SINGAPORE: After nearly three years of helping her best friend with both money and job hunting, a woman shared on Reddit that she’s now unsure how to support her any further.
Opening up on the r/askSingapore forum on Saturday (Aug 9), the woman explained that when her best friend lost her job, she stepped in to help. She assisted with the job search, went through her resume to improve it, and even offered to speak to her own bosses to see if there were any suitable openings.
Working in the public sector herself, she also encouraged her best friend to take advantage of government initiatives like SkillsFuture and e2i.
Unfortunately, despite her efforts, nothing worked out. Her best friend also brushed off her suggestion about taking steps to upgrade her skills, choosing instead to “complain about how tough the job market is” and “blame the companies who didn’t hire her.”
She also noticed that in nearly three years of unemployment, her best friend had only submitted about “100 applications and attended 10 interviews.”
Over time, another issue began to weigh on her. The woman revealed that she, along with two other close friends, has been quietly covering her best friend’s expenses whenever they go out.
“When we go out, my best friend rarely pays for anything. In the beginning, she would still insist on paying her share, but we would always convince her to let us cover it.”
“After a while, she stopped offering altogether. When we travelled together last year, we paid for her hotel, transport, and meals too,” she wrote, adding that while these gestures were meant to help, they have now become an unspoken expectation.
The woman admitted she is beginning to question whether her friend is genuinely putting in the effort to find work or is simply in denial about her situation.
“It’s really sad to see her like this. I honestly don’t know how to help anymore. She still hasn’t found a job, and I know it’s affecting her relationships with her family and boyfriend, too. Sometimes I wonder if we should continue supporting her financially, but it feels weird to just stop now,” she wrote.
The woman also mentioned that when she brought up the financial issue with her close friends, they agreed that it had indeed “become a problem.” However, none of them had the heart to confront her.
“When I brought this up with my close friends, they agreed it’s a problem, but none of us really feel comfortable talking about it. Honestly, I feel conflicted and feel like a bad friend for posting this.”
Seeking advice, she asked the Reddit community, “How do I help my best friend?? Despite what’s happened in the past few years, she’s been a really dear friend and has helped me through some difficult heartbreaks.”
“Willingness to change has to come from her.”
In the comments, many Singaporean Redditors praised the woman for being such a caring and supportive friend, saying it’s rare for someone to stick by another through years of unemployment.
At the same time, they cautioned her about the risks of helping too much for too long, pointing out that it could eventually hurt her own finances, mental health, and even the friendship itself.
Several suggested that she set clear boundaries and have an open, honest talk with her friend about the situation, even if it feels awkward.
One Redditor wrote, “I suggest you sit her down and give it to her straight – let her know it’s not sustainable for y’all to be paying for her and that she needs to woman up and change her mindset or upskill. Sounds harsh but I believe that you have to be honest, because if not, you’ll enable this behaviour. If she’s worth her salt as your friend, she’ll eventually thank you.”
Another commented, “You and your friends have been enabling her lifestyle. Why? If y’all keep helping, your friend won’t feel the need to change. The best thing y’all can do is cut her off financially ASAP. Once your friend realises that her lifestyle is no longer subsidised, she will look for opportunities to earn to upkeep the lifestyle.”
A third remarked, “Paying for her is supporting her bad behaviour. Tough love is needed, as others have said. Now it is like she is rewarded for being jobless. Willingness to change has to come from her.”
In other news, a fresh graduate took to social media on Monday (Aug 4) to express his frustration with his job search, saying that many of the positions he is aiming for appear to have already been filled by foreigners
In an anonymous post on the r/singaporeraw subreddit, he shared that he has followed the conventional path diligently. He enrolled in one of Singapore’s top three universities, Nanyang Technological University (NTU), earned an engineering degree, did internships to build up experience, and graduated with Honours with Merit.
Read more: ‘Really buey tahan’: NTU graduate says job opportunities are going to foreigners
