How to Give a Stranger a Conversation Hook

I live for great interactions with the people around me. When I'm in my own head and not interacting with people, I get quite depressed and feel super isolated-- which made the week I was sick with the flu and could barely get out of bed yet alone pick up my phone the loneliest week I've had in a long while. I'll gladly mingle at parties and sit down for coffee or tea (usually tea; I love a good Oolong) and get to know someone better.  I like my time alone, but when I'm with people I'm WITH people. When I do host parties I love being the social connector, and I can usually be quick to make the connections between people that should meet sooner rather than later (I've definitely been to a networking event, talked to one person, then talked to another person and realized they should talk to the first person I talked to and got them introduced right then and there).

I'm a huge lover of DMC's (deep, meaningful conversations) especially with people I don't know yet.  I'm realizing as I meet more and more people that I'm actually less awkward than I thought I was by going up and talking to people just because I'd like to and am usually not afraid to butt in with some finesse.  Today I'd like to talk about how to do that a little better.

First, a slight disclaimer: Everyone has their own way to socialize, and I fully recognize that the way I socialize is not the same way others want to socialize.  That said, I want to encourage you to get a better feel for how you want to show up in social settings and what's in line with your personality for socializing. I tend to be a social butterfly that flits from conversation to conversation, not getting too intensely deep with any of them unless one of my natural conversation hooks gets sunk and we end up dropping into conversation fast.

A conversation hook is a question or statement that connects the person to your interest, lights them up, or gets them to open up and sink into the conversation with you more.  I used to use them all the time and accidentally force the situations with whomever I talked to, but as I learned to troubleshoot my conversations I realized that not everyone wants to sink into conversation. In fact, though I tend to make many people comfortable talking to me, there's some people that just don't want to talk a lot.  Some need a social activity that connects you to them first, like dancing or a game. Some have social anxiety and can't have deeper conversation with a new person even if they want to. Some just don't have any idea how to even start talking about something with someone they don't know and need lots of encouragement (which isn't always easy). Some people just are in a different headspace and don't want to talk.  All of these are okay! But putting conversation hooks out there to let someone choose to sink with the topic is huge because it allows them to decide if they want to go deeper with the conversation or not.

How do you deliver a conversation hook to a new person?  Well, since I already am running with a fishing metaphor, I'll keep going: usually by picking a spot to fish first.

So let's say you're at a party and don't know too many people there. I'll usually look around and take a look at body language.  If there's individuals that seem closed off and in their own world, I'll usually leave them alone for now (but I love talking to wallflowers and may say a few words to them later, just not right off the bat because oftentimes conversation doesn't get far until later after I've talked to a few people). If there's a group of people talking but they seem to be closed off from anyone entering the circle, I'll stay away from that too.

That said, if I see an individual looking around, trying to make eye contact, or maybe awkwardly standing next to a circle seeming to try to engage, that seems like a good person to talk to and that's open to conversation.  If I see a group that's talking with each other and have some body language facing outwards a little bit that would make it so that another person can just pop in and add to the group without the physical position I'm in being too far away from the others, then I'll go up to that group.

Now what?

If an individual, I'll start with "Hey! I don't think I've met you before. I'm Sam." Yes, it's really that easy. Just walk up and talk to the person.

If a group, I'll stand there and say to the group and the person that might be talking, "Hey, is it okay if I join you guys in conversation?" And assuming they say yes..."Great, thanks! By the way, I'm Sam."

Neither of these are hard to do. Neither of these are awkward to do considering the circumstances. There may be some hesitation because 1. The individual seems to be interested in something else other than you, and 2. The group is in the middle of conversation and you're interrupting it.  In general, both of these are okay to do.

Let's run with the individual first. You've introduced yourself, they introduced themselves, and now you can run in any direction you want now that their attention is on you.  Now is the perfect time to... ask a question and listen!

A couple things that I use as openers from here are:

1. "So what brought you to this party? I don't really know anyone here save for like 3 people."

2. "It seems some people are coming from a bit of ways away for this. Are you local?"

3. "So what do you do for fun other than going to (insert general term for what event you're at)?"

4. "Admittedly I don't know too many people here. Do you know anyone else here other than the host?"

5. (This works better for me just because I'm a woman, but I've seen men and non-binary people pull this off well too) "I really like that (something that they're wearing that catches your attention)! Where did you get it?"

I like these openers because these in themselves are gentle, seemingly-small-talk questions that can be surface-level and have a friendly little chat, but they also allow for deeper conversation if the person wants to do that. They're a really good way to get a feel for if the person is receptive to talking more about themselves.  The answers that they give for their answers can lead to more conversation hooks. Here's an example of a conversation I had with a woman at a social networking event not too long ago:

Me: That's a lovely bracelet! Where did you get it?
Her: Oh! Thank you! My friend got it for me when she went to Nicaragua.
Me: WOW! That's incredible. Will you be going there or somewhere else soon?
Her: Oh, I'd love to, but it'll be a while before I can. But traveling is something I really want to do more.
Me: That's so interesting. What's the place at the top of the list?

Now, something to consider here: I would not have talked about travel more if she didn't seem that interested in talking about Nicaragua in the first place. If she mentioned more about her friend getting the bracelet for her, I would have said something about the friend that bought it being a good friend to bring something back for her and gone in that direction.  If she mentioned the name of the store with excitement, I would have either talked about a shared experience if I knew of the store or I would have asked about the other things at the store if I didn't know of the store. How people respond to your opening questions helps you make conversation hooks that are relevant to conversation.

Another person I talked to this weekend at a party turned into a lovely conversation (paraphrased slightly):

Me: So what do you do for fun when you're not at Goth Parties?
Guy: Hrm. Other than drinking... I really like rock climbing!
Me: Oh! Admittedly, I'm really terrible at that, but I know there's a few places around here. What do you like about it?
Guy: Oh man! It's such a strategy kind of game. Yes, there's a physical aspect, but it's really just a giant puzzle to solve.  It's really a nice change of pace from what I normally do in physics but I really love puzzles and it's a different kind that I get to try to solve.
Me: That's so cool! I really like puzzles too. I'll have to give it a try again. Is there any advice you'd give someone that's starting out for it?
This guy got really animated about rock climbing when he talked about it, and we later went back to talking about his work in physics and what got him into it. He took that conversation and we got to turn it into something that he wanted to talk about and I got to also follow my interest in the topic as well (which was mostly directed at how excited he was about talking about it). We got a nice little DMC for the time we got to talk and it was super enjoyable and satisfying to get to know him a bit better.

Now, let's look at the group. You just asked if you can join them in conversation and they (presumably) said yes. You introduced yourself and went around the circle.  If they were already talking when you came up, this is a good time to go back to the conversation, which makes it super easy to contribute since you just showed up and they're already very aware that you're there and want to come into conversation.

Me: So good to meet you all. I didn't want to veer off the conversation though. If you don't mind me asking, what were you talking about before I butted in?
Someone in the group: Oh, we were actually just talking about the Green line and where the A line is now.
Me: Oh! Actually, I had a client that told me it got replaced by a bus now.
Someone else in the group: Wait, really? I didn't know that! Which bus?
Me: I honestly don't remember off the top of my head which one to be honest, but honestly I'm kind of glad they retired it. The Green line is so long! Did any of you have to take it to get here?
Another someone else in the group: Yeah, I did from Allston.
Me: Oh Dear. I hope it didn't take too long.
ASEITG: Oh, it did... it IS the oldest line in the country and it rides like it is!
*laughs all around*
Me: Well, if you guys could live anywhere in the city--and maybe not on the Green line, haha-- where would you live?

From here, these people have something to think about, and now I'll learn a bit more about them. The group may dissolve a bit from this and we may get into smaller group talks, or they may go back to talking about the Green line instead of taking my conversation hook, but I gave them the opportunity to go as shallow or as deep into conversation, and it happened naturally.

The basic idea to consider is: let people talk about what they seem to want to talk about and follow your interest in that area. Try to pay attention to specific interest and give a hook for them to take either as deep or as surface-level as they want. It's in their hands to connect with you, but by asking conversation hooks like this you can actually have really amazing and connected conversations with people you normally wouldn't.