Any intimacy at all yet? If not I would definitely start with a couple of drinks to relax and lose the inhibition....word to the wise, couple drinks means like 2 glasses of wine, couple beers, NOT five shots of Jack!! You don't want to be a sloppy mess. If he has also been single for many years he probably also wants to get to snogging! After five years though, I imagine neither of your confidence levels are at a prime right now. Feeling good is an important first step!!!!!
My advice:
1. Compliment him! Stupid little stuff....his shoes are cool, you like his haircut, he's got good taste in music...ya know, little things. Those little compliments will weigh on a guys head all day (with a big ol' smile attached to the front of the head ;) When he knows you're just as into him as he is into you, everything will flow more naturally.
2. Touch him! Even if you're out in public you can do little things like lightly rub your fingers up and down his back for a minute or two (like a little mini massage). If you're hanging out at home tell him to sit on the floor in front of the couch and give him a shoulder massage. These things are not TOO personal as a first move but will help break the "personal space" boundaries. Plus, him getting comfortable your touch and wanting more of it is always a good thing.
3. Don't have a "big talk" about it! You know, the "do you think we're at the point of snogging yet?" talk. Put's a little too much pressure on the situation. It will make for a VERY uncomfortable first snog.
4. If you have already done the making out, touching, almost snogging, etc., I think the only other advice is next time you're in one of those great long kisses, just grab it! You'll both be glad you did!
Hope this helps!
Good Luck!