So I wanted him to feel comfortable...he looked rather perplexed, intrigued and like a deer caught in headlights. So I made the first question easy.
Me: Did you enjoy staying the night in playing games?:
Old Man: YES (he held up the card)
Me: Ok now your turn
Old Man: Did you like the meal I prepared for you?
Me: Do you wonder why/ or does it bother you that I haven't invited you to my place yet?
Old Man: DEPENDS
Old Man: I'm not mad about it, I'm just curious as to what your place is like. I want to see what you are like at home, your personality so to speak...
Old Man: Does our difference in age bother you?
Me...(after a long pause, I hold up 3 cards): YES, NO, DEPENDS
Old Man: Why give me an example
(I go on to explain to him about the time I went with him to his friend's place on Election night, and how that lady was "fishing for info", and how I wondered what his friends thought of me, if they asked who I was, and how I was the youngest, (by at least 20 years) person there)
Old Man: Do you think about having sex with me?
Me: YES, but...I feel like sex could be a really good thing or a really bad thing. We've taken a long time to build a relationship, and I'm scared about what would happen if the sex is bad
Old Man: Wha...
Me: Because I know how I am, and I'm scared of the ramifications after we take it there
Me: You want to have sex with me don't you?
Old Man: (Grins): YES, DEPENDS
Me: Why depends
Old Man: Kind of what you touched on, on the ramifications that could happen afterwards
Me: Are you seeing/sleeping with other people?
Old Man: Have I slept with other people, yes
Me: REALLY (I didn't see that coming.....wow)
Old Man: It was awhile ago
Me: REALLY???? How long ago
Old Man: I don't know, a month or two
Me: Wow. I didn't expect that..... that's not that long ago( I really, didn't expect that, I was almost speechless)
We talk somemore about sex and how I didn't think he was having sex based on some things he has said, that I drew assumptions from.
We then go on, back and forth about our past, and what we want right now. Basically, he understands I'm not ready for anything serious, I understand he is seeing other people as well, and I told him, that if we ever did take it there, and decided to have a sexual relationship, then I would want it to be monogamous (although at this point I still can't see us having sex)....
...but there is one thing I didn't mention....he didn't ask me if I am/was seeing other people, and I'm on the don't ask, don't tell policy....guess he didn't want to know.....