Ben Affleck reportedly regrets breaking up with this ex
Did those Tom Cruise pictures bother him? It certainly sounds like it…
Words by Nikki Peach

We’ve all indulged in Ben Affleck’s love life more than we care to admit – especially in the past year. Even if you didn’t want to know which ex he’s rumoured to be getting back together with, or which Jennifer he has ‘regrets’ about, stories about Affleck and his romantic capers are almost impossible to avoid.
The best part of last year was dominated by ‘will-they-won’t-they’ divorce questions surrounding his marriage with Jennifer Lopez, who, somewhat confusingly, he first dated between 2002 and 2004 and then rekindled with in 2021 before marrying in 2022. The answer was ‘they will’ and Lopez filed for divorce on 20 August, citing April as the month they officially separated.
Confirmation of his divorce gave way for new rumours that Affleck wanted to give things another go with his original ex-wife, Jennifer Garner, who he was married to between 2005 and 2018 and shares three children with. Garner has been a source of comfort and support throughout his second divorce and the exes are often pictured together with and without their children where Affleck looks noticeably less miserable than he did on the red carpet with Lopez. This year Garner and Affleck cannot so much as walk down the street without a flurry of stories about their impending reunion.
While the ‘Bennifer’ divorce rumours were true, it’s more than likely that the Garner reunion rumours are being fueled by social media users who love the drama of it all. An insider has since confirmed that the two stars have ‘no intention’ of getting back together.
Now, to make matters even more complicated, new ‘sources’ have introduced a third ex-girlfriend into the equation and claim Affleck wishes he could go back in time and work things out with Ana de Armas. Affleck and de Armas dated from 2019 to 2021 after meeting on the set of Deep Water and apparently broke up because ‘she wanted marriage, and he did not’.
De Armas has recently been in the headlines after being spotted at a London Heliport with Tom Cruise. The pair are said to be preparing for an undisclosed project with director Doug Liman, but a series of photos of them laughing and smiling together have also sparked rumours that they might be dating. However, another source has since confirmed to People that the rumours are not true.
‘He wishes he could go back and do things differently’
Even so, seeing de Armas laughing and smiling with another Hollywood stalwart – one with a dating history arguably just as messy as Affleck’s – has reportedly prompted pangs of regret in the Argo star. A source told the Daily Mail, ‘Ben and Ana had such a special and unique relationship because they were holed up together 24/7 during the pandemic. They got so close so fast, and it was passionate and real.’
Of course, despite struggling to commit to de Armas, Affleck went on to marry Lopez a year after they broke up. ‘In hindsight, he realises how wrong this was and sees that he could have dodged the JLo bullet by not ending things with Ana,’ the source adds. ‘He knows how she must have felt.’
The insider went as far as to suggest that Affleck ‘wishes he could go back and do it differently’ but knows he can’t. ‘He hopes she finds what she wants and has a family. He thinks she is an incredible woman.’ Who knew dismounting a helicopter with Tom Cruise could elicit such a reaction?
Apparently, it wasn’t just marriage that posed an obstacle for Affleck and de Armas, either. He was also unwilling to commit to having more children and since de Armas is in her 30s it was a deal breaker. ‘They have had numerous discussions about their future, and they decided together to break up,’ a source told Page Six at the time.
It’s a classic trope that when a relationship ends, people harp back to the person who came before and wonder if they were right for them all along. Often this is a result of lingering attachment anxieties, unanswered questions or a longing to feel close and familiar with someone other than your most recent ex. In Affleck’s case, it seems like a medical affliction.
Of course, it’s another classic trope to feel jealous or regretful after seeing pictures of your ex looking happy with someone else. As the poster boy for ‘resting divorce face’ during his marriage to Lopez, and a literal brand ambassador for Dunkin’ Donuts after being picture eating so many of them during his divorce from Garner, Affleck is nothing if not committed to the stereotype.
It wouldn’t hurt for him to realise that there are approximately four billion women in the world – most of whom he has not dated and does not have pre-existing baggage with. Many of them aren’t called Jennifer either. Perhaps Affleck would be better off giving one of them a call instead.
Photo: IMAGO