How to Break the Ice
If you're in an unfamiliar social situation and you need to break the ice, try giving the person a sincere compliment to make them feel more comfortable. If you're new to the area, ask for advice on where to eat or fun things to do. You can also make conversation about the things that are going on around you, like mentioning a song that is playing or pointing out a new building going up across the street. If all else fails, try talking about pop culture, sports, or other subjects most people are familiar with.
Admit you're nervous. Going on a date isn't like meeting people in other situations...there are all sorts of things that tend to make you extra nervous! Admitting that you're nervous on a first date or even just around someone new can be a great icebreaker. They're probably nervous too, so just vocalizing what you're both thinking can really ease the tension. Notice and comment on something about them. Look at them, really look them over, and notice things about what they're wearing or how they're acting. Notice how they talk. Their accent. Look for if they're wearing something particularly nice, unique, or handmade-looking. Comment on these things that you notice. Ask them to ask you something. By letting them know that it's okay to talk to you and ask you questions, you can really help break the ice in your budding relationship. Say something like "If you have anything you want to ask me, go ahead." You can even give them more guidance. For example, "If you want to ask about my wooden leg, it's okay. I can talk about it." Be blunt. There's something to be said for just saying what you're thinking when it comes to the matters of the heart. If you see someone that you'd like to get to know better and then date, you can just tell them that. For some people it will be a turn off, but for most (especially the attractive ones) a break from all the games will be a nice breath of fresh air. Say something like, "I'm sorry, I saw you from across the room and I kind of felt like the air got punched out of my lungs. I just had to introduce myself or I'd never forgive myself." Comment on their name. If they have a somewhat unusual name (old fashioned, ethnic, anything other than the standard Sarah/John), then comment on and ask them about their name. You can ask if they were named after someone, how their parents chose the name, and if they like their name, etc. Ask them to settle a bet. The sneakiest and yet one of the most effective ways to break the ice with someone you don't know yet is to ask them to settle a bet for you. For example, say something like, "My buddy says this shirt makes me look like Bill Cosby during his blue period. What do you think?" or "All my friends say that guys won't go anywhere near girls with short hair. What do you think?" Do your research. Always, always, always do your research before going into any business meeting, whether it's with one person or three hundred. Read up on the company and as many of the key players that you'll be meeting as you can. Did your new partner previously work in a different industry? Did the company you're visiting just announce an upcoming reorganization? Look for things like this because you can comment on the information in order to start up a conversation. Ask them how they got into the industry. A good way to start a conversation with any individual you encounter through work is to ask them about how they got to the position they're in. Most people take a pretty wild route to get to where they are, so the conversation might even be really interesting! Ask about an award or honor that their company has recently received. This is the sort of thing you can find out about if you do your research beforehand. Just be sure that the award is fairly recent, so that they'll have more to talk about if they have not been with the company for too long. Hand out some Skittles. For ice breaking with larger groups, pass a bowl of Skittle or other colorful small candy around the room. Then, for each piece of candy that someone took, they need to answer a question about themselves. Color code the questions to the color of the candy. For example, a blue earns the question, "Where did you grow up?". A green can signal the question, "What is your favorite guilty pleasure tv show?" Brush up on your pop culture and sports. If you're not a pop culture or sports person, this can feel like a burden, but the fact is that pop culture is (by definition) pretty much the lowest common denominator. Do some quick reading of the Entertainment and sports sections of the paper/internet each day and you'll be prepared to have a conversation with far more people. Treat your employees, partners, and anyone else you meet with like an adult. Workplace ice breakers tend to revolve around games. Most of the time, there will be a few people who enjoy the games but most will just feel like you're treating them like they are in high school again (because similar games are so common in schools). You don't want to demean your employees or people that you're working with by making them feel this way. Try to find adult ways to break the ice. This usually means manning-up and starting a conversation yourself! Compliment them. A sincere compliment is always a good way to start things off with a new friend. Find something that you honestly appreciate or admire and let that show in your voice. Don't hold back! You can compliment something they work on, their personality, their sense of style, or anything else that you think of. Anatomy may not be the best choice! Be silly. Being a little silly can help someone who's uncomfortable loosen up a bit and see that you're nothing to be intimidated by. Take this approach if you know that people tend to see you as serious or scary. Do something like ordering your drink by saying, "Appletini. Light on the tiny," or reading them their horoscope in a silly voice after asking their sign. Be the new guy. Straight up admit that you're new or don't get out much and ask for advice on the area, fun things to do, or good places to eat. Asking people to talk about something they love is usually the fastest way to get them feeling comfortable an talkative. Respond to something going on around you. Pay attention to what's happening around you and you will easily find things to comment on. Changes in the architecture new buildings going up, someone doing something nice for a stranger, upcoming events, etc. All make good ways to break into a casual conversation with someone you're just meeting. Ask for a favor. This technique should be used sparingly, but it can be a good way to break into a conversation with someone. Ask them to do you a small favor (hold a drink, hold your place in line, grab something you can't reach, give you directions, etc). Just be sure that what you're asking of them only takes about 30 seconds of their time. When they're done helping, thank them and then break into a casual conversation. Ask what they're eating or drinking. If you want to break into a conversation with someone at a restaurant, coffee shop, or other area with food, ask them about the drink in their hands or the food that they're eating. Say something about how good it smells and then ask where they got it or what it is. You can then move into a discussion of food in the area or special ingredients in the item, etc. 
Admit you're nervous. Notice and comment on something about them. Ask them to ask you something. Be blunt. Comment on their name. Ask them to settle a bet. Do your research. Ask them how they got into the industry. Ask about an award or honor that their company has recently received. Hand out some Skittles. Brush up on your pop culture and sports. Treat your employees, partners, and anyone else you meet with like an adult. Compliment them. Be silly. Be the new guy. Respond to something going on around you. Ask for a favor. Ask what they're eating or drinking. 