Start with a handshake
A proper handshake conveys trust, respect, and equality. Make eye contact, smile, and shake from the elbow (shaking from the wrist comes across as limp). Touching hands signals our brains to release oxytocin, the feel-good hormone that promotes bonding and friendship.
First, look for singletons
People standing by themselves are the best option to approach, followed by groups of people who've left their circle open and welcoming. Two people standing shoulder-to-shoulder and groups of people that are closed off in a tight circle are likely not open to newcomers.
Practice on Your Server
If what you’re most nervous about is being ignored, test the waters by chatting up a waiter, waitress, barista, or bartender, suggests Kevin Kleitches. Your server's job is to make you feel paid attention to and happy, so there's a slim chance they'll snub you.
Offer your name, and repeat theirs
“Remember that a person’s name is to that person the sweetest and most important sound in any language,” Dale Carnegie wrote in his 1937 classic How to Win Friends and Influence People. The advice still rings true. Start a conversation with a strong and confident introduction, like “Hi, my name is Jane. What’s yours?” When the person responds, repeat their name back: “Nice to meet you, John.”
Acknowledge your acquaintances
If you've met someone before (even briefly) reintroduce yourself and say where the two of you met. To keep them from becoming flustered by not remembering your name upon seeing you, offer it in your opening line. Try something like, "Hi, I don't know if you remember, but my name's Jane. I think we met before at John's wedding." Follow up by asking for an update: "What have you been up to since then?" No matter whether they remember you or not, they'll be flattered you remembered them.
Consider what you have in common
After the name game, launch into something you and the person you're talking to can bond over. If you’re at a wedding, ask the obvious: how your new friend knows the bride and groom. At a networking event? Ask how they got involved with the hosting organization, or what other kinds of similar events they’ve attended recently. Don’t start with a complaint (ex: "These drinks are awful!"). You never know who they’re friends with, and you don’t want them to think you’re mean or hard to please.
Watch your body language
To look most at ease, lace your fingers together in front of you. Never cross your arms or fold them behind your back, which could make you seem standoffish. Lean in to show interest and to signal that you’re revealing something important about yourself.
Don't fire off too many questions
Give your new acquaintance enough information about yourself that they can comfortably ask their own questions. Don’t ramble, but don’t give short answers that don't make them have to scramble to ask more. “I'm just packing up for a trip to Europe with my two kids” tells them that you’re planning a trip and have two kids. Both are great details on which they could base follow-up questions. If it seems like your own questions are dominating the conversation, it might be time to find a new person to talk to.
Draw on their passions
Although you don't want to be the only one asking the questions, don't be afraid to ask follow-up questions like," Why?" or, "How'd you get started with that?" if you've hit on a subject the person seems passionate about. Encourage them to keep speaking by adding “hmm” and other filler words and phrases. “People love to talk about themselves, so be a great listener,” Cindy Cawley, an active fund-raiser and volunteer in Omaha, Nebraska, told Real Simple.
Throw out a hypothetical question
If you're in a group setting, such as a wedding table or circle of co-workers, ask a quirky hypothetical question for everyone to discuss. Mention something you heard on the radio, or bring up an event that just happened and ask what everyone would do in that situation. Keep your subject appropriate, but don't be afraid to make it light and fun.