Want to improve your social skills?
Talk to strangers.
If you learn how to talk to strangers, you can talk with pretty much anyone.
Now here’s the “secret”:
Not all strangers are made equal.
Some strangers are just a lot less intimidating to talk with.
Enter rideshare drivers!
Their job is to make sure that you have a smooth experience, after all.
As someone who doesn’t drive — yep, I’m that lazy — ridesharing is how I get around anywhere for the most part, and that’s how I ended up chatting with hundreds of drivers.
Based on my experience, here are a few tips that have worked best. You will notice that most of these tips are really, really simple, and I will explain why that’s the case.
Say hi and smile
A big mistake most folks make is skipping the small talk, or trying to be too clever in small talk.
Yes, you can be creative, but when you’re nervous, it’s way easier to keep things simple and direct.
Saying hi also helps you gauge early on if they are open to chatting a bit more.
Comment on their day
Another way to test if they’re open to chatting?
Ask them about their day. There are many ways to go about it. You could comment on their day, the traffic, or the weather:
- “Busy [morning/afternoon/evening] so far?”
- “Wow, didn’t expect that much traffic today/tonight.”
- “Looks like it’s going to rain again…”
If they brush off the comment, that’s OK — it might have been a rough day for them (this ridesharing business ain’t walk in the park!) As Martin Dulberg, a veteran Uber driver, commented:
“At this writing I have a 4.96 rating and roughly 14K rides under my belt… What I have noticed over the seven years is that riders have come to take the service for granted and have way higher expectations than what they are paying for.”
Ask what their name is
If they have a name tag, ask them how to pronounce their names correctly. (Exception: if the name is a simple one like John…)
- “How do I pronounce your name?”
- “[their name] – did I say it right?”
You could follow up by asking “so what does your name mean?”
Compliment their car
Most rideshare drivers take good care of their cars. A simple compliment could be: “Wow, you sure keep your car clean!”
If you want to be playful, you could say something like:”Gee, your car is a hundred times cleaner than my room.”
Even if their car isn’t in the best shape, drivers usually personalize their car one way or another. I’d pay attention to any of the following:
- If they have any windscreen or bumper stickers, for example a Starbucks drive-through sticker
- If they have a cool car dashboard, rearview mirror or rear deck accessory
- What number their car’s license plate is (especially if it’s unique)
- What color their car’s paint is (especially if it seems customized)
Here’s how to compliment their car without being awkward or creepy:
- “That’s a cool [sticker, accessory, etc.]!”
- “I wish I had that [sticker, accessory, etc.] in my car too.”
- “I love your car’s paint color – it’s so pretty.”
Compliment them personally
Make sure that you’ve already got them chatting — you’re in a small space together and it can come across as intrusive. And, I wouldn’t compliment their appearance unless you’re trying to flirt 🙂
Here are other things I’d look out for instead:
- If they’re wearing an interesting personal accessory, for example an old watch or a colorful brooch
- If they have tattoos (tattoos are typically imbued with meaning)
Ask them about their driving experience
If they have been open to some small talk, try going a bit deeper by asking them about what got them working here. Here are questions you could ask, depending on the level of rapport:
“Small talk” questions
- “Do you drive full or part-time?”
- “Where were you driving from?”
- “How much do you drive every day?”
- “How long have you been driving [Uber, Grab, etc.]?”
- “How is it like driving in the city/town?”
Deeper questions
- “What’s your favorite part of driving?” // “What do you like the most about driving?”
- “What would make a perfect day/evening for you?”
- “What was the craziest customer you dealt with?”
- “What’s your most memorable experience/moment as a driver?”
Alternate between asking questions and talking, so that they don’t feel pressured to answer one question after another 🙂
Ask them non-work questions
Once they get comfortable talking with you, you can open up the conversation and start getting to know them personally.
There are too many ways to continue the conversation from here, so I’m not gonna try… but here are two helpful resources:
- Lists of conversation starters (organized by topic)
- 25 useful phrases to keep a conversation going (and avoid awkward silence)
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