the kind of guy from whom women shouldn't accept a free drink, much less a marriage proposal. Anyway, let's get down in the dirt on why this star-crossed union hit the skids.

It wasn't until Tom and Luann's relationship took a serious turn in season 8 that the rest of the ladies started raising their perfectly-plucked eyebrows. And though the drama spilled into season 9, with Bethenny even tearfully telling Luann she was making a huge mistake two weeks before her wedding, Ramona and Sonja, in particular, had some very specific issues from the get-go.

According to Us Weekly, Luann announced her romance with Tom to the cast after they'd been together for only six weeks. And despite the fact that that's shorter than most high school relationships, she couldn't stop gushing about being "soulmates." Immediately skeptical, Ramona informed Luann that Tom "calls his ex every day and tells her he loves her, and he gave her a gold bracelet for Christmas!" After Tom and Luann got engaged, both Sonja and Ramona threw shade at her ring. Sonja said it was "murky," while Ramona politely informed the press that she felt Luann should have it appraised because "we really don't know what's in there." So why did these two sharpen their knives for Tom so quickly?

If there's such a thing as a Real Housewives groupie, Tom D'Agostino is it. Though his relationship with Luann went the distance, albeit briefly, he's been creeping on the RHONY ladies for years.

Somehow, Tom dated both Ramona and Sonja without each other knowing it before moving on to Luann. At least, that's according to Ramona, who told The Daily Mail, "I had no clue, no clue at all, that he'd gone out with Sonja. Otherwise I never would have dated him," adding that she felt Luann's initial advances towards Tom were aimed at making her jealous. Naturally.

Sonja revealed her past relationship with Tom by elegantly stating on the show, "My head is going to blow up. He may be her soulmate, but I've been doing him forever," according to Us Weekly. She later admitted to Vulture (via The Daily Mail) that what really upset her was the fact that she and Tom had a "friends with benefits" relationship that he refused to acknowledge to Luann for a long time. "The man has to make a woman feel special. He should have said, 'We were really good friends and we had something special, but then I fell for Lu.' That would have made us both feel special," Sonja said. 

So, how did Tom respond to Sonja's "friends with benefits" claim? "The funny part is, although I've known her for years, we got together once, but she's on this kick that it was more than that," he told People. 

At the end of season 8, the cheating accusations and past relationship drama came to a head when Bethenny dropped bombshell photographic evidence of Tom allegedly cheating. In true melodramatic fashion — and in front of Bravo's cameras, of course — Bethenny tearfully tells Luann, "I promise that there's nothing about this that I want to be doing right now," before she attempts to show Luann photos that a friend sent her of Tom allegedly making out with a woman at a hotel just days after his and Luann's engagement party.

This did not go over well with Luann, and when she confronted Tom over the phone, his big excuse was that he had "no recollection" of the incident because he was so drunk that night. Luann later appeared on The Steve Harvey Show (via The Daily Mail) and described the incident as "a bump in the road," and said, "I think that if you can't forgive somebody you love, who can you forgive?" That's sweet, but obviously that forgiveness even has its limits.

Just seven months into their marriage, Page Six reported that Luann slapped Tom during "a physical confrontation" at a "fancy Manhattan restaurant." Sources also told Page Six the pair had already "broken up and gotten back together a number of times" since being married, and that "it isn't exactly a match made in heaven."

Of course, Luann refuted the claim that she slapped Tom, telling Andy Cohen on an episode of Watch What Happens Live that they "have a very passionate love affair going," and that they "never go to bed angry," but if they do, when they wake up, they "make up." Okay. That live show aired July 19, 2017. Keep that date in mind.

On July 31, 2017 — 12 days after Luann's "passionate love affair" speech — Page Six reported that Tom was spotted flirting with a woman at a dive bar while Luann attended an event held by castmate Jill Zarin in The Hamptons. "An attractive blond woman at [famed dive bar] Murf's in Sag Harbor was seen getting a text from D'Agostino... one of her friends blurted out, 'That's her married ex-boyfriend Tom, who's still in love with her,'" an eyewitness told the gossip column. Tom then allegedly showed up 45 minutes later and tried cozying up to the woman, including "putting his hand over hers," although she reportedly rebuffed his advances.

Both Tom and Luann vehemently denied that anything inappropriate occurred, with Tom saying, "Luann knew where I was and who I was with. There is no story here." Less than a week later, Luann announced their divorce on Twitter.

On top of the fighting and alleged cheating, Tom has reportedly never been the marrying type. Sources told People, "Tom was 50 and had never been married," adding, "He never wanted to give up his bachelor lifestyle," which is a curious claim since he did agree to a marriage. Anyway, a source also told Page Six that Tom "hates the whole reality [TV] thing," and that "he doesn't want the attention or the scrutiny," which again, is odd since the man proposed to a woman who stars on a reality TV show. But perhaps there are other reasons for Tom's sudden aversion to his Bravo bride.

For now, we can only speculate on what caused the end of Tom D'Agostino and Luann de Lessep's marriage, but there's a good chance that an entire season of reality television is going to be devoted to at least Luann's side of the story. Side note: Anyone else wish they could get just a tiny peek at Sonja's DMs right now?