Last week, I went to see a burlesque show for the first time. I didn’t realize that it was basically a strip tease dance performance. The thing that really struck me was the fact that these women were far from skinny. I don’t even feel comfortable walking around the beach in a bikini and there these women were doing tassel twirls from their tits while flaunting their muffin tops and cellulite without any shame. I immediately wanted to interview these women for one of the websites I write for covering the live entertainment scene because of the positive messages of body image these women were displaying through their risque performances.
After the show, the new friends I had made at the hostel I was staying at in Portland offered to stick around so I could go talk to them, but I was too shy. I didn’t want to interrupt the conversation someone else had started with them. I didn’t want to be rude, I didn’t know how to open, and I basically choked. How do you start a conversation with someone without it feeling like an interview or some kind of interrogation?
While waiting to talk to one of the performers in the middle of a conversation with a couple of the other audience members, I saw another one of the performers talking to someone in my group. It felt less intimidating to jump into that conversation since I knew my new friends wouldn’t think I was being rude. When it came down to it, my friends helped me get the conversation started and I kept it going by asking follow-up questions. But what happens when your friends aren’t there to set you up?

The reality of starting conversations with perfect strangers is that at some point, you’re going to have to learn how to do it all by yourself. As a former sorority girl, I’d like to think that I was highly trained at having conversations with just about anyone after spending hours perfecting the art of a well-executed bumping pattern every year for sorority recruitment. Here are a few conversation starter tips I’ve picked up since my sorority days that have worked well for me during my time in Portland where I don’t know a soul.
Smile and say a hello.
This is by far one of the easiest ways to start a conversation with someone. No words need be exchanged when a smile says it all. Throw in a simple hello and that’s all you really need to start a conversation with just about anyone. While staying at my first hostel for almost a week, I’d hang out in the common room areas and smile to anyone who sat down next to me or made eye contact with me. When someone smiled back, I took that as an invitation to start a conversation, and would ask that person what brought him or her to Portland. Whenever someone new made their way into the women’s dorm, I’d smile, say hello and introduce myself which led to conversations about reasons for visiting Portland. My first day at the dorm, I did this to the first four women that entered the room and then asked if they were hungry. One by one, I invited each of these women to have lunch with me at this food truck haven known as Cartlandia. They all said yes and the conversations kept going from there.
Request a small favor.
Do you have the time? Do you have change for a dollar? Do you know when the bus is supposed to arrive? Can you watch my laptop while I use the bathroom? These are all very simple requests that can easily get a conversation started with anyone open to one. In mundane situations like waiting for the bus or working out of a coffee shop, a simple request can break up the monotony of someone’s everyday life with a touch of human connection, even for a brief moment in time. The other day, I installed a new email capturing plugin on my website, but I wasn’t sure if I installed it correctly, so I asked the person next to me if they could do me a favor. He seemed reluctant at first, but then I told him what I was trying to do and it led to a conversation about things I write about and he ended up helping me verify that my plugin was not configured properly.
Pay someone a compliment.
Another easy way to start a conversation with someone is through a friendly compliment. I can’t tell you how many times people have started conversations with me by telling me they liked my purse, my shoes or my necklace. I’ve certainly done this one myself, especially whenever I see a man rocking a hot pink tie. The other day, one of the women in my dorm room at the hostel was a retired meteorologist whom I later learned was a marathon runner. I couldn’t help but notice how nice and toned her legs were for her age so I paid her a compliment and told her so. I figured she would appreciate the compliment, especially at her age, and she most certainly did. People appreciate compliments and are more willing to talk to you when the compliment comes across as sincere and genuine.
Ask for an opinion.
This is probably one of my favorite ways to start a conversation with someone. It’s a classic technique used by pickup artists, but it’s also ideal for writers and journalists working on a story that could use the added insights of an alternative perspective. Asking people questions is a sure-fire way to get a conversation started, especially when that question is an engaging one. For example, I’m working on a piece about the best coffee shops in Portland so I could open a conversation by asking someone if they knew of any good coffee shops in town and which ones he or she thought were the best. Another example is asking someone if they think a joke is funny or lame. In fact, when I was younger, that was exactly how I made friends. I’d learn a new joke every morning and ask people sitting or standing next to me if they liked jokes and wanted to hear one. Then I’d acknowledge that I wasn’t too good at telling jokes and ask for their opinion on whether the joke was funny or not. No matter how bad I was at telling a joke or how lame the punchline, it always got a conversation started when the other person proceeded to share a joke they knew with me.
Comment on a mutual observation or experience.
Another easy way to start a conversation with someone is by simply making an observation or sharing an experience. Most people open with a comment about the weather. It’s cliche, but it works and can lead to a conversation about where someone is from or what kind of weather he or she is used to and before you know it, you’re talking about favorite vacation spots. Or say you’re standing in line waiting to order coffee when someone causes a huge scene that has everyone’s attention. Naturally, everyone will be looking around to see if anyone else saw what they saw, so when you make eye contact, you can say something like, “So, that just happened” and you can take it from there by using a combination of any of the above conversation starter tips or sharing similar experiences with unusual outcomes. Sometimes people end up swapping stories to pass the time by while waiting in line.
Open with a little humor.
So this one has yet to be tested, but it’s one I would totally try out just for kicks. I actually read this one online and thought it was super unique, but in order for this one to work, you need context. This is one I could have tested when trying to start a conversation with one of the burlesque dancers already engaged in a conversation with a couple other people, but again it’s all about context and depends on your personality type, how many people are involved in a potential conversation you’d like to start or jump into and whether or not you know anyone. Okay, I’ve created enough suspense by now. When you see two or more people talking to each other, you can saunter over nonchalantly and make a simple, yet humorous request:  “Hi, I’m Niki. Can I get tickets to this conversation?” If you want, you can add in the word “because” and explain why you’re interested in joining the conversation. For example, “Because with all the flying hand gestures, I’m really curious to know what you all are talking about.”
So there you have it—six simple ways to start a conversation with just about anyone. Practice with people you cross paths when in your everyday life and it’ll get much easier when you happen to cross paths with an uber hottie. You’ll come off as a natural no matter how nervous you’re feeling on the inside. With these helpful tips, you can start conversations with perfect strangers like a pro.
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