Why would someone that's supposed to be a friend..

I'll say a couple things - first of all, if you're not ready, you're not ready. And if all you see him as is a friend, then that's all you see him as. You're under no obligation to pretend otherwise, so if he continues expressing interest, just be honest and upfront, like you have been already. If he still won't cut it out, you can also ask for some time to yourself (i.e., not being in contact with him).

You do mention, though, that situations like this "got you into a lot of trouble in the first place" - so it seems like there's a history here that may be influencing how you feel about his comments. From what you've written, even though it seems like he may have a few issues with boundaries and social appropriateness (I wouldn't ask a friend if they were into me while they were consoling someone going through a custody battle, but hey, maybe that's just me), he's not necessarily saying or doing anything inherently wrong. Provided he doesn't ramp up the attempts into the creepy zone, try not to sweat it too much - because, again, you have control over what happens here.

 

It sounds like, he feels very alone, then suddenly, his friend is gay. Suddenly, someone your close to has one more thing in common. I dont think he means to make you feel like that. I think he is just looking for companionship more than sex, but being a man he doesnt quite know how to say it. You could explain to him you are there for him, and that he can have your companionship, but no more, as your not ready and really it just sounds like he needs a shoulder to cry on.

 

"Then today he's already (3rd day out) asking if the friend I was texting a bit while hanging out - if wed done stuff sexually."

So on your 3rd day out hes already asking if you've done stuff sexually with another friend? He sounds extremely clingy and jealous. It sounds to me like hes thought about you sexually for a long time and he has feelings for you way beyond a friend and the prospect you could be sleeping with another man has made him extremely jealous and upset. I would keep your distance. Don't let him manipulate you into thinking he has lost those feelings of wanting more then just a friend because I can assure you he while may say he understands he would jump at the opportunity right now to be more then just friends. You should take a break from the friendship and not have any contact with him to let him get over his feelings.
You are 100% correct about one thing, sleeping with friends is an absolute relationship killer. I slept with a somebody I had gone on one date with and then we decided to becomes just "friends" and ended up sleeping with each other and holding hands everywhere and cuddling all the time like we were in a relationship and it went on for 2 months and I fell in love with him. I thought it would turn into something more, but in the end I found out he really was just using me and the care he had for me was fairly minimal as a friend. It broke my heart. Never sleep with a friend, or get into a FWB situation if you are the emotional type that might get attached. FWB's 9/10 never turn into anything more and almost without exception somebody will get hurt. Just got out of this relationship about a month ago so it's very fresh in my mind. It was an absolute nightmare.

 

Good luck with it all!!!

 

That's cool I live pretty close to there!