A colleague of mine from work has asked me out a few times and while I like him, I'm not sure how good an idea it would be to date a co-worker. What would you advise?
First of all, you want to know how your company culture responds to this kind of thing -- there are some companies that strongly discourage relationships among employees and others that are more tolerant of it, so you need to get a handle on that. If you don't already have a sense of this, you could ask a more experienced colleague that you trust whether they knew of people at the company who have dated, and how the company (and other colleagues) responded. In particular, you want to know if there were any horror stories of workers whose reputations were tarnished or had to leave the company.
If your company doesn't frown on co-workers dating, then you have other considerations to think about. One is, how closely do the two of you work? If you're in close, everyday contact, it may be hard to avoid having aspects of your relationship spill over into your work together. Two is, how will your co-workers respond if they find out about your relationship? Some people are not bothered by it, while others may feel it could impact decisions about who gets to work on what and how resources are divided up, which may or may not be true. And you also have to think about how comfortable the two of you would be about being the subject of gossip and rumors at work.
So you really have to think about the implications of pursuing a relationship with your co-worker. And if you decide to pursue it, you'll need to define areas of discretion, such as where and how you can meet comfortably without involving your colleagues, and how you can communicate with each other without utilizing company resources like email and cell phones. And also, how to keep any disagreements or tensions in your personal relationship out of the office. To make it work, you really need to be confident that both of you can handle the range of situations that may come up.
As you can probably tell, I'm not a big fan of having relationships at work because the possibility for complications is so great. But the workplace is one of the places where you have access to like-minded, smart people, and so it's natural that it would come up. Generally speaking, my perception is that when colleagues maintain a quiet, private relationship that only becomes public when they deepen that commitment by getting engaged or married, companies usually don't mind. But when the relationship becomes public before then, especially between people who are working closely together, then it becomes an object of gossip and a real distraction that could wind up hurting your career prospects. Good luck.
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