Im gonna say this and you can hate me for it...Im not bashing you but I am calling you out.

Your track record with dudes as friends lately isnt exactly stellar. Your gonna get drunk and fuck him because you feel bad for him , because he "says" your pretty and is charming in a mumbled drunk way...
If hes such a great guy he already has friends to lean on. He doesnt need a friend young enough to be his daughter.

You deserve better friends then that.

"Blessed are the flexible for they shall not get bent out of shape"
"You can discipline and Discourage or you can Discipline and Encourage"
"Gentle in what you do , But firm in how you do it"