Name: Should You Date a Coworker? Dating App Executive Answers | Fortune Office Hours
Uploaded: 2026-07-09
Duration: 4 min 30 s
Description: Office romance rules? Dress codes? Fear of an AI takeover? Match Group Chief People Officer D.V. Williams joins Fortune Office Hour to answer your real, unfiltered workplace dilemmas.

Office romance rules? Dress codes? Fear of an AI takeover? Match Group Chief People Officer D.V. Williams joins Fortune Office Hour to answer your real, unfiltered workplace dilemmas.

Should You Date a Coworker? Dating App Executive Answers | Fortune Office Hours

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Well, first off, how many cocktails were involved at this office party? That's where I'd start. Had to get that giggle out. Hi, my name is DB Williams. I'm the chief people officer at Match Group, and I'm here with Fortune Office Hours. At the office holiday party, I really hit it off with a colleague. We have started to have strong feelings for each other and have admitted to each other that we'd like to start dating. She is more senior than me, but not my direct manager. Should we tell our boss and what should we do if co-workers find out and gossip about our relationship? Well, first off, how many cocktails were involved at this office party? That's where I'd start. So the first thing you would want to do is talk to your local HR partner to understand what that company's uh philos. s op hy and policy is. And then based on that policy, that should help direct and guide you to who all needs to be notified. You know, relationships at work can be tricky. So I do think getting counsel from your HR partner is always great, even if it's not a hierarchical, uh, or reporting relationship. It's just good to know that you can openly date someone at the office and you don't have anything to worry about, especially not your job. Communication and transparency is key. It only gets messy when things are hidden or you haven't had the right conversations to understand that company's policy. Other than that, it should be fun. As it relates to office gossip, you shouldn't worry as much about that as long as you follow the proper channels for the company. As long as you're not bringing up issues or creating issues at the workplace by bringing your home drama and your relationship drama to work. Separation is key. We work in a business casual office, but some people show up in sweats. I'm a male manager with female employees. How do I navigate this with sensitivity? Well, first, it depends on what the issue is. If you have a business casual environment and sweats are not considered business casual, you should rely on what policy you have in place and have a conversation with all employees first to say, hey, here are the standards that are set by our organization and our policy. If you have a repeat offender, or someone who's coming to the office and not dressed what you would deem to be appropriate, having a transparent conversation and say, hey, this leans more toward casual, and our policy is more focused on business casual. If you choose to do it in a group and not single an individual out, they will be singled out if they're the only one to fit that category. And so you're not doing yourself any favors. But having a direct conversation with that person can build some trust because you did not put all of their business out in front of everyone. everyone else. When I worked in old-school manufacturing, you wore slacks and a button-down shirt every day, and on Fridays, you're allowed to wear polo. Now working in tech, it's a casual environment and it's to ensure that your version of casual and the company's version of casual match. As you've gone from casual Fridays or business casual Fridays to casual or business casual everyday. But we've definitely seen an evolution over time. I'm an executive assistant and I work at a large company that is implementing AI through many different layers of the company right now. As someone whose job consists predominantly of scheduling and building itineraries, booking travel, and creating pitch decks, I'm worried for my job security. What advice would you give me to futureproof my role and how should I be thinking about my next steps? I actually will look at this a little bit differently. Instead of futureproofing your role, you should be future-proofing yourself as a talent. And the way to do that is skill set acquisition. Get in front of the AI, learn as much as you can. Show them how the work that you're doing today can be improved with the technology, and I guarantee you there'll be more work for you to do. I don't believe that the EA role will be replaced by AI. I believe that some of the tasks, many of the tasks that EAs do today will become more efficient as a result of AI, but it will not replace the role of an EA. So my reaction to some of the issues Choosing these scenarios is very simple. They all exist. I don't believe that these scenarios, uh, will go away anytime soon because we will continue to evolve as organizations. New generations will come into the workforce, and they will have a different spin on ways of working, and we will need to continuously evolve with how we're working through those things. I've dealt with each of these in my job either today or in the past, and so they're very relevant to our workers.