Hi, I happen to be in a position where there's a good bunch of women my age, at work and several social groups, I talk with on a regular basis - many of whom seem like they could be interested in me. I would definitely take the risk and escalate with some, if I had any clear indication that they're on the market. Now the only insert I've used in casual conversation for this purpose (and worked wonderfully) is - "How do you spend your weekends?". Another one I thought might work is - "Tell me about the important people in your life". However, I wonder if anyone here has a better idea to extract a woman's status covertly from mundane parley without exposing my intent.