One of my most awkward conversations happened when I was a shy, 16 year old girl.
I’d just come back from a Caribbean cruise with my parents where I’d met this cute boy who lived a few towns over. He and I had exchanged phone numbers, but a week after the trip I still hadn’t heard from him and was determined to do something about it. So, for the first time in my life, I mustered up the courage to call a boy I liked.
My heart was pounding as I slowly dialed the number. The phone rang, and he picked up.
“Hi, it’s Camille. From the cruise.”
And then… nothing. I’d planned out how to say that first sentence ever so casually – but had no clue what to say after that.
After about 10 seconds he stepped in to fill the space. “Well, um, I have to go eat dinner now. Bye…” And hung up.
I was mortified. I listened to the dial tone for a few seconds, then vowed to never put myself in that position again.
If I was going to make the first verbal move with anyone, I was going to learn how to do it right. And that included not just how to start a conversation, but also steer it into a natural flow that’s enjoyable for both people.
Over the next ten years, I continued to push the limits of my introverted nature by having conversations with people I didn’t know, in all different kinds of situations: elevators, networking events, in line at the grocery store. Everywhere.
Hundreds of random conversations later, I discovered two key factors in how to have a great (i.e. comfortable and non-creepy) conversation with another person, no matter the topic.
#1 Take the lead
Assume the person you’re engaging with has never had a random conversation in their life, and be prepared to steer it yourself by introducing a topic you can both relate to.
That could be asking where the woman next to you on the train found that amazing argyle scarf, and discovering you both share Scottish ancestry.
Or comment to the guy on the escalator next to you on what a beautiful day it is and how summer is your favorite season.
#2 Give the person some space to come to you
People who don’t know you need to feel safe in taking the risk to engage by feeling free to opt-out of the interaction without fear of awkwardness or causing an embarrassing scene.
Maybe you could compliment your frazzled-looking coworker on her beautiful new earrings before continuing your walk down the hall. That’s just enough to make her feel good without pressuring her to engage with you in the middle of her crazy workday.
Or you could ask “How’s your day going?” to the guy who caught your eye in the grocery store produce section, giving him the option to respond in more detail if he’s interested in engaging, or just with a simple smile if he’s not.
No matter how old we are, it can be scary to engage with another person when we don’t know how they’re going to react to us. Throw in feeling some level of attraction to them, and / or having it happen in a public place, and it can be absolutely terrifying.
So, start engaging with people you aren’t necessarily attracted to. Thank the elderly gentleman who held the door for you – or hold the door for him and tell him you love his bright pink bowtie. Ask your pharmacist how her day’s going by looking her in the eye, smiling, and letting her know you’re truly interested.
After you get enough random interactions under your belt, work up to people your own age and eventually the gender you’re attracted to.
Conversation skills are just like a muscle – the more you work them, the stronger (and more attractive) they get!
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