Speaking as a former manager and a current team lead: if one of my former staff were to approach me about this, I'd be really uncomfortable. There's a certain distance that leaders need to keep from their staff and this would cross that line in a big way. It seems to me that there are a lot of other candidates that wouldn't have potential professional repercussions. — baldPrussian 1 min ago

Can you clarify what kind of sexual relationship you're seeking with this woman? A one-off? Something more established? Also, it sounds like the two of you are comfortable discussing your own sex lives with each other. Is this true? — Dancrumb 2 mins ago

One of the best pieces of advice I ever got was this: "You cannot be responsible for others' feelings; you can only be responsible with them" — Dancrumb 51 secs ago

Seriously, you have discussed sexual things with her more than once, and she's responded by telling you sexual things, and now you're going over to dinner? What makes you think you need more help with this? It sounds like you are progressing towards your goal on your own. — Kate Gregory 50 secs ago

I'd note that this request is very different from the "Choosing Beggars" subreddit on Reddit. There, they try to get something for nothing; here, you're trying to establish a (reasonable) agreed-upon price and product. — baldPrussian 2 mins ago

I like what you said about "the effort you put into something tells people how important it is to you". One thing is not being able to do things, other is not paying attention when people is talking to you, agreeing to do things and then not do them. Sadly that shows his priorities. — Mykazuki 33 secs ago