The Small Social Risk That Pays Off Over and Over
be willing to make the first move
We’ve written a few times about how the science shows that we are actually way more likable than we think we are, and that our conversations with strangers tend to go better than we expect.
So all those times that we’ve felt anxious or awkward about how we’re perceived, or worried about what will happen if we talk to a stranger— it turns out that when we do it actually works better for us. Maybe these facts have even propelled us out our door and to a Skip the Small Talk. Great!
What I want to get in to today is how taking one small risk in social and romantic relationships pays big dividends.
Whether it’s connecting with a new co-worker who made a great joke in the meeting, fanning the flame with a new crush, or finding your dream rock climbing buddy, this tip will serve you over and over again:
Reach out first. Follow up first. Propose the next thing first.
A lot of promising connections fizzle not because either person was uninterested, but because both people were waiting for the other one to make a move. Neither person wants to seem more invested, so each of them takes the other person’s silence as evidence that the connection wasn’t mutual. Sometimes all that stands between “that person was cool” and an actual friendship is one person being willing to risk seeming interested.
And somehow, showing interest can feel like a huge risk:
What if they didn’t actually like me?
What if I come off pushy or clingy?
What if they have something they’d rather do?
What if I’m being too vulnerable too soon?
These are real concerns. Especially if we’ve had experiences with someone else being a bit much or giving us unwanted attention, we can become extra sensitive to the possibility of doing that to someone else.
And y’all, I am so serious: this is NOT an encouragement to send someone 36 texts in a row after meeting them for the first time. The difference between initiating and pressuring is what happens after you make the offer.
Think about how we treat puppies we don’t know on the street: “Can I pet your dog?” Bend down, extend your hand-- and let the pup approach.
Same thing with people, in spirit. You’re initiating the interaction, and they get to choose whether and how they respond. You can send the text, suggest a plan, or share something slightly vulnerable. Then you pay attention to what they do with it.
If they respond enthusiastically and help move the connection forward, great! If they give you a vague answer and never follow up, or you’re always the one reaching out and they rarely seem excited to hear from you, that’s useful information. Making the first move doesn’t mean taking responsibility for the entire relationship. It just means giving the connection a chance to become something.
Yes, there’s the possibility of rejection. There always is. And we’ve actually discovered together that we overestimate how bad rejection will feel.
For me, the feeling of sitting and waiting to see if someone is going to text me after we had a good friend hang, or a flirty message exchange on an app, is pretty stressy. Over time, practicing taking the risk of reaching out first has brought me a lot of relief from that worry. I’m no longer trying to interpret every detail of our last interaction or wondering whether I’m supposed to wait another day. I’ve done what I can. Now it’s up to them.
Let’s explore what making the first move can look like at different stages of a relationship.
Starting Out-- New Connections
With new connections, it’s all about breaking through the momentum of daily life. We’ve probably all felt it: you meet a cool person at a friend’s party, or match at a speed-dating event, and it’s hard to crack into each other’s established routines when you don’t already see each other organically.
The interaction may have been great, but then work gets busy, somebody goes out of town, and three weeks later it suddenly feels much weirder to text than it would have the next day.
You can make the first move before you leave the initial hang or in a follow-up message later. Be clear that you enjoyed the interaction. If there was something specific or remarkable about it, refer back to that, and suggest a time frame and activity.
Being specific helps for two reasons. First, it shows that you aren’t extending a generic invitation to anyone who happens to be nearby. You remembered something about this particular person and want to spend more time with them. Second, it makes responding easier. “We should hang out sometime!” leaves the other person with the work of figuring out what, when, and whether you meant it. “Want to go for a walk next week?” gives them something they can actually say yes to.
For example:
“Hey, this has been so great-- I’ve got to head out, but I’d love to continue our conversation. Want to go for a walk next week?”
“I can’t stop thinking about that lecture on the semiotics of 1980s comic books. Want to come to the tabletop game night at the comic book shop with me?”
“I loved what you shared at the writing workshop. Want to go to the next one together and grab tea beforehand?”
Going Deeper - Building Connection
We’ve definitely talked about how we can get stuck in conversational-- and relational-- ruts. Once you’ve established a connection, going first can mean offering a little vulnerability or asking a follow-up question about something the other person told you.
This doesn’t require jumping directly from “How was your weekend?” to your deepest childhood wound. You’re just making the conversation one degree more honest than it was before.
Small disclosures help because they give the other person permission to be a little more open, too. If you admit that you’ve had a weird week or that making new friends makes you nervous, they no longer have to wonder whether that kind of honesty would be unwelcome. You’ve shown them that it’s safe to move slightly beyond the standard “Everything’s good!” exchange.
A thoughtful follow-up question does something a little different: it shows that you were actually listening. Remembering that they were considering leaving their job or having trouble with a roommate communicates care without requiring either of you to manufacture a Serious Conversation from nowhere.
You should share, but give them space to decide how much they want to share in return. You’re opening the conversation, not requiring them to match your level of vulnerability.
That might sound like:
“I’ve been having kind of a weird week, actually. Nothing disastrous-- I’ve just felt a little off. How has your week been?”
“Okay, you’ve now told me three unhinged stories about your family. Are holidays with them as chaotic as I’m imagining?”
“I’ve realized I tend to pretend I’m totally fine when I’m overwhelmed, which is not particularly useful. What do you do when you’re stressed?”
“You mentioned last time that you were thinking about quitting your job-- have you gotten any closer to deciding?”
“I know we joke about both being terrible at dating, but I’m curious-- what are you actually hoping to find?”
They may answer in depth, give you a short response, or turn the conversation back toward something lighter. All of those responses tell you something about what feels comfortable in the relationship right now.
In fact, I try to frame it to myself as: “This is me getting information about how the other person is feeling about this level of vulnerability about this topic right now.” Not, “This is me getting information about whether or not I’m a normal, good, or lovable human.” Because if I think about it the other way around, every time I’ve not been excited about somebody inviting me to be vulnerable, it’s been way more about how I feel about that topic in the moment (or about how much time I have, or about who else at the party I want to talk to, etc.) than anything about the other person. And I think that’s the case for most people!
Integrating-- Building the Friend Group
Making the first move can also mean bringing people together.
Individual connections often need repetition and context before they begin to feel like part of your life. You may really like someone you’ve met twice, but if every hang requires one of you to arrange a dedicated one-on-one plan, it can be hard to build momentum. Inviting that person into a group creates more opportunities to see each other, helps them meet other people in your life, and begins turning a collection of separate acquaintances into an actual social network.
Organizing a group hang can also take some of the pressure off each individual interaction. No one person has to carry the entire conversation, and people have opportunities to connect in combinations you might not have predicted.
This doesn’t have to mean hosting an elaborate dinner party for 14 people. It can be as simple as texting three people you think might like each other and asking if they want to go to trivia.
A few possibilities:
Host a dinner party if you like cooking for a group. If you don’t, pick a theme and have everyone bring something: a family recipe, a favorite pasta dish, a dumpling, a soup, or whatever else sounds fun. A theme gives people an immediate subject to connect over, and almost everyone has some kind of food story.
Invite a few people to something you already wanted to do-- a picnic, a game night, a comedy show, or a trip to the farmers market. You don’t have to invent an entire occasion; you’re just turning your existing plan into an opportunity for more people to connect.
Choose an activity where the group makes or does something together-- whether it’s pulling black swallow-wort out of the ground in your neighborhood, building a little free library for your block, or sorting cans at the local food bank. A shared task gives everyone something to focus on, which can make conversation feel easier, and working toward the same goal helps people feel like a group instead of a random assortment of strangers.
None of these moves guarantees that a particular connection will grow. Sometimes someone won’t answer. Sometimes they’ll be busy, or the chemistry won’t be what you thought it was, or you’ll learn that you want different things.
But making the first move gives the connections that could grow a chance to do it.
So send the follow-up text. Ask the slightly more honest question. Invite a few people to do something together. You don’t have to push the connection forward all by yourself-- you just have to be willing to find out whether the other person wants to help.