They braved criticism when word spread early last year that they were dating.
Netizens labelled her a cradle-snatcher and him, her toy boy.
Local radio DJ Rosalyn Lee, 36, and Justin Vanderstraaten, 24, a business student at Singapore Institute of Management (SIM), eventually won some of their detractors over by being non-apologetic for their 12-year age gap.
People who have come to support this couple were shocked two days ago after Lee posted on her Instagram account that they had broken up after almost two years together.
The host of TV home makeover series RenovAID, who declined to be interviewed, explained in her Instagram post why she finally broke her silence.
She felt that not saying anything about her break-up was hypocritical, especially when she has received a lot of love and support from fans.
Wrote Lee: "We've (Justin and I) been on the rocks since May this year but have been trying to make things work. We tried up till mid-September this year but to no avail.
"I'd like to believe its (sic) NOT our 12-year age gap that (did us in). We were so fine all of last year. We were a team. It was us against the world."
The reason she cited for the break-up? Insecurity.
Lee wrote: "I guess (Justin) being with me got too overwhelming and insecurity eventually crept in, took over, and won the battle."
She said that a part of her feels resentment that she and Mr Vanderstraaten had lost what they used to have, but she is feeling better by the day.
NO THIRD PARTY
Lee clarified that there was no third party involved in their break-up. Neither did they "fall out of love" with each other.
Even though she has bitten the bullet and announced her break-up, it was not easy.
She said that sharing a painful break-up is not anything like sharing the happy times in a relationship.
But she made it clear that she had no hard feelings towards her ex.
"I believe great things will happen for this guy, and lucky is the girl who gets to date him next.
"These are my final words about the relationship, I will not be elaborating on this any more from here on.
"I have chosen my favourite photo of us for this post because this is how I would like to remember us: once solid and happy together."
Fans of Lee and Mr Vanderstraaten were rooting for them, especially after Lee told TNP in an interview in February that she was open to marriage after meeting him.
Lee, who used to date local celebrity photographer Kevin Ou, said in the same interview: "Before this (meeting Justin), I was against marriage and having children because marriage doesn't guarantee forever.
"I never thought of it as something I needed to go through to stay in love with someone.
"But now I want to keep it open and if that is where we are headed and if it feels right, let's do it."
In the interview, Mr Vanderstraaten said he felt Lee was the one for him.
"I don't think you should be with someone if you don't see a future with her," he said.
Lee also said at the time that their age gap was initially a problem, but Mr Vanderstraaten had put in effort to help mitigate it.
"There was a trial-and-error process at the beginning because we might not have got each other when we argued," she said.
"But the thing about Justin is when you explain to him once, he learns and does not repeat it."
See also: S'pore DJ calls dead mum's phone as she misses her
AGE GAPS ARE CHALLENGING: EXPERTS
Couples with a big age gap face unique challenges on top of what ordinary couples normally face, dating and relationship experts tell The New Paper.
Ms Violet Lim, CEO of LunchClick and co-founder of Lunch Actually said that older women may find their partners immature. Conversely, their partners may find them naggy.
"If the female is much older than the male, there might also be a tendency to 'mother' him," she said. "And that might be suffocating for the male and the female might eventually lose respect for him."
Another challenge could be financial,as when the woman is more advanced in her career. "The male's ego might be hurt," said Ms Lim. If a woman is older than the man, she may feel insecure about her looks and this may create issues for the relationship.
There are additional pressures if one of the partners is a celebrity.
In this case, the celebrity in the relationship needs to be understanding and sensitive to his or her non-celebrity partner's needs, said Ms Lim.
The celebrity should not assume that his or her non-celebrity partner can deal with the same situations as well as him or her, she added.
The non-celebrity partner must be confident and self-assured enough to not feel threatened or intimidated by his or her celebrity partner.
Ms Jenny Ng, director of Dating Moments, said that in her experience with couples where the woman is older than the man, the woman may find it hard to mingle with her partner's social circle due to the age gap.
So how does one mitigate such challenges?
Ms Elyse-Anne Lim, CEO of Elyse-Anne International, said that she believes that finding the "sweet spot for communication" is key to making such a relationship work.
She said that couples who have insecurities should use whatever form of communication they are comfortable with to voice their discomforts.
This can take the form of e-mail, SMSes and phone calls, if they feel awkward talking about it face-to-face.
Ms Michelle Goh, owner of CompleteMe, believes that harnessing one's sense of empathy is key to solving relationship problems.
"Always place yourself in the other party's shoes," she said.
See also: DJ Rosalyn Lee's debut acting role confront issues with estranged father
This article was first published on Nov 12, 2015.
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