Should I continue affair with him?

I had a short-lived affair with a colleague at work and ended it because I thought the idea of an office romance was dangerous for my career. I haven’t spoken to him since things ended a few months ago, but I am increasingly tempted to call or message him. He wanted us to continue because he said we could manage the office, but I refused. I regret that decision at times because we were very good together, even though it was just for a month or so. I want to see him again and talk about what can happen if we go down this path, but I am also nervous because I don’t want my feelings to cloud my judgement. How do I know if this is a good idea? What if it ruins things for me professionally?
You won’t know unless you have a conversation about what you both want from this. Your expectations may be completely at odds with his, and he may have the same fears you have. Office romances can be difficult if people in that relationship choose to let it affect their lives. It also leads to awkwardness if and when things don’t work out, which is why most people avoid them. Keeping your personal and professional lives separate has its advantages, but one can’t always control one’s feelings when it comes to another human being. I suggest you meet, talk it out, and consider what either of you can do to make this easier. You alone are in the best position to gauge any potential impact this decision may have on your future prospects at work.

Should I tell my boyfriend that some of his habits are extremely annoying, even if I know this will lead to problems between us?
If you want your relationship to grow, and assuming he wants the same thing, how can you not talk about the things that bother you? Without honesty, how will either of you evolve together?