by Niall Doherty

A friend recently emailed saying he has the following challenges when it comes to conversing with strangers:

– Difficulty initiating. I have no idea how to open. I always feel stupid asking stuff that activates the rote responses we always give.

– I don’t know what questions to ask. I know it’s about listening and asking questions, and not so much about me talking, but I’ll listen, and then when they stop talking, I don’t know what the hell to ask.

I’ve struggled a lot with this kind of thing in the past, but I’ve worked on it over the years and have become quite comfortable and competent. Put me in a room full of strangers nowadays and I’ll usually have a great time and make a bunch of new friends.

Here are a few tips I sent back to my buddy, plus additions. You might find them helpful.

Initiating

1. I often just walk up to someone, offer a handshake and say, “Hey, we haven’t met yet. I’m Niall.”

2. Another one I use regularly, if I’ve seen the same person multiple times but haven’t spoken to them yet: “Hey, I keep seeing you around, must be sign that we should meet each other.” I used this a couple of weeks ago at a social event and ended up chatting with the guy for fifteen minutes.

3. Use observational openers. Look for some interesting piece of clothing the person has and ask them about it, or ask what they think about the venue. I remember chatting and laughing with a group of Brazilian dudes for several minutes at a crowded night spot I went to all alone on Saint Patrick’s Day 2012 in Dubai. I was walking past them and noticed they were all ridiculously handsome, so I used that observation to strike up the conversation: “Sorry guys, I have to ask, what’s going on here? You’re making me feel ugly. Are you like a modeling troop or something?”

4. More of a cheeky one, can work well when flirting if you’re confident and relaxed. Approach a girl and ask if she’s seen Brian. She’ll either say no or ask who Brian is or just look confused, and then you crack out a smile and say, “Actually, I don’t care where Brian is. I just wanted an excuse to come talk to you.”

5. If you want more examples of flirtatious openers, check out the SimplePickup guys on YouTube. My big takeaway from them is that you can say/do pretty much anything as long as you have a fun and confident vibe about you.

6. Another opener I’ve used many times, mostly in bars or other nights spots when I’m alone: “Hey, my friends aren’t here and you people look fun. Mind if I join you for a bit?” Or a variation that I used a few months back at a food court in Chiang Mai (ended up sitting and chatting with a big group of expats for a half hour): “Hey, would you guys like a new friend for a bit?”

7. Build momentum. I don’t usually feel very social right off the bat. I often need to “warm up” a little. You can do this by starting off chatting with hired guns (bar staff, waiters, etc.). They’re paid to be nice to you, so it’s not too hard to get a friendly response and make small talk with them. Then you can move on to low-risk openers.

8. Low-risk openers don’t require much response from the other person. You’re just giving them a “by the way” comment. For example, you can stop off on your way to the restroom and say to someone, “Hey, I was just passing but had to stop and say that I love your jacket. Where did you get it?” If the response is cold and short, you can exit gracefully with something like, “Okay cool, thanks. Have a good evening.” But if they respond warmly, you can stick around and take the conversation further.

9. Open with a genuine compliment. A few months back at a breakfast meetup I approached a guy and told him I was jealous of his tan. We hit it off, he invited me on his podcast, and now we’re planning to hike Machu Picchu together in March.

Awkward silences

10. Work on ending conversations better. You don’t always have to keep it going. You can always just say something like, “Well it was nice to meet you. Hope to see you again.” then shake their hand and walk away confidently. Don’t even feel like you need to give an excuse for ending the conversation. But don’t just walk away from them over to an empty space either. Walk with purpose into another conversation or to the restroom or wherever.

11. Keep your sense of humor and actually comment on the stalling/awkwardness. I love doing this. If someone gives me a one-word answer that effectively kills a conversation thread, I’ll often say, “Oh, well I guess that’s the end of that conversation! How about another?” Then after a laugh you talk about what to talk about 😛

12. Always try ask people how they feel about things. If someone tells you they just quit their job and they’re not quite sure what to do next, ask them how they feel about that uncertainty. Is it scary? What you’re trying to do here is deeply understand what their experience is like. As Stephen Covey once wrote, “the deepest human desire is to be understood.” If you can help people express themselves and feel understood, they’ll warm up to you fast.

13. You don’t always have to ask questions. Make statements. Often you can ask a question in the form of a statement. Example: “You must have a lot of experience with that.” Then that’s their cue to tell you about their background. Or like this: “You seem very comfortable in this environment. I’m guessing you’ve been here before.”

14. Make the silence the thing. When you notice a conversation stalling, actually tell people that you’re working on becoming more comfortable with lulls in conversations. Ask them if they can help you practice, and then see if you can both go twenty seconds without speaking or feeling awkward. Make it a game.

15. If someone is very socially smooth, ask them if they’ve had to work on that and tell them you admire how they handle themselves. Ask them what advice they’d give to someone who is trying to get better. People love being complimented.

16. I learned an interesting trick from Nick Sparks in this speech (near the start). He calls it, “teaching her how to have a conversation.” It’s mostly for pickup, but I imagine it could work well even when you’re just being friendly. Basically you initiate the conversation very simply and then when there’s a silence you give them a look that says, “Well, what have you got? I’m waiting here for you to contribute to the conversation. Don’t you have anything interesting to say?” I haven’t tried this myself yet but it sounds pretty solid, and I’m sure you can pull it off in a curious way, rather than it seeming like a dick move.

17. Be genuinely curious about the other person’s experience/job/hobby. A good fallback question to ask when you can’t think of anything else: “What got you into that?” or “How did that come about?”

18. Get good at telling stories. Everyone loves a good story or amusing anecdote. With practice you can turn pretty much anything you experience into an interesting story. One I’ve used a few times here in Korea is my frustrating (but kinda funny in hindsight) experience of trying to get a SIM card. If I’m chatting with another expat and there’s a lull in the conversation, I’ll ask if he/she had any trouble getting a SIM card here, and then I’ll share my experience. Try out different stories and see which ones work best in conversation. Work on improving how you tell them, like a stand-up comic would work on his routine. Toastmasters is a good place to practice. After a while it will come naturally to you and you’ll be able to tell a good story without much forethought.

General principles

19. Try to acknowledge everyone. That guy you met at the party last week? Make a point to catch his attention and banter for a bit when you see him at the mall. The girl in the park you recognize but can’t quite place? Say hello anyway and ask where you know her from. The one person in the group you haven’t met yet? “Hi, we haven’t met yet. I’m Niall.” Especially in a social setting, like at a networking event or a party, go out of your way to meet and acknowledge as many people as possible. Avoid rubber necking though. Give your full attention to whoever’s in front of you and stick with any conversation you find interesting.

20. If you’re very shy, practice as much as possible and accept that you’ll probably suck at this for a while. But rest assured that you’ll definitely get better if you stick with it. It’s just like exercise. At first you’re out of shape and the workouts are painful, but after a while you start to feel better and lifting those same weights begins to feel like a breeze. Remember, you gotta feel weak before you feel strong. Most people never overcome shyness (or get in shape) because they’re unwilling to endure the pain period.

21. Have fun. If you can bring a fun vibe to an interaction, people are going to respond better to you. Relax, assume rapport, crack silly jokes, self-deprecate, make funny observations. Humor is a skill you can improve. Study stand-up comics, take an improv comedy class, hang out with funny people.

22. Reflection is also key. Think back on previous interactions that you wish had gone better and do them over in your head. I used to take this to the next level and actually write out the scene as I wish it had unfolded. Doing this gives you a much better shot of handling similar situations comfortably in future.

23. Introduce elephants.

Try out some of those suggestions and report back in the comments. I’d also love to hear some of your own tips for being social.