Questions To Ask Before Dating Someone You Work With

The safest option is to avoid getting romantically involved with a colleague, but not everyone wants to stick to the rules because where’s the fun in that, right? If you’re really interested in this guy you work with then you should go for it. However, there are a few questions that you need to consider asking him before you go there to make sure you know where you stand.

  1. Do you want to go on a date? This is the only way to determine whether or not there’s real chemistry here. Maybe you like the idea of dating him more than you would like the reality of it. Being outside of the workplace in a different environment might help you to figure that out.
  2. What are you looking for? This is the most important question that you must ask before you go any further. If you’re looking for something long-term but they’re all about keeping it casual, then you know for a fact that it won’t work out. That’s not something you should take a chance on. You only need a simple answer to this question and it will make you realize if he’s worth it or not. If you’re not on the same page, it’s not worth the trouble.
  3. Do you want anyone to know? You need to make sure that you’re both on the same page before you start dating. Some people don’t like anyone to know who they are dating, especially in the workplace. It can make things really awkward if you don’t make your feelings clear. Do you want to tell your boss and your other colleagues or would you prefer that it stays between the two of you? Remember that no one really needs to know as it’s your personal business. You just need to make sure you both have a clear understanding.
  4. How do you feel about me? Although it can be a hard question to ask, in this situation it might be necessary. If he doesn’t like you as much as you think he does, then it might not be worth the trouble. Dating a colleague can be really awkward if you break up, and if it looks like it’s not going to last then it’s probably not worth starting anything.
  5. Are we allowed to date in the workplace? Some workplaces don’t approve of employees dating each other and they could have a policy that prevents you from doing so. Before you do anything, you need an answer to this question. Make sure you do your research and talk to your boss if you need to clarify anything. There’s no reason why you should risk getting fired.
  6. Do you have any exes in the workplace? This isn’t a make or break it question, but it is helpful to know if there could be any jealousy at work. It can be hard enough trying to keep things a secret, but if there’s an ex who still has feelings for your new guy, it could make things really uncomfortable for you. If that’s the case, you need to weigh up the pros and cons and decide if it’s worth it.
  7. Will this change our working relationship? The last thing you need is your relationship to become a distraction that affects the way you perform at work. You don’t want to be in a position where you could get fired because your performance is lacking. This could happen if your male colleague starts texting you from across the room or acting in a way that he wouldn’t usually act. It might seem flirty and exciting in the beginning, but if it messes with your career, that’s a no-go.
  8. Are you emotionally mature enough to handle this? This shouldn’t be a hard thing to ask if he’s a decent enough guy who wants to treat you right. You can tell if he’s mature if he can answer the question or not. If he laughs or doesn’t give you an answer, then chances are, he’s not going to handle it well. Dating a colleague can be fun, but it can also be awkward if things go wrong. There’s also the chance that he could get clingy or over-attached and that can be a huge problem in the workplace. You need to decide if this guy is really worth it or not.
  9. What happens if we break up? If it’s a mutual breakup with no bad feelings, then nothing really has to change. But if the breakup isn’t mutual or things go badly wrong between you two then it might make things really uncomfortable at work. Can you put things aside and work normally together? That might not be as easy as you think. You need to work out if one of you is willing to change departments or change roles if needed. And if you’re not willing to sacrifice your job then you probably shouldn’t take the risk.
Coralle is a freelance writer with an interest in relationships, women's health and parenting. In her free time, she enjoys reading, watching new Netflix shows and spending time with family.