Matt Damon shares complicated relationship with Jennifer Lopez amid best friend Ben Affleck's divorce

LOS ANGELES, CALIFORNIA: Singer/actress Jennifer Lopez and actor Matt Damon share a strong connection despite her divorce from his best friend, Ben Affleck.

Damon was spotted holding Lopez's hand during a private talk at the Toronto International Film Festival amid the 'Jenny From the Block' singer's ongoing divorce from Affleck.

It was previously reported that during the TIFF afterparty at the Ritz-Carlton's EPOCH Bar & Kitchen Terrace, Lopez and Damon had a "long, deep conversation."

Matt Damon shares complicated relationship with Jennifer Lopez amid Ben Affleck divorce

Friends being forced to take sides is one of the many negative aspects of divorce, thus it should come as no surprise that the most famous separation of the year involves a host of issues and conflicting allegiances.

Matt Damon and Jennifer Lopez would have had a lot to catch up on when they were seen engaged in discussion at the 'Unstoppable' afterparty at the Toronto International Film Festival this past weekend.

The 'Hustlers' star, 55, and the 'Martian' actor, 53, shared a private moment on a couch during TTIF while holding hands.

In one of the pictures, Damon was seen nodding his head while listening to Lopez talk, while in another, the two had nice eye contact and seemed to be smiling at one another.

Images showing Lopez holding Damon's hand during their deep conversation surfaced a few weeks after the 'Jenny From the Block' hitmaker filed for divorce from Affleck—her husband of two years and Damon's best friend.

While Affleck's team called his ex-wife fame-obsessed and disliked their relationship being so public, Lopez's side claimed Affleck was "selfish, sullen and a loudmouth."

While expressing his unwavering commitment to "always have Ben's back," Damon's presence at the film festival was notable since Affleck chose not to attend, risking a highly public run-in with his estranged wife on the Toronto red carpet.

Regardless of the facts, the 'Good Will Hunting' star is arguably the best suited to provide some perspective, as he is the only person close to both parties who has supported them for their entire relationship—which has included a broken engagement, multiple marriages to different people, a reunion, and now a divorce.

Although 'The Talented Mr Ripley' star has publicly expressed his fondness for Lopez, he apparently confided in his best friend about his concerns regarding their compatibility.

Affleck was reportedly told by Damon to "focus on his work" and not lose sight of his career objectives before the announcement of their divorce.

"Matt tried to warn Ben when he got back together with JLo that this could happen," a source revealed to Daily Mail.

"Matt was there to help Ben get it together after their first split and he felt like this would happen again," the source added.

Matt Damon gets into awkward position amid Jennifer Lopez and Ben Affleck divorce

Matt Damon hasn't always been all that complimentary of his best friend's partner, which adds to the potentially awkward situation of being thrust into close quarters with his best friend and professional partner.

Affleck appreciates the opinions of his friends because Damon and his wife Luciana Barroso have had a happy marriage for more than 18 years.

The insider said, "Matt has had a successful marriage for years and Ben has always been in awe of this. As things started falling apart, Matt told Ben that he supports whatever choice he makes but wants him to jump in and focus on his work."

"Ben spent so much time focusing on JLo's projects just like he did the first time around. He told Ben, 'What has she ever done for your career?'," the source added.

However, this was different from what the 'Good Will Hunting' actor publicly said earlier when there were rumors that Bennifer was getting back together.

During a 2021 visit to the TODAY show, Damon was questioned about rumors that Affleck and Lopez were rekindling their romance, nearly two decades after their initial breakup.

Being tactful but encouraging, Damon told co-hosts Hoda Kotb and Savannah Guthrie, "There's not enough liquor in the world for you to get me to say something about that [rumor]."

However, once the rumor turned to confirmed news, Damon remained incredibly supportive of his best friend and exclaimed, "He’s the best. He deserves every happiness in the world. I’m glad for both of them."