Some tidbits:
Be prompt, generous, and sincere in your compliments. Ideally, don't use plain adjectives - use descriptions. (Exceptions here are compliments on articles of clothing - "your boots are AWESOME!" is kosher.) It only feels silly from your end. If you are just trying to make friends, avoid anything that (given your and the potential friend's genders) would appear laced with sexual interest, unless you can pull it off with genuine innocence and then reliably follow up with genuine innocence instead of changing tacks midway.
Have a "standby" interaction prompt that you can pull out in lulls which isn't threatening, is generally well received, and provides a hook for further conversation. I usually offer people food. I'm sure there are others that would do - if you're trying to conduct an informal survey of something, for instance ("Hey, I'm trying to find out different ways people celebrate St. Patrick's Day, what do you do?), that would probably work too.
Learn to pick apart people's dialogue for followup questions - you can practice this on fictional dialogue; just take a good-sized sentence and write down five followup tangents. Example:
"I went out to Cape Cod last week with my friend Tess and we found some sea glass."
Followups:
"Ooh, do you go to Cape Cod a lot?"
"Neat, what else did you do there?"
"Wow! How long did you stay on the cape?"
"Cool - what are you going to do with the sea glass?"
"Hm, I don't think I know Tess - tell me about her?"
Note that these all prompt the potential friend to talk, rather than providing an excuse for you to do so (any of the above would be preferable to, for instance, "Hey, I went to Cape Cod once and had the most fantastic lobster...") Also note that each sentence started with a particle that shows interest. Eliminating these runs a significant risk of making it sound like you're just interrogating the person. And: it is quite important that you actually want to know the answer to the question you pick. If you can come up with lists of five but don't give a crap about how any of them would be answered, you're talking to supernaturally boring people, you're a misanthrope, or you're doing the exercise wrong.
Go ahead and be the first to suggest exchanging contact information. On the internet, this means e-mail or better, IM. In person this means a place to meet next, or possibly phone numbers or addresses (or e-mail or IM). It's scary to most everybody else, too, so don't expect them to do it. Leave a line of social retreat if they never want to hear from you again, avoid any requests for contact info customarily laced with sexual tension, but do make it clear that you think they're neat and you'd like to be their friend. You can even haul out the elementary school line "Wanna be friends?" - if it makes you feel more comfortable with it, go on a brief tangent about how "we lose so much when we leave elementary school and it's no longer socially acceptable to make friends by walking up to someone on the playground and asking if they want to be..." beat... "Wanna be my friend?".
Cultivate social spontaneity. This one is hard to define, so I'll give an example. I was waiting for a bus and a woman I'd never met before in an awesome homemade knitted cloak tottering along on crutches said she loved my jacket. (It was my florally embroidered denim thing, by far the loudest thing I own). I was trying to make friends, so instead of thanking her and looking away, I fired back with a compliment on her cloak and soon had her talking up a storm about knitting. When she was interested in what I did with my spare time, I didn't talk about school, even though that was most salient to me at the time - I talked about cooking, gambling that the domestic handicrafts have some overlap in their aficionados. I told her I planned to make pumpkin bread as soon as I had a can of pumpkin. Which it just so happened to turn out that she had in her cupboard, and she lived in my apartment complex. So I went home with her, accepted the can of pumpkin, went home and made bread, and brought one of the loaves over to her place, where I hung out for another couple of hours chatting about textiles, her Hassidic Judaism, and her multiple personalities. (I am no longer friends with her over differences of opinion on a political/ethical matter, but it's still a great making-friends story.) Social spontaneity is what let me go to a stranger's place for canned pumpkin and bring her a loaf of bread later.
Excellent comment!
If you can come up with lists of five but don't give a crap about how any of them would be answered, you're talking to supernaturally boring people, you're a misanthrope, or you're doing the exercise wrong.
Wow, this sounds really familiar to me, which probably implies that I'm a misanthrope. Do you have any remedies? To me, most people just seem to be pretty boring and I want to change that ( don't like to be a cynical asshole), but every time I start a conversation with a random student from my university I start to feel even more ...
This is a supplement to the luminosity sequence. In this comment, I mentioned that I have raised my happiness set point (among other things), and this declaration was met with some interest. Some of the details are lost to memory, but below, I reconstruct for your analysis what I can of the process. It contains lots of gooey self-disclosure; skip if that's not your thing.
In summary: I decided that I had to and wanted to become happier; I re-labeled my moods and approached their management accordingly; and I consistently treated my mood maintenance and its support behaviors (including discovering new techniques) as immensely important. The steps in more detail:
1. I came to understand the necessity of becoming happier. Being unhappy was not just unpleasant. It was dangerous: I had a history of suicidal ideation. This hadn't resulted in actual attempts at killing myself, largely because I attached hopes for improvement to concrete external milestones (various academic progressions) and therefore imagined myself a magical healing when I got the next diploma (the next one, the next one.) Once I noticed I was doing that, it was unsustainable. If I wanted to live, I had to find a safe emotional place on which to stand. It had to be my top priority. This required several sub-projects:
2. I re-labeled my moods, so that identifying them in the moment prompted the right actions. When a given point on the unhappy-happy spectrum - let's call it "2" on a scale of 1 to 10 - was labeled "normal" or "set point", then when I was feeling "2", I didn't assume that meant anything; that was the default state. That left me feeling "2" a lot of the time, and when things went wrong, I dipped lower, and I waited for things outside of myself to go right before I went higher. The problem was that "2" was not a good place to be spending most of my time.
3. I treated my own mood as manageable. Thinking of it as a thing that attacked me with no rhyme or reason - treating a bout of depression like a cold - didn't just cost me the opportunity to fight it, but also made the entire situation seem more out-of-control and hopeless. I was wary of learned helplessness; I decided that it would be best to interpret my historically static set point as an indication that I hadn't hit on the right techniques yet, not as an indication that it was inviolable and everlasting. Additionally, the fact that I didn't know how to fix it yet meant that if it was going to be my top priority, I had to treat the value of information as very high; it was worth experimenting, and I didn't have to wait for surety before I gave something a shot.