Rent Dilemma – When Love, Money, and Generosity Clash in Chicago

Handsome man counting cash

In the heart of downtown Chicago’s bustling streets, an intriguing story is unraveling – one that’s sparked passionate conversations among the online community. This narrative revolves around a young couple fresh out of college navigating the tricky terrain of shared expenses and parental generosity.

The original poster (OP), a 23-year-old woman, finds herself grappling with a situation that has polarized opinions and sparked debates across social media platforms. OP and her boyfriend, Jake, began their journey as college sweethearts. They shared not only their dreams but also their financial responsibilities, splitting rent, utilities, and groceries down the middle. However, as life took them from the campus to the urban jungle of Chicago, their story took an unexpected turn.

The twist in the tale comes from OP’s father, a well-to-do man in real estate who owns multiple investment properties. He graciously offered her a rent-free apartment in a ritzy downtown Chicago building from his portfolio. But there was a catch. OP’s father demanded that OP’s boyfriend, Jake, would have to pay a monthly rent of $400. OP’s father reasoned that he does not want OP’s boyfriend to stay with her just because of some free place to live. Rather, the father wanted OP’s boyfriend to be with OP for who she is.

OP shared that if the apartment was rented out to other tenants, the market rate would be a staggering $2,100 per month. However, when OP told her boyfriend that he would have to pay, it caused a rift in the relationship. Jake, who had been sharing rent with OP for the past two years, was suddenly faced with the prospect of paying $400 a month while OP enjoyed her father’s benevolence. Jake demanded that OP should share half the rent as they always do.

On the contrary, OP states that their rent in their college town was $1200, and her boyfriend used to pay $600. Now, OP shares that her boyfriend is getting a $200 discount as he would only have to pay $400 for an even nicer house.

With this as the background, OP turned to the online community to seek advice on whether her father’s decision to charge her boyfriend sounded wrong in any way.

Splitting Rent Fairly

The online community erupted with comments, each offering a different perspective on the situation.

One user, zadidoll, offered a creative solution, suggesting that if Jake insisted on splitting rent, they should do it based on the full market value. In this scenario, Jake’s share would be $1,050, a far cry from the discounted $400. This solution would ensure equity while respecting OP’s father’s intentions.

On the other hand, SlinkyMalinky20 pointed out that OP’s father might be trying to convey something about Jake through this arrangement.

“I think your dad might see something in your boyfriend that he’s hoping you will soon see.”

Such a sentiment, while speculative, adds an intriguing layer to the narrative.

OkeyDokey234, another user, highlighted a perspective that emphasized empathy and reciprocity.

“Your boyfriend needs to understand that it’s not that you aren’t paying rent. Just that your dad is paying your share. Put him in your shoes. If his parents covered his rent, would he be obligated to also cover half of your half?”

This angle invites readers to contemplate the dynamics of financial responsibility in a relationship.

Devlin94, however, took a firm stance in favor of OP’s father’s generosity. He suggested that Jake should be grateful for the opportunity and acknowledge the benevolence by willingly paying the $400 rent. This user’s comment underscored the importance of gratitude in relationships and how failing to appreciate such generosity can strain them.

However, Dazedkatwoman took a different position that goes against OP and her father. The user offered a nuanced perspective, addressing the underlying dynamics of the situation.

The user pointed out that the “test” seemed unwarranted, given that Jake had been contributing equally to their shared expenses in the past. The sudden change in the financial arrangement, driven by OP’s father’s role as a landlord, placed an unexpected burden on their relationship. The user also asked OP a question that was simple but profound: “Was Jake’s worth in the relationship measured by $200 a month?”

The Verdict

This story serves as a microcosm of the intricate web of love, money, and generosity that often entangles couples in today’s world. As the online community grapples with their differing opinions, the central question remains: Should love and commitment be quantified in monetary terms?

In OP and Jake’s situation, the lines between love, financial independence, and parental involvement are blurred. OP’s father’s actions, whether rooted in concern or testing, have sparked a conversation that resonates with many. The situation highlights the challenges couples face when navigating the transition from college life to the complexities of adulthood.

What do you think? Let us know in the comments. Do you think OP’s father from this social media post was wrong?

Featured Image Credit: Y-Boychenko /

This article was originally published on Ash & Pri.

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Pri Kingston

Ash & Pri are the Founders of and have spent the last decade building their way towards financial freedom and a lifetime of memories. Having successfully achieved their early retirement goal in under 10 years, they look forward to sharing their financial sense with like-minded people. Read more about Ash & Pri in the 'About Us' section.