This post is part of my 90 Strangers In 30 Days series. Also check out the project hub pagerules and introduction post, project recap, my five biggest takeaways, and the popular reddit post

Over the years, I’ve received countless questions about 90 Strangers In 30 Days and social skills both in person and via email. 

I am always flattered to receive these (send me one!), but also thought it might be helpful to list answers to some of the more-commonly asked ones here. Shorter answers to questions from the more immediate aftermath of the experiment can be found on the project recap page.

+ What is 90 Strangers In 30 Days?

In June 2013, I did a social experiment I made up called 90 Strangers In 30 Days. The project was well-received on reddit and based on the many comments I received from readers saying it helped them improve their own social skills, it was clear to me that this was a message people wanted to hear (and an issue people wanted addressed). I’m working on other ways to expand and explore this idea further (such as the TEDx Talk I gave and the manuscript I am shopping around).

+ What do you suggest I say to random strangers?/What’d you do to start a conversation?

If thinking of what to say is challenging for you, make it easy on yourself and don’t focus on starting a full-blown conversation at first. Instead, just focus on making good eye contact with people and giving them a simple greeting like “Hi, how is your day going?” While this might seem counter-intuitive to starting a quality conversation, in the beginning this is an easy way to make both yourself and the other person comfortable before sliding into talking about something else. You may even find that you rarely even need to say much else to start a conversation with someone.

Once you get comfortable with this kind of simple greeting (cashiers are perfect practice for this by the way), from there you can build and challenge yourself to greet people with something other than “how are you?” A list of the things I said to start conversations during my 90 Strangers run can be found here. Generally, I started them one of four ways:

1) Making an observation: Throwing out a comment about something going on around both of you, about something they are wearing, and so on. I’m a big fan of starting conversations this way simply because it gives the conversation a direction at the beginning that isn’t an ‘interview’ (e.g., where are you from, what do you do, blah blah) and is something both of you can relate to together. Once you exhaust talking about whatever the observation is, it then often feels more natural to slip into typical conversational meet and greet questions.

2) Paying a compliment: A completely underrated way to start a conversation and to me, one of the easiest. The summer after 90 Strangers I even did a similar experiment where I paid 90 Compliments to people in 30 days. 

3) Asking a question (beyond just “How are you?”): Could be anything from “Where did you get that shirt?” to “What beer is that and what do you think?” to “What do you cook with that?” Unless it’s a more abstract question (“Did you hear about X?”) these obviously have a lot of overlap with observational openers. 

4) Introducing myself: The majority of conversations during 90SI30D I started with a simple ‘Hi, I’m Andrew.’ These were mostly used in more social settings such as small parties, group fitness classes, social dance events, and sometimes even bars. More often than not, that’s all it took to start at least a halfway-decent conversation.

I’ve written a little more about starting conversations here.

+ I don’t have a hard time starting a conversation but I just can’t think of things to say to keep it going?

This was a roadblock of mine for a while, too. An idea that helped me to keep conversations moving is called ‘threading’ (not my original concept by any stretch). Basically, during the course of a conversation different ‘paths’ or ‘threads’ will present themselves to you in the form of certain keywords that the other person says. From there you can pick out ones you are either curious or knowledgeable about and move the conversation in that direction.

For instance, if someone said to you “Man, I am exhausted, I was out late last night with friends and the night before I just got back into town on a red-eye.”, you could choose to ask about their night out (“Where did you go out to?” What was the occasion?”) or his travel (“Where did you just get back from?” “Work trip or just for fun?”) or you could opt to share a related story of your own (if it’s relevant to one of those topics).

I actually wrote briefly about this a while back here in my Anatomy of a Conversation series.

Many of the same ways you could open a conversation are also good ways to keep one going. For instance, making observations provides plenty to talk about and is something you can both relate to in that moment. I’ve also learned that you can ask questions pretty much all day long (figuratively) and people will usually walk away thinking you a great conversationalist. When you become genuinely curious about everything and everyone in the world, you’ll never run out of things to talk about.

+ How did you begin your “campaign” to overcome anxiety and social phobias? Did you seek professional help and then go from there? Or was it all self-help, reading e-books, etc? In the age of info-overload, I’m having difficulty wrapping my head around a good plan of attack…

For a period of two-to-three years I read every piece of advice online about how to talk to strangers and improve social skills. A lot of that was absolute crap, but this search did lead me to these three books which we particularly influential: 

1) How To Win Friends and Influence People by Dale Carnegie: The advice is a little sales-centric, but it’s amazing how differently the world responds when you put these seemingly simple principles into action.

2) Models by Mark Manson: It’s geared toward dating, but from the angle that to be awesome with women, you have to first make yourself into an awesome dude that you love (without being woo woo about it). Funny enough, if you are extremely secure in your own skin, you’ll find that you will no longer sweat talking to people anymore.

3) Quiet: The Power of Introverts In A World That Can’t Stop Talking by Susan Cain: I’m someone that needs to know the why of things, which makes this probably the most important book I have ever read: it was the catalyst that once and for all shook the shame I had about being an introvert, while at the same time debunking the false beliefs I had about introversion and shyness. After reading this I finally realized that nothing was “wrong” with me, I (and more others than that would admit) are just wired differently. Cain also did a TED Talk that basically serves as a CliffsNotes version of the book.

But an ounce of action is worth a ton of theory, and the biggest ROI for improving social skills comes from forcing yourself into social situations that make you uncomfortable. What worked best for me was to set a “quota” each day and just try and start interactions with X amount of people, even if it’s just one a day at first, then build from there. I also can’t stress enough the role that hobbies played in breaking me out my shell: putting myself into situations with people I didn’t know, yet I automatically had something in common with (our mutual interest) was huge for me and showed me that I could be competently social if I cared what was being talked about. 

Beyond that, it all came down to pushing myself to talk to more people and constantly analyzing (often overly-so) pretty much every interaction I had, every day, and making note of how people responded to my social ‘advances’.  

I also wrote a post about dealing with the advice overload that comes with trying to improve your social skills.

+ On those days you were feeling apathetic/unmotivated, how did you push yourself to continue on with the challenge?

There were two main ways I overcame apathy on the days I just wasn’t feeling ‘it’:

1) The first was to consistently try and put myself in places that both had a lot of people around and where I felt comfortable. Wanting to be somewhere allowed me to focus on something besides just ‘ok, I could go to talk to that person and say this…, or what if I said this…” but instead on the activity at hand, which gives you plenty to talk about and comment on more naturally since you know you and the other person likely have at least one thing in common (the interest). For me, this ‘easy’ place was the gym but it could also be some sort of activity club, MeetUp group, shows, etc.

2) Once I got a few days’ worth of starting conversations under my belt, it became easier to use those as reference experiences. Thinking back to even the interactions that didn’t go anywhere reminded me that nothing truly bad is going to happen just by trying to talk to someone (even if they’re not receptive). It also allowed me to think things like “no reason to feel nervous about starting a conversation in a grocery store, you’ve done it before, just do X like you did that one time” and conversely what NOT to do in certain situations, both of which made me feel more confident. And like with anything, practicing and momentum (mostly) made each conversation I started easier than the last.

I’d say it’s also important to ask yourself why you’re apathetic—just don’t want to leave the house? (see #1). Is it anxiety-related/discomfort around talking to new people? Severe edge cases aside, that mostly can be cured by practice and continually forcing yourself to do the uncomfortable. Tracking your results someplace tangible (even just a notebook, calendar, or spreadsheet) can be a powerful tool to keep you motivated as well—once you get a streak of three or four days going you, won’t want to suddenly have a gap in your log! I first learned about this strategy in this post about Jerry Seinfeld of all people. 

+ Since you’re more used to talking to people, do you actually enjoy it or does it still feel like a drain?

I definitely still love talking to and meeting new people and thankfully it takes considerably less conscious effort than it used to. However, I do find that sometimes I get lazy and don’t put myself out there in certain situations because I no longer have that burning urge to prove to myself that I am a social person. Essentially, it’s “I could start a conversation with this person, but I just don’t feel like it.” 

That’s not to say I think I should be talking to everyone that crosses my path all day, every day—I’d get nothing done and be exhausted by day’s end. However, there are definitely still moments where I could have had a potentially interesting conversation with a bystander but I never made the move (regrettably). 

+ When you went out to bars, events, etc., where you alone or did you have at least one friend with you in case things got awkward? I’d like to start going out more often in order to make some new friends.

I would say that your focus when going out should be less about just “making friends” and more on just having meaningful conversation and connection with people. Friendships are something that can’t really be forced and often are the result of nothing more than shared interests and frequently occupying the same space (think college dorms). At least for me, 90SI30D was more about developing the skills that would help me better capitalize on situations where I was around people that I ‘vibed’ with naturally and could eventually become genuine friends someday. 

When I did the experiment I think for the most part I was alone during most of the interactions. Even if I went to a bar with friends, it was easier for me to start a conversation when say, I was at the bar grabbing a drink or doing something else away from the friends I came with. For me, being by myself would “scare” me into starting conversations because talking to people made me less anxious than just standing alone by myself. When you are with someone it can be easy to just rely on them for conversation and it can be much harder to put yourself out there.

+ Why do you get so fired up about social skills?

Extreme shyness and social anxiety were things I eventually learned to overcome in my early twenties after feeling like a spectator to my own life. I don’t believe in the ‘it’s just something people grow out of’ attitude society has toward withdrawn individuals; social confidence is an important skill-set that can and should be taught as early as possible.

My quality of life has skyrocketed since I learned to come out my ‘shell’, and whether someone picks things up naturally or they had to read a how-to book, they are skills everyone deserves the opportunity to learn.

Want to try 90 Strangers In 30 Days for yourself?