Dear DD,

There’s this guy I realllllly like at work, we flirt hardcore so I really think he likes me too. We’ve hung out outside of work but only in group setting. I really want to pursue this further but I don’t know how to go about it or if I even should go for it.

Best,

Coworker Crush

 

Dear Coworker Crush,

Dating someone from work is…. Messy. To start off, if you happen to be reading the vibe wrong and pursue someone who isn’t interested then things at work will definitely get awkward with that rejection. The next obstacle is work’s policy about relationships. You may have to sign forms or it could be forbidden depending on the department or if one of you holds a superior position. Signing a document two weeks into a relationship would make just about anyone nervous. Or if work relationships are forbidden there’s added pressure on the relationship to know if it’s really worth losing your job over. Lastly, if your position titles are unbalanced any career achievements could be judged as ‘sleeping to the top’.

 

If I haven’t stressed you out enough yet then let’s skip right into the relationship. You’re starting a new relationship already spending the majority of the week with this person. So after spending the whole day together now you’re going to go have dinner or some other date plan. A relationship like this can definitely burn out quickly.

 

So say the relationship has burned out. Now you still see that person EVERYDAY at work. Maybe you’re both part of coworkers that all get lunch together every day, now what? Does the group split in half, are you left all by yourself, do you suffer through a group lunch with your ex every day? Dating a coworker is extremely complicated and there are a lot of obstacles to overcome. Of course, all relationships have their obstacles so a relationship with a coworker isn’t all that different.

 

So if you’re going to pursue this guy then the first thing I would work on is one on one time. Whether it be texting, lunch at work, or a light hearted hang out outside of work you want to build a special bond between the two of you. You can test the waters on how he may be feeling about you and express that you are interested in a relationship with him. Once you two have talked about those romantic feelings and are on the same page, you can progress in the dating stage.