Reply #21: I would say [View All]

[sundog]

let him come to you.

From my closeted days, I know there is nothing more terrible than someone approaching you about something that you have not come to terms with.

There are good ways of dropping hints... you might even talk about the site & mention there is a strong gay community. Or if you have a gay friend irl, you might mention that. (Ex: "I went out with so & so the other day. He/she is gay.")

If you drop a few subtle hints, I think he will realize you'll be there when he takes that step.

You sound like a good bud. I appreciate the forethought. :)