Man who pays for everything wonders why he can’t fully love his successful, drama-free girlfriend
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SINGAPORE: A 31-year-old Singaporean shared on social media that even though his girlfriend looks like the “brightest green flag” on paper, he still feels strangely disconnected and unsatisfied in the relationship.
Detailing his situation on Reddit’s r/sgdatingscene forum, he explained that his 28-year-old girlfriend ticks every box most men would dream of: she has a successful career in finance, is sweet, kind, respectful, drama-free, and, most importantly, deeply in love with him.
To everyone else, she sounds like the perfect partner, but to him, it doesn’t feel that way.
He said the relationship often feels like a one-man show. “I plan all our dates. When she wants to travel, I pay for everything—flights, accommodations, and planned itineraries.”
“When she has challenges at work, we fire up her Excel models on the monitor, and we work through stuff together. She regularly leans on me for advice on doing better at her job. When she has worries about finances, I work out numbers with her to reassure her.”
Knowing she comes from a broken family, he also constantly reassures her that his parents would welcome her with open arms once they marry.
However, when it comes to his own needs, he feels like the effort isn’t reciprocated. “I’m a very adventurous person who has lots of hobbies. I’ve tried many times, gently nudging her to pick up a sport that we can do together, even offering to pay—but she always feels like I’m pressuring her. So I’ve stopped raising it.”
“She’s so passively low-maintenance that I don’t feel connected or that we share any real interests. I’m tired of always asking for more, but at the same time, I feel incredibly guilty,” he said.
Confused about his own feelings, he ended his post with a big question: “If she’s great at everything else, why can’t I just love her for who she is, instead of trying to change her into someone she’s not?”
“Unless she genuinely wants to step up, this will keep feeling lopsided.”
In the comments, many pointed out that just because his girlfriend embodies what most would consider a “green flag” does not mean she is automatically the right partner for him.
They explained that relationships are not about ticking boxes on a checklist. A person can be accomplished, kind, and drama-free, yet if there is no sense of connection or fulfilment, the relationship will eventually feel hollow.
Several also suggested that the heart of the problem may lie in their “differing love languages.” To her, having a partner who plans every date, arranges trips, offers career support, and reassures her about family concerns might be more than enough.
These acts likely reassure her and meet her emotional needs, but for him, love seems to be expressed through shared effort, mutual care, and active engagement and those, the users pointed out, are not being reciprocated.
“This is not a partnership built on mutual investment. This is you doing the heavy lifting emotionally and logistically,” one said. “Unless she genuinely wants to step up, this will keep feeling lopsided.”
Another added, “I think your need for a loving relationship is not met by her actions. It may seem fine for now, but when the relationship gets long and all, I think you will get sick and tired of who she is. Please rethink to see if she’s the person that you want to wake up to every day.”
Some also advised the man to have an “honest conversation” with his girlfriend rather than quietly carrying the weight of his frustrations
One commented, “I think what you want from her is proactiveness, right? I can definitely understand that, as I’ve been in your shoes before. Have her understand that she needs to proactively do her part in taking actions and also putting in effort for her to plan and decide as well.”
“She shouldn’t be sitting all day long waiting for you to do everything for her. It’s a continuous team effort to support each other both ways.”
In other news, an employee turned to Reddit for advice after his manager crossed a major line by contacting his mother during his hospitalisation leave over a so-called “non-obligatory company survey.”
“I’m really pissed off. It’s nothing urgent, and I don’t see the need to get my family involved for a voluntary survey. I don’t even know how he got my mother’s contact number.”