Titled Jay on the Hay, it was reported that the twins started the blog to share their thoughts and feelings as they didn’t have many friends in secondary school. The twins also have a YouTube channel by the same name, which has three videos of which two are song covers.

After much persuasion by Hayley Woo, Jayley Woo accompanied her sister to partake in The New Paper New Face modelling competition in 2011. In the end, Jayley went through to the final round and later scored a role in the school drama Jump! Skip With Us (2002). They later starred together in their debut movie That Girl In Pinafore (2013) as twin sisters in sync.

Jayley and Hayley Woo expressed ambitions to expand overseas in 2018 and 2020 respectively. Jayley Woo expressed the sentiment after she departed Mediacorp as a full-time artist and said that her newfound flexibility would allow her to explore overseas opportunities. Similarly, Hayley Woo took acting courses in Shanghai and learnt a lot about how the Chinese entertainment business.

In January 2019, news broke that fellow actor Aloysius Pang succumbed to injuries sustained while on reservist in New Zealand. It was later revealed that Aloysius Pang and Jayley Woo had been dating for a while and his death left her heartbroken and depressed for a long time.

“I felt like maybe I was cursed, and that’s why my partner died. For a while, I blamed myself. I felt like I wasn’t worthy of love. My parents told me I had to stop thinking that way because that negativity wasn’t affecting just me, but people around me too. So I tried my best to work on myself and my mental health.”

In October 2022, Jayley Woo revealed that she was engaged and pregnant. She had been dating her fiance, whose surname is Tan, for close to a year and he proposed “in the first half of 2o22”. Tan works behind the scenes in showbiz and fellow actor Julie Tan introduced the two. The couple is also planning a wedding on December 27.

The twins opened up to 8days in 2017 that Hayley Woo had experienced being hit on multiple times while the two were working in South Korea. In one instance, Hayley Woo tried to rebuke the guy by saying that she had a boyfriend but he grabbed her arm and she shouted “Don’t touch me!” to scare him off finally.

Ever since Jayley Woo started blogging in 2005, she has been on the receiving end of many sexual harassments. “I would check my Instagram inbox while I eat and be appalled by what I was seeing. Why do they (the different men who have sent her these pictures) have the courage to send me such explicit content?”

Jayley Woo would also receive “social escort” offers from people who are willing to pay for her time. The harassment only got worst after she became a celebrity. Despite this, she stated that she didn’t want to take action against them as she “believes that ignoring their messages is the best way to deal with them”.

In 2018, Jayley Woo shared that she was a victim of bullying when she was in secondary school. “As the class representative, my classmates hated me whenever I told on them to the teachers. All I wanted to do every day was to hide in one corner in school.”

She later found confidence through her Institute of Technical Education (ITE) friends and also through blogging with her sister Hayley Woo (see point #1).

After getting her Covid-19 booster shot in January 2022, Hayley Woo suffered from chest tightness, breathing difficulties, blurry vision and even blacked out for five minutes. It was a wake-up call for her as she was informed to have low blood pressure, low red blood cells, malnutrition, dehydration and was underweight and lacked iron and calcium. Hayley Woo later reflected, “I think it really is a silver lining to warn me to eat healthily and exercise, and that I cannot keep up this lifestyle.”