When it's kosher to canoodle with a colleague
A viral moment in Central Park may have just become one of the most expensive personal decisions in Big Law history.
Nathaniel Cullerton, a partner at elite New York law firm Wachtell, Lipton, Rosen & Katz, was reportedly placed on leave after a video surfaced showing him kissing a junior associate in Central Park. The timing couldn't have been worse.
According to multiple reports, Cullerton was set to join Gibson Dunn as part of a high-profile lateral move led by renowned trial lawyer Bill Savitt. Following the video's release, that opportunity reportedly disappeared—potentially costing Cullerton tens of millions of dollars in future compensation.
Beyond the personal headlines, the story highlights how quickly reputational issues can become business issues in today's legal industry. It also raises questions about workplace relationships, power dynamics between partners and associates, and the impact social media can have on even the most successful legal careers.
Whether the ultimate consequences are justified or not, one thing is clear: in an era where nearly everyone has a camera, private moments can have very public—and very expensive—consequences.
Office romances are making a comeback. Not because people suddenly believe in dating colleagues but because they're running out of places to meet people.
Think about it.
Most adults spend 8–10 hours a day at work.
They've stopped going to community events.
Their friends are either married or exhausted.
Dating apps feel like an endless cycle of interviews, ghosting, and decision fatigue.
So the office quietly becomes the last place where relationships can grow the old-fashioned way.
You see someone repeatedly, you watch how they handle pressure, how they treat the intern, whether they take accountability when things go wrong or if they're kind only when it benefits them.
That's far more useful than a perfectly curated dating profile.
But office romance comes with a catch.
The same familiarity that builds attraction also blurs boundaries.
A breakup doesn't just end a relationship. It follows you into meetings, team lunches, performance reviews, and Monday mornings.
I've noticed something interesting as a matchmaker.
People say they would never date a colleague.
Then they describe the kind of partner they want:
Someone they've known for a while.
Someone whose character they've observed.
Someone they naturally became friends with.
Ironically, they're describing a colleague.
The question isn't whether office romance is good or bad. It's whether two emotionally mature adults can separate their relationship from their professionalism.
Because the problem is rarely where you meet. It's how you behave afterward.
Would you date someone from your workplace, or is that one boundary you'd never cross?