I started working with this woman 2 years ago and over the past year, we've built a really good friendship. We see each other pretty much daily and spend a lot of alone time together throughout the day. One day I asked her what she thought about the appropriateness of having sex with coworkers which led to us breaking the ice sexually. The next day I was feeling some guilt and a little fear that a FWB situation would not be wise. For one, she's married even though she's not happy and they both cheat on each other. It's more of a cohabitation thing. I was also worried that any feelings from either of us could affect our professional relationship. So I approached her and suggested that we not do that again for the reasons I mentioned above. She agreed and we have been work friends ever since.

The more I got to know her, the less I considered those problems as real problems and I became convinced that it could work with the right boundaries in place. I've made a move four times now to initiate something but each time she has rejected me. However, three times had stipulations around them that suggest she didn't really want to say no but had to or I regretted the way I made a move because I didn't take enough leadership. By the fourth time, I felt like she was leading me on. I brought her a flower and tried to talk to her about it again but she gave me yet another "not now but possibly later" type of rejection. I told her that I feel like she was leading me on and we had a fight but she finally gave me a solid no that she has no interest in a FWB relationship.

It's been a few months since then and everything has been normal. We are still friends who cut up and joke around constantly, we even flirt playfully from time to time, but nothing too suggestive. We'll take turns playing sexy songs while we work and it's been obvious that we are playing them for each other. Something tells me that she wants to, but she wants me to ask her in a certain way. If that's true, I feel like I know what she wants now and she doesn't want any words, just action. I can do that. But if it's not true, I embarrass myself again and this could make her second guess our friendship and her eagerness to come to work if I'm here.

Anyone else become victorious after multiple rejections or is it best practice to respect her first or even second rejection and move on? If it wasn't for the songs and the minor flirting, I would respect the rejections, but I can't tell if she's interested or just leading me on again. How have you handled similar situations like this?