I have this old friend/coworker with whom there has always been MASSSIVE sexual tension and underhanded flirting. She has recently become single and was pretty down in the dumps over it, and I was there to console her heavily (not that I was trying to do that just to get at her - I actually did want to make her feel better and help console her, she had done the same for me). But now I can't stop thinking about the idea of trying to flirt with her, but now I am overthinking things and losing game. She just got her wisdom teeth taken out, and we threw around the idea of meeting up sometime soon. My question: should I continue trying to talk to her regularly and risk coming off as pushy, or should I lay off for a day or two and see if I can get her to hang out this weekend (and hypothetically lay some groundwork or something)?