6. Go for broke and ask if he has a new girlfriend.
“You can play it off as a joke, and if he answers, ‘No,’ then you’ve got a chance.”
You don’t have to beat around the bush to find out if he has a new girlfriend. If there are zero signs of any women in his life, then you can extend the subject into relationship talk and work in, “If you’re feeling lonely, how about going on a date with me?”