I worked for the best boss in the world for 3 years, then left his department for another job at the university for more money and benefits. While working for him I considered him a cool person and friend, in addition to a great boss. He got divorced about 2 years ago and I and several other employees/coworkers took him out to dinner/drinks to show our support b/c he was having a rough time. He's truly a very great guy and I loved working for him. After I took the new job he and I had dinner a few times and talked about work, his dating life (was married for 20 years, has no game at all now), life in general and I consider him a real friend now.
But I get the distinct impression he wants to be more than friends, based on an email he sent me a while back that said something about how the woman he was currently dating wasn't as fun as me, and something he said last night at dinner. Even though he is not my boss anymore, nor in any sort of supervisory position related to my new job, I'll probably always think of him as my boss and have that line in my mind I won't cross with him. Last night we had dinner and drinks and again I got the impression he was trying to flirt. Despite my really good opinion of him he's got a lot of things I don't want in a potential date/BF: ugly divorce, bitter ex-wife, 3 kids, dependency issues, etc.
I really love this guy to pieces AS A FRIEND and am, for the time being, just ignoring his attempts to flirt in the hopes they'll stop. I dread that he will ask me point blank soon if we can be more than friend, and I am at a loss as to how to very gently let him down, but still be firm, and not have our friendship be strained. I think he could tell I was getting a bit anxious over how the tone of the evening was with the flirting b/c he commented I seemed tense.
How to do this with the least amount of rudeness or causing any hurt feelings? Suggestions appreciated.