My Fault

I am super confused right now. I have a male friend. We worked together in the past from 1997-2004. I have adored him for years (in a purely platonic way). We have stayed friends since. We regularly correspond and meet for lunch about once a month.

Last time we went out to lunch, he made some suggestive comments about how good I was looking and that we should ditch lunch and head to a hotel. I laughed it off. He often expresses sexual frustration in his marriage. As a friend, I let him vent and I have no problem with listening to him talk. (Keep in mind, he was a good friend to me when I got divorced and subsequently went on a dating/sex bender of epic proportion and I did share with him limited details of my escapades)

Recently there was a negative turn of events at the company he works for and he's seeking new employment. I suggested he talk to my boss about coming to work here. They have met several times now and are at the point where they are negotiating an offer. So his coming to work here is looking promising.

Last week, I got a text from him. He asked me about the cell phone plan here at our office and I replied and then he said:
"Hope we will be together soon. Any dating going on with you?"

Me: I have dipped my toe back in the dating waters...I'll fill you in later.

Him: Ok, always like the sexy details things are slow here so I like hearing things. Gives me things to think about for later. very lonely. text me details"

Me: It's not those kind of details...there has been none of that and will not be anytime soon.

Him: Well maybe we need to fix that for both of us. not sure how to make it happen. I know it is awkward but it is always on my mind.

Me: I don't need fixing, I'm all set.

Him: [Wife] is working...what to do all alone?

Me: How's her new job going?

Him: Sorry but really horny, sorry to embarass you but need something

Me: I totally understand. I'm not embarassed, I just love our friendship too much to go there.

Him: I hear you but I definitely think about it. About you.

OK, so....you see what I do there? I dance around and at the end, I am taking care of his feelings despite the fact that in my living room I'm screaming at my phone "Nooooooo!!!! Don't do this!!! Don't say this shit to me!!! Don't put me in this position!!"

So now I'm at the point where I could still go to my boss and tell him not to make this deal happen and I'm totally on the fence. The thing is I am accustomed to men talking to me in disrespectful ways and I'm not sure it appalls me anywhere near as much as it should. I am empathizing with him, I am taking care of his feelings. And I'm excusing the behavior and quite honestly, I have ZERO idea how I really feel about it.

I think if he worked here it would be fine. But I'm not sure. And I just want to give him the benefit of the doubt that he will behave himself and that was a momentary lapse in judgment sending me those texts. But he was suggestive at our lunch and he has been flirtatious in our correspondence since then. I think if I put him firmly in his place with this topic that he would respect me and so naturally, I am 5 years old again and I think this is my fault....I'm not speaking up, I'm not saying no. I'm leading him on by not being definitive with my words and by being all understanding. So if he puts his hands on me, it will be my fault.

I worry that if I say what I need to say, he will not be my friend anymore and I know....I get that #1 I don't need friends like that and #2 if he were to get mad at me for that then he was not being a real friend and all that. But then I worry about causing problems at work if he does come to work here. I can't end up unhappy in this job that I've come to really love. And so, I don't know what to do. Or how to do what I know I need to do.