Turn Fear into Fun: How to Start Conversations with Strangers

Talk to Strangers Forrest Gump

You are going on an excursion today and the bus that gets you there will take an hour. After waiting in line you hop on the bus, search for seat 35B, place your bag underneath the seat and settle in. It seems like everyone is on the bus by now and you will be taking off in a minute. The seat next to you is empty, thank goodness, now you can put your feet up and sleep. All of a sudden someone runs onto the bus last minute and plops down next to you. He’s cute and the book he just pulled out is the one that you have been meaning to read since you got here. Do you put your headphones in and sleep like you had planned or ask him about the book?

Last week we talked about a few non-awkward places you can meet people while traveling. This week we are going to trod into the uncomfortable; striking up a conversation with a stranger. There are strangers around us all the time, it’s just that at home we usually have our friends with us so we don’t have to step out of our comfort zone and speak to that girl with the wicked outfit next to us in order to feel connected. When you are traveling alone however, you find yourself surrounded by strangers all the time without a recognizable face in sight. So what do you do? I say you ignore your mom’s advice and talk to any stranger you are drawn to or find interesting.

Being totally at ease striking up a conversation with a new person will help you tremendously in both your personal and professional life and it’s empowering. Chatting the right person up can provide you with many opportunities you wouldn’t otherwise have found, and it’s fun, but you won’t know until you try. I know that it can be scary; your fear can block opportunities and may feel overwhelming. So what is it that’s scaring you? Is it fear of saying the wrong thing? What is the wrong thing? More than the actual words exchanged, people remember feelings. When speaking to someone, you want to focus on how you come across more than what you are saying. So if you give off an air of confidence and comfort that is what your new friend will pick up. Here are a few things you can do to create that air.


Talk to Strangers Friends Conversation

Smiling is the most basic biological human expression. It is universally recognized, which means that it has the same meaning wherever you are in the world. Research shows that smiles are even contagious! When someone is smiling at us it’s difficult not to smile back. Plus, smiling helps to reduce stress. So if you are nervous about walking over to begin that conversation take a deep breath and smile big, it will help get you ready to take the plunge and activate your brain’s reward mechanisms to release a chemical that makes you happy. If that’s not enough, smiling actually makes you more attractive in the eyes of the person viewing you. So if you are about to walk up to a crush, that smile will help set the mood :). The only catch is that the smile has to be genuine, so get those pearly whites out and smile ear to ear. Remember, you are about to make a new friend!

Remember that having a conversation is a mutual experience

So you’ve got your most beautiful smile out and you are walking up to your new friend. As I mentioned above, most of our fear around talking to strangers has to do with the anxiety we experience when thinking about if we will say the right thing. Conversation, however, is a mutual experience and both parties need to benefit from it. So instead of approaching someone thinking about if you will be interesting enough or say the right thing, think about how you will both benefit. You want to be entertained as well and get something out of the interaction, so be yourself. If you spend too much time catering the conversation to the other individuals’ interests, will you be bored? Make it fun, keep it light and don’t take the conversation personally.

Don't take it personally

If a conversation isn’t going well don’t be offended or upset. Maybe they are having a bad day, maybe you weren’t meant to be friends, maybe you should change the subject, or maybe you are both shy and not the best at sparking up a conversation. You can say that you have to get a new drink and walk away orrrr you can give it one more go. I believe in transparency and honesty, so if a conversation isn’t going well just admit it. You can even make a joke of it by saying something like “We’re working really hard here, eh?” or “I’m sure we have interests in common, but we’re having some difficulties finding them. How about you tell me what you love talking about most.” Being honest about the awkwardness can relieve the stress on both ends of the conversation and if nothing it can provide a laugh. We all remember our first time, mine definitely was not smooth sailing, but you talk it through and figure it out. It gets better every time.

Show interest

Talk to Strangers friends conversation

If you’ve made it through the awkwardness, and I know you will because I believe in you, then you’ve jumped into a conversation. Now make sure that it’s a good one by showing interest in what the other person is saying. If they tell you a joke, even if it’s not super funny, you should laugh (maybe even really hard to make them feel special). Remember that having a conversation is a mutual experience and they might be just as nervous as you are. It’s not satisfying to have your comment go ignored, so don’t do it to your conversation partner either. As humans we all enjoy attention. If you can provide that attention and make the other person feel as though they are interesting, you have already made the conversation that much easier for both of you because the other person will become comfortable around you. These days kindness is so rare that it can be a surprise, so show them kindness and you will stick out as a great conversation partner.


People love talking about themselves, so let them. If you ask a question that seems to light someone up make sure to notice and ask follow up questions. Don’t just change the subject or run through the list of questions you had created in your head. This will not only keep the conversation going, but it will allow you to get to know them better. Just make sure that the questions you ask are open-ended so that you will get more than a yes or no response.

Ask open-ended questions

Open-ended questions are ones that can’t be answered with one word; they require a bit more explanation. So don’t ask “How’s it going?” ask “What’s the best thing that happened to you today?”. Now that you have them responding with more than just good, you might find a point of commonality in what they say to go on or have something that you can ask more about. I’m sure you have all experienced the dreaded “Hey, how are you?”, “Good, you?” conversations that get awkward really quickly, so try something else. Albert Einstein is famously quoted as saying that the definition of insanity is doing the same thing over and over and expecting a different result. You’re not insane, maybe a little weird like me, but not insane. I might be a bit biased, but I think that’s a good thing. Use your weirdness to make the conversation more fun.

Use humour

I could have a conversation with a wall and be howling the whole time. We all think we’re funny and we are. So keep that in mind while having a conversation with your new friend. The number one quality we all list as a must have in a person is a sense of humour. Try out a few of your corny jokes and see which one sticks. Making the conversation light and funny will encourage them to do the same. Remember when I said that people remember how you made them feel more than the actual words you said. If you can make them laugh, they’ll remember that you’re funny and a good time. You don’t have to prepare like you’re about to do standup, just let it come naturally and keep it relevant.

Don’t rely on alcohol

friends conversation drinks

I know that a drink may seem like the best way to manage some of the anxiety you’re feeling right before you walk over to a new person, but keep in mind that it also brings out another side of you. I’m not apposed to a drink or a fun evening; I’ve been out a time or two. Just think about if you ever want to see this person again or if you want to build a connection with them. If so, then alcohol might not be the way to go because, that’s not really who you are on a day-to-day basis. Of course, there are times when you are at a party and alcohol is involved, just gauge the situation. Don’t be Bob who is a riot when he’s drunk and an introverted shy guy when he’s sober, because all those who met drunken Bob will be expecting that every time they see you now, and then you’ve got a problem. Just be you, because you’re awesome and you want your new friends to think so too.

Get in a conversation mindset

I like to dance and sing out loud before I head out to a social occasion, it gets me in the connection zone. Figure out what gets you ready to interact with other people and do that before you head into a social situation or are about to walk up to a stranger and start a conversation. Maybe it’s just a few deep breaths, that big smile and picking something out about them to initiate the conversation. Do what works for you and remember to have fun, connection is a mutual experience so make sure you get something out of it as well. Maybe that’s your ritual, you decide what you want out of the conversation first and then you go over and get it. Jonathan Goldsmith says: “So many of us let others determine what we are worth. It’s our duty to make that determination ourselves.” I agree and I think you are worth a whole lot, so in the words of my girl Hilary Duff “don’t let the fear of striking out keep you from playing the game.”

My Challenge to You

I covered a lot and I know most things are easier said than done. I also know that the best way to get good at something is to practice. So I have a challenge for you if you’re up for it. Try striking up a conversation with a stranger today on your way home from work or while you are at the grocery store. Practice while you are still at home and it will be easier while you are traveling. You might just make a few new friends.

As my gift to you, here are a few ideas you can use as inspiration to help you strike up that initial conversation:

If you are just getting your feet wet and aren’t ready for this, check out our post on 7 non-awkward places to meet new people while traveling. You can also always reach out to me; I love new friends and will be easy practice.

How did these lines or any of the advice above help you strike up a conversation? Is there anything else that you would suggest to help make the process of striking up a conversation with a stranger less intimidating?