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Home Lifestyle Fashion

Why Every City Feels Like the Worst Place to Find Love (According to Singles)

October 7, 2025
in Fashion
Reading Time: 6 min
Issa Rae, wearing an Orange Creamsicle-colored shift, talking to Kendrick Sampson, wearing a striped button-up over a T-shirt.
Issa Rae, self-confessed architect of a fantasy version of Los Angeles. Credit: Merie Wallace/HBO

Years after her hit HBO series ‘Insecure’ wrapped, creator Issa Rae confessed a surprising truth: she doesn’t actually think Los Angeles is a great city for dating. In fact, she admitted to intentionally romanticizing it for the show’s narrative.

From 2016 to 2021, ‘Insecure’ presented a vibrant Los Angeles, brimming with attractive and successful men of color vying for the attention of its Black female protagonists. The cast featured series regulars like Jay Ellis, Kendrick Sampson, and Alexander Hodge, alongside guest appearances from stars such as rapper Aminé and actor Sterling K. Brown.

“I felt like I was deceiving people,” Rae candidly shared in a recent interview, offering a stark contrast to the show’s glossy portrayal. “This is what I *wanted* it to be, but the reality is, it’s not.”

Television and film undeniably shape how we view cities, influencing everything from career choices to dating expectations. Think of how many have flocked to New York, inspired by its romanticized image in shows like ‘Sex and the City.’ Yet, a city’s dating reputation isn’t solely crafted by Hollywood. It’s often a blend of demographics, prevailing stereotypes, local gossip, and sometimes, plain common sense. For instance, singles in Seattle are said to have an abundance of eligible tech professionals, while those in Washington, D.C., are often advised to embrace dating within political circles.

So, how much truth lies in these sweeping urban dating generalizations? Some, perhaps. But one thing is clear: most people genuinely believe their own city is the toughest place to find love. And for some Black women navigating the dating landscape, these reputations can indeed influence significant life decisions.

Nia Randall, a 40-year-old, spent a dozen years in Los Angeles, initially drawn by dreams of the entertainment industry. She wasn’t directly influenced by ‘Insecure,’ but she was genuinely shocked by the difficulty of establishing a lasting relationship in the city.

“Dating there was incredibly challenging,” she recounted. “It’s honestly one of the main reasons I decided to move back to Chicago.”

According to Ms. Randall, the constant presence of celebrities and influencers creates a fiercely competitive dating environment. She vividly remembers an evening in 2013 when, out with friends in Hollywood, they were invited to join some men at their club section. She attempted polite conversation with one of them, but his interest quickly waned.

“I think he expected me to be more… amenable, clearly looking for something casual,” she explained. “I was genuinely just trying to have a conversation, and he actually told security to remove me.”

The security guard relayed the man’s message: “He said he wants different girls up here. You’re asking too many questions.”

Even when Ms. Randall, a content marketing manager, finally found someone she was seriously dating, the relationship was short-lived.

“He was an artist from Atlanta,” she shared. “We were incredibly smitten with each other.” But just a few months in, he delivered a shock: “He told me, ‘I want you to meet my other partner.’ I was absolutely stunned.”

Lailaa Robinson, a 37-year-old entrepreneur dividing her time between Georgia and Chicago, didn’t mince words when asked about dating in Atlanta. Her one-word assessment: “Scary.”

While her reasons weren’t exclusively unique to Atlanta, they were significant enough to sour her experience. She found many men she encountered lacked depth and were reluctant to commit to settling down or starting families, even as they approached middle age.

“Honestly, I believe I could find a more serious relationship in Chicago than in Atlanta if I made more of an effort there,” Ms. Robinson mused. “Chicago men seem to possess a certain sophistication, often being more business-oriented and working in finance.” This highlights how personal experiences can shape—or even create—a city’s dating reputation.

One of her Atlanta dating stories included a man who disclosed he was a former “porn star,” assuring her he’d left that life behind. Yet, a quick glance at his social media after the date revealed recent explicit content, posted just days before their dinner.

Often, a city’s dating reputation boils down to raw numbers: bigger populations might offer more choices, but demographic imbalances can heavily skew the playing field. For example, Seattle faces one of the most significant gender disparities among major U.S. cities. A January report cited recent census data revealing 120.5 unmarried men under 45 for every 100 unmarried women in the same age bracket in Seattle. This made it the fourth-highest male-to-female ratio among the 50 largest U.S. cities by population.

With such a demographic advantage, women in Seattle can afford to be more discerning. This stands in stark contrast to Washington, D.C., where a 2023 U.S. Census Bureau report indicated roughly 80 single men for every 100 single women.

For Deijza Curtis, a 28-year-old oral surgeon’s receptionist, dating in Denver has been somewhat simpler over the past two years, largely because her love for the outdoors aligns with the local culture. She’s grown accustomed to very specific types of invitations.

“It’s always, ‘Will you join me for a three-hour hike in the mountains?’ or ‘How about a ski-resort trip?’” she laughed. “Those are pretty much the only common interests I seem to share with people here.”

Despite this, she still describes her overall dating experience in Denver as ‘horrible.’

Perhaps this is the universal truth of dating: if your romantic life isn’t thriving, it’s almost instinctual to lay at least some of the blame squarely on the city you call home.

Share your dating thoughts, stories and tips with us. We’d love to hear from you!

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