23 Ways To Strike Up Conversations And Kill Awkward Silences

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