I work for a small business and am very close with my co-workers. We often spend time together outside of work. I’ve spent the last few months subtly flirting with a co-worker who is 20 years my senior, but I’ve never attempted anything further as he is in the middle of a divorce, although I am very close with his children. About a month ago, I was at his house while his family was away, and we established that we are attracted to one another. We decided to proceed with a “friends with benefits” situation since our relationship is complicated. We hooked up but did not have sex. At the end of that week, he told me that he preferred the sexual tension and “the thrill of the chase” to our new arrangement, although he did not want to ruin our friendship. I was not interested in that as I felt rejected.
After a few days, I realized that I may have appeared too clingy and annoying—especially since a man in his 40s probably does not want his hookup texting him every day. I am never the clingy one, and it irritates me to think that I was. So I told him the following Monday that the chase was back on. Our flirtatious behavior has since become much more intense, while remaining discreet. It has now become almost a game in my head to have sex with him. I am not sure why. Should I make a move or bring this up with him? I would like to establish that relationship with him, but I am unsure if I ruined it by being too overbearing. Where do I go from here?