A "tormenting" decision to ditch his bride-to-be may still haunt Massimiliano Allegri, but as the Champions League quarter-finals loom the Juventus coach should be more than ready for his next life-changing decision.
A talented midfielder who ultimately failed to reach the heights in Serie A, Allegri is set to steer the Turin giants into the last eight following a 2-0 last 16, first-leg win at Porto.
It would be his third such feat, having steered Juve to the 2015 final when a chastening 3-1 defeat to Barcelona capped a solid first year in charge of Italy's biggest club and taken AC Milan to the last eight and elimination by Barcelona in 2012.
After seeing Barcelona overturn a 4-0 first leg deficit to Paris Saint-Germain to qualify last week, Allegri is taking nothing for granted.
"Barcelona are now favourites to win the Champions League, along with Bayern Munich and Real Madrid," he said.
"More importantly, it shows that, despite us having a two-goal lead, it's not over yet."
Now boasting three Serie A titles from spells at AC Milan (2011) and Juventus (2015, 2016), and still in contention for a third successive league and Cup double, Allegri has little to prove in Italy.
And with a triple passion for the sea, horseracing and football, a purported move to England -- where he is tipped to replace Arsene Wenger at Arsenal -- seems to be edging closer for the Livorno-born coach.
Had Allegri decided otherwise two days before he was supposed to marry his then fiancee Erika in June 1992, his life might have taken a different direction.
The flowers had been delivered to the church when Allegri stunned his bride-to-be with a last-gasp change of heart in June 1992.
Years later, he explained: "It was me who made the decision after tormenting myself for months about it.
"I had a three-metre high wall in front of me. In these situations, you have two choices: try to climb over it, or go back the way you came. I turned around, and disappeared for a while."
- Arsenal watching? -
A promising midfielder with newly-promoted Pescara, Italian media reports at the time described how Allegri had "dribbled his way around everybody".
But the Capuchin monk who thought it was a "joke" when Allegri's father called to cancel the wedding offers a glimpse of Allegri's penchant for going on instinct.
"Not every cloud has a silver lining," Ermenegildo said in an interview with Corriere della Sera on June 30, 1992. "It was better now than later."
His ex-fiancee's family are unlikely to agree, but swapping wedding vows for a commitment to the beautiful game has paid dividends.
Despite spending the bulk of his career moving up and down Italy's top flight with smaller clubs like Perugia and Pescara, Allegri has never lacked self-belief.
Nicknamed 'Acciuga' (Anchovy) due to his coastal origins, and a lithe physique that "enabled him to "wriggle" through opposition defences, Allegri is particularly appreciated by mentor and former coach Giovanni Galeone.
"He walked in on his tiptoes, but quickly led the dressing room," Galeone said in a 2015 interview with goal.com. "We'd signed a great player who was focused, and respectful."
Scoring 12 goals from midfield in 32 appearances for Pescara the season after he decided not to marry was Allegri's finest in Italy's top flight.
When it ended in 2003, he worked through the ranks before leading Sassuolo into Serie B in 2008.
After a two-year spell at Cagliari, a move to AC Milan in 2010 saw Allegri end the Rossoneri's seven-year wait for the scudetto in his first season in charge.
When in 2013 Milan sold a batch of big stars including Zlatan Ibrahimovic and Thiago Silva, Allegri lost the spine of the team he had steered to a last eight clash with Barcelona in 2012.
Sacked in January 2014, ironically following a 4-3 San Siro reverse to Sassuolo after Milan had led 3-0, the seven-time European champions must now be regretting their decision.
As Milan continue to struggle to even qualify for Europe, Allegri will be looking confidently towards the Champions League quarter-final draw in Nyon, Switzerland on Friday.
Arsenal, if reports are to be believed, will be watching too.