Relationships in the spotlight are rarely simple, especially when there's a significant age gap. In the late 2000s, the media couldn't stop talking about Katie Couric and her younger boyfriend, Brooks Perlin. This story dives deep into the details that many missed during the height of the "Katie Cougar" headlines.

Katie Couric, the veteran news anchor, might have found a story closer to home than the "CBS Evening News" desk. Her relationship with Brooks Perlin became a focal point for tabloid scrutiny, often overshadowing her professional achievements. For more on navigating age gaps, check out our guide on how to handle dating someone younger.

Perlin, 33 - whom Couric, 50, snagged at a Louis Licari salon event last fall and has been running around with since - seems to have a hard time settling down in a career as well as having a “pattern” of dating older women, a source says. It's one of those celebrity relationships that shocked the world at the time.

Not only has Perlin worked for three Connecticut-based hedge funds in the last five years, he hasn’t had a full-time job since September, a source told the Post’s Marianne Garvey. His professional life seemed as unsettled as his dating history, leading to many questions about his long-term stability.

He last worked at Keel Capital Management in Stamford but left to start a Queens-based company that creates environmentally friendly, green-building products. Before that, the spin-class-obsessed triathlete worked for a short time at both Pequot Capital Management and Grange Park, a hedge fund that’s now closed.

Key Facts About Brooks Perlin's Career Path

Timeline of the Couric-Perlin Connection

“If someone isn’t working out at three hedge funds, chances are it’s not just the workplace,” a source noted. “Brooks is a free spirit, but he’s a 33-year-old going on 18. And he hasn’t taken life seriously so far - he’s trying to figure himself out.”

According to the source, Perlin’s lack of focus stems from a “horrible accident that happened to an immediate family member” in his past. “It happened sometime before he was 10 years old, it was just an accident. After that, he was sheltered and he was very protected,” said our source, who adds Perlin “has a pattern of dating women much older and has a very complicated relationship with his mother over what happened.”

Meanwhile, we’ve learned that his mom, Anne Perlin, was busted last November for fourth-degree larceny. She was found guilty and fined $200 in a Stamford court, adding another layer of complexity to the narrative surrounding Couric’s partner.

Couric has often been spotted getting out of her limousine and heading to Perlin’s East Side apartment near Sutton Place, where a female resident complained that he “checks out every girl that walks by.” An ex-girlfriend of Perlin also backs up the claim, saying, “That’s totally accurate, he has a wandering eye.”