Least sad (most cool) way to meet people/make friends/companions.

Depends on your situation and what you’re looking for. But mainly it depends on your interests.

Do you like sports of any kind that are televised? Going out to a bar (doesn’t have to be a sportsbar…probably better if it isn’t) to watch a game is a wonderful way to meet other guys with similar interests. (ie: the team you are watching.) And if it’s not a sports bar, there may actually be women there as well. Do this once a week (same day each week) and soon the bartender will come to know you. Then a couple regulars. Soon after, it can become your very own “Cheers”. (Different days may mean different bartenders.)

Do you do any activities? In these parts we have a disc golf course. Now, pretty much anybody can play disc golf, even if they can’t throw a frisbee. And there are often tournaments to join where you can meet the course regulars. It’s extremely laid back and fun, not to mention the mild exercise and the joy of being outside. Regular golf on a par 3 is another possibility; as a single you’ll be matched up with a group. Mostly hit or miss, but you never know.

You could join a bowling league, which is not nearly as lame as it sounds. Even if you suck at bowling, it doesn’t really matter, because you play against your handicap, not the other players. (A friend of mine scored with a hot chick who was in his bowling league. Rare, but I have the proof it has happened at least once.)

The bookstore suggestion is good, but it’s better for meeting dates than friends. (Not in any way a bad thing.)

As far as conversation material, movies are great. Music and books less so, but still an option. For conversations with other guys, sports is a tried and true fallback.

Good luck!