When Mr Linus Li wanted to propose to his then-girlfriend back in 1994 he got the kiss-of-death rejection.
She only saw him as the brother type and said she had the hots for someone else.
Then 36, he figured it was because he looked average.
Two years later, after giving up on marriage, he dived into his new passion - perfecting his looks. Twenty years later and he's still at it.
Now 56, the senior sales executive from a premium airline is the oldest contestant ever to join Manhunt Singapore since the pageant's first outing in 1987.
Mr Li looks a good decade younger with his toned physique and easily gives the other younger contestants a run for their money.
This year, 16 finalists are competing in the junior category (below 30 years old) while Mr Li will go head to head against nine other hopefuls in the senior category.
This year's pageant finals will be held at local nightspot Neverland II on Sept 11.
Mr Li told The New Paper: "I haven't had a girlfriend (or gone on a date) in the last 20 years even though some women have been interested in me.
"To be honest, it's a burden having to take care of someone else. I told myself back in 1994 that if I didn't get married, I'll be content remaining single."
He added: "I remember I was going to propose to my girlfriend after dating her for a year and when I asked her about taking it to the next level, she told me she realised she only saw me as a brother and that I had got the wrong message (from her).
"So I thought, forget it. I'm not going to bother about marriage anymore.
"You see what I look like now, but the truth is that I didn't use to look like that. In fact, I didn't have money, I had nothing."
It was only after he decided to turn his life around in 1996 by adopting a healthy lifestyle that he scored his lucrative sales job a few years later.
Mr Li, who is 1.8m tall and used to weigh 83kg, now weighs 76kg thanks to his four-times-a-week workout which consists of a 1½ hour run and weight-training, focusing on his chest, shoulders and legs.
Even now, when he looks back on his past relationships, he can't help but feel guilt.
The irony was that Mr Li's first girlfriend, whom he dated when he was 21, was ready to take the plunge and walk down the aisle with him.
However, he wasn't in the frame of mind to get hitched then and he broke her heart by telling her the truth.