Tiger Woods and Vanessa Trump's Relationship Timeline: Inside the 'Ultimatum' After Florida DUI Arrest

Vanessa Trump has stood by Tiger Woods since 2024, but his recent Florida DUI arrest and rollover crash in March have placed their relationship under intense strain. Despite the turmoil, the 48-year-old mother of five is reportedly staying, though not without conditions, as questions grow over whether the golf legend is ready to change.

Here is the reported ultimatum Vanessa has given Woods to prove he is willing to 'work on himself' before she commits for the long term, as the golfer decides to 'step away.'

Tiger Woods and Vanessa Trump's Relationship Timeline

Woods and Vanessa reportedly began dating around Thanksgiving 2024. Since then, they have remained together through thick and thin, including the golfer's recent car accident and arrest in Florida. The romance was sparked by their shared connection to the Florida junior golf circuit, where their children, Woods' son Charlie and Vanessa's daughter Kai, compete.

The romance remained a well-kept secret through the early months of 2025. It wasn't until March 2025 that the pair was spotted together at a TGL match, eventually leading Woods to confirm the relationship on Instagram with a post declaring that 'life is better' with Vanessa by his side.

Insiders say that the 50-year-old golf champion was ready to pop the question back in June 2025, just seven months after the two began dating. But for now, an engagement, or even moving in together, which was once reportedly imminent, seems out of the question due to the accident.

Tiger Woods' Florida Rollover Accident and DUI Arrest

On 27 March, the golfer was involved in an accident on Beach Road, where his Land Rover crashed and rolled over. Woods attempted to overtake a pressure-cleaning truck while driving at high speed, and his vehicle clipped the truck's trailer. Reports say that he managed to crawl out of the passenger-side window uninjured.

He was arrested for DUI and was held in custody for eight hours before being released on bail.

Official police report stated that Woods appeared 'lethargic and slow,' was 'sweating profusely,' and that his eyes were 'bloodshot and glassy' with extremely dilated pupils. He was also 'hiccuping' while speaking at the scene.

Woods passed a breathalyser test but refused a urinalysis for other substances and answered, 'I take a few,' when asked about prescription medication. Woods also told officers that he was looking down at his phone just to change radio stations.

Golfer Announced 'I Am Stepping Away'

Following the rollover crash and arrest, Woods announced that he is 'stepping away for a period of time' to focus on his health and to seek treatment.

On social media, he wrote: 'I know and understand the seriousness of the situation I find myself today.'

He added, 'I am stepping away for a period of time to seek treatment and focus on my health. This is necessary in order for me to prioritize my well-being and work towards lasting recovery.'

He said that he is 'committed to taking the time needed to return in a healthier, stronger, and more focused place, both personally and professionally.'

'I appreciate your understanding and support, and ask for privacy for my family, loved ones, and myself at this time,' Woods ended his statement.

The Relationship 'Ultimatum'

As reported by Star, Vanessa 'loves Tiger dearly, but this incident has freaked her out and forced her to reevaluate the relationship,' says an insider.

The incident served as a wake-up call, leading to a high-stakes ultimatum: Woods must commit to professional treatment or risk losing her for good.

Vanessa has been explicit about her expectations, as per Metro, she laid out specific, non-negotiable criteria for his recovery.

'This has to be a real rehab: doctors, counselors. It's pain management gone awry... so this has to be doctor-supervised,' th

The source continued: 'But she set a hard line: Fix this, and fix it permanently. She's not like other girlfriends.' They added, 'She required it and it was non-negotiable. And he loves her and wants to be with her, so he is willing to do it.' They also claimed Vanessa only gave Woods 'one chance.'