‘I’m struggling at work’: Singapore man asks how to navigate relationship with wealthier woman

SINGAPORE: A man turned to Reddit to ask how to handle a new relationship with a woman who is more successful and financially secure than he is.

In a post on the r/asksg subreddit on Monday (Sep 14), he explained that he had matched with the woman on a dating app. She is 12 years his senior, well established in her career, financially comfortable, and has teenage children.

He, on the other hand, is in his mid-30s, owns neither a home nor significant assets, and is battling severe work anxiety in a job he is barely managing to keep. He also admits he is not savvy about investing.

Though he describes her as genuinely kind, he confessed to feeling “stressed about the massive imbalance.”

“She has far more relationship experience than I do. More importantly, I’m worried she might just be looking to be pampered on dates. If I try to keep up financially, it will completely drain the income I desperately need to save for foundational things like housing or investments,” he explained.

Unsure how to proceed, he asked: “Has anyone ever been in a relationship with this kind of dynamic? How did it work out for you, and how did you navigate the financial and experience gap?”

‘She’s dating you for you’

In the discussion thread, one commenter advised him to drop the gender expectations altogether.

“You need to remove the whole gender expectation thing from this equation. If she doesn’t have a problem with you, why do you have a problem with you?”

Another asked him, “Did she say she wants to be pampered, or is this your own thinking? I would find it odd that someone way older and established would be looking for that from a younger guy. Chances are she's looking for the emotional value you can bring.”

A third shared her own perspective, “As a married woman with children in my 30s with an established career, I can tell you that wanting to be pampered for ME means: Having my husband do things for me just because he knows I like certain things; Having my husband cuddle with me and compliment me with sweet nothings; Having time off from the kids.” 

“None of the above requires money, and if anything, I can supply the money since I have it.”

A fourth reassured him that she isn't dating him for his material wealth or achievements, but for who he is. 

“She’s dating you for you. Don’t think so much as long as you enjoy the relationship.”/TISG

Read also: ‘No one goes until at least 10’: Singapore intern struggles with 13-14 hour workdays