Ines De Ramon and Brad Pitt’s Relationship Shows Some Clear Warning Signs

Though having a marriage in your past before finding The One isn’t necessarily a red flag, it can be a little eyebrow-raising if someone has had multiple weddings. While de Ramon was married to Paul Wesley (yes, “The Vampire Diaries”‘ Paul Wesley!) from 2019 until 2022, Pitt was famously wed to Jennifer Aniston from 2000 and 2005 and Angelina Jolie from 2014 until 2024 (though they split in 2016).

Although there are perfectly legitimate reasons for ending a marriage, someone who repeatedly finds themselves at the end of a wedding aisle may have deep, personal reasons for tying the knot so many times. In some cases, they may require therapy to better understand the desire to constantly make such a big commitment. “It could be that they may have an underlying mental health disorder, personality disorder, or attachment wounds that have left them feeling vulnerable — so they tend to fall into unhealthy relationship patterns,” psychologist Andrea Sartor suggested to Metro.

If Pitt has done the internal work to find out why his previous marriages failed and knows how to avoid the same pitfalls, things could work with de Ramon. If he hasn’t, that could be a red flag that he’s not learning from his past mistakes.

In September 2022, Ines de Ramon confirmed her separation from Paul Wesley after three years of marriage. A rep for the star told People, “The decision to separate is mutual and occurred five months ago. They request privacy at this time.” But it was only two months after the separation was announced that de Ramon was first spotted with Brad Pitt. A source told People, “[They] have been dating for a few months,” with another claiming, “It’s not an exclusive relationship.”

But the timing is potentially concerning, as de Ramon didn’t have much time to take stock of the demise of her marriage. Though there’s no standard formula for getting back into the dating game (“It is less about the amount of time that has passed and more about how much of the grieving and healing process you have worked through,” dating and relationship coach Nicole Haley exclusively tells Women.com while sharing her best tips for getting back into dating after divorce), a few months isn’t long to heal or get to know herself as a single woman again. As Jeannine Lee, author of “Beyond Divorce,” told Online Divorce, “Dating before you’ve completed the emotional business around your past relationship almost guarantees that you will choose the same kind of person you just left.” 

If de Ramon truly felt ready and in a healthy enough place mentally to get back out there, moving on quickly may not be a problem. However, if her romance with Pitt started as a rebound or she has unresolved feelings from her marriage, that could cause issues down the line.

Though Brad Pitt hasn’t publicly confirmed he’s been unfaithful, it’s hard to ignore the multiple cheating allegations against him. A source claimed to Page Six that Pitt supposedly had a wandering eye during his marriage to Angelina Jolie, purporting, “[Jolie] hired a private eye because she felt that he was fooling around … on the set, and it turns out, he was. And that was the final straw.” 

Of course, there was also speculation about how his relationship with Jolie first began, as they met during the filming of “Mr & Mrs Smith,” while he was still married to Jennifer Aniston. Aniston’s close friend and “Friends” co-star Courteney Cox spoke about the affair rumors to Vanity Fair, stating, “I don’t think [Pitt] started an affair physically, but I think he was attracted to [Jolie]. There was a connection, and he was honest about that with Jen … It was an attraction that he fought for a period of time.”

Though Pitt hasn’t been publicly accused of stepping out on Ines de Ramon, if there’s any truth to the past cheating rumors, it’s no green flag. Kalley Hartman, LMFT at Ocean Recovery, exclusively shares advice for trusting someone who has cheated before with us. To ensure de Ramon doesn’t develop trust issues with Pitt, using Hartman’s advice, the two should discuss his past to understand why he may have cheated. “Ask them to share more details, such as when the infidelity occurred, how they responded to it, and what steps have been taken since then to ensure that it won’t happen again,” Hartman suggests for couples in a similar situations. “This can help you gain insight into both their thought processes and actions regarding the cheating behavior.”

Though Brad Pitt and Ines de Ramon haven’t publicly confirmed an engagement, a source told InTouch they supposedly want to walk down the aisle — if they can get on the same page about a prenup, that is. Though Pitt’s rep denied he was thinking marriage with de Ramon, a source told the outlet in early 2025, “The wedding is on hold. The main reason is that she’s refusing to sign a prenup. Ines doesn’t want to totally sign away her rights. It’s become a touchy subject for both of them.” The insider continued, referring to the eight-year legal drama to finalized his divorce from Angelina Jolie, “Brad knows a prenup is necessary to move forward with Ines, but he isn’t in a place where he wants to deal with any more legal back-and-forth.” Considering Celebrity Net Worth lists Pitt’s net worth at $400 million and Money Inc puts de Ramon’s closer to $2 million, it’s understandable why the “Moneyball” star would want to protect his assets.

A prenup can positively impact a marriage but it can also be a dealbreaker if two people have totally different perspectives on it, and that could be seriously detrimental to their relationship. “Even if you’re madly in love, [if your partner] refuses to consider a marriage contract, that may be a red flag worth paying attention to,” lawyer Elena Hoffstein told Women of Influence. If de Ramon really is set on not signing on the dotted line, it’s imperative the two discuss why and come to a mutually beneficial conclusion with a full understanding of the other’s perspectives.