How do you make friends out of strangers?

It takes me a while too to really make a friend. I am more of the 'few friends, but once you're a good friend, it's a strong, long-term friendship' thing'. That doesn't mean I have more causal friends, but similar to you, it's hard for me to strike up a conversation with someone out of the blue. Age, interests, among other things can make things difficult.

Keep in mind that 'forced' conversations make it hard to make friends, especially if you (let alone all involved in the conversation) aren't very outgoing.

Generally, I found a few ways to make things better:
1.) Going to a group discussion thing with another friend helps. That allows you to have someone you already know, but also allows you to get to meet new people. Keep in mind that while it is a good idea to bring someone a bit more outgoing than you, be careful that you don't have that person talk FOR you.

2.) Playing games like Phase 10, Skip-Bo, etc really is a nice ice breaker. It takes the awkward feeling away as you focus on the game.

3.) Same with video games. NOT ONLINE GAMES, but video games you can get together with people to play. And just in general, same with common interest meetings....

Jam it back in, in the dark.