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I started conversations with 10 strangers over a month to gain confidence in my dating life. Here are my biggest takeaways.

Dec 6, 2023, 17:53 IST
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  • When it comes to flirting, I've always lacked confidence.
  • I wanted a way to challenge myself and get out of my comfort zone.
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Normally, if I have a crush or want to approach someone, I tend to become shy around them. My gut instinct is to turn the other way and not look at them. Instead of trying to find a partner in person, I have used dating apps, which help because you know the person you are messaging is already interested in you.

However, I have found I easily get burned out on them, due to their repetitive nature and how easy it is for people to ghost. To overcome my shyness and try in-person dating, I made "dating business cards" to give out. They had a cute design with my name and number on them, and I thought it would be easier to give people my information this way than verbally. But I didn't follow through because I was still too anxious to approach people and hand them out.

After that, I gave up on dating for a couple of months to take the pressure off. Then, I stumbled across some videos from Lily Womble, a dating coach on TikTok. She gives tips on in-person dating, including accepting the messiness, celebrating yourself, and challenging yourself to say, "Hey, how's it going?" to more strangers.

In talking with friends, I've learned I'm not alone in my struggles. Other people tell me they're also often too intimidated to chat with people. I wanted to find a way to build my confidence, so I decided to take on Womble's challenge. I put myself out of my comfort zone to see whether I could get used to talking to people I didn't know by saying hello to 10 strangers over the course of a month. While her advice is about talking to strangers you're attracted to, I decided to practice by chatting with just about anyone I saw in public when I felt like there was an opportunity for conversation.

I wanted to get out of my comfort zone

During the experiment, I learned that "hello" or "how are you?" often didn't work as conversation starters, especially if I spoke when walking past someone on the street. Despite largely being ignored when I tried these simple greetings, making an effort still felt better than ignoring others and looking at the ground. And occasionally, it did work.

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Once, I said hi to the person delivering my groceries, and it opened up a conversation about what we were up to that day. On other occasions, I chatted with people I saw in shops. I gave one person a compliment on their glasses. Another time, I received a compliment on my favorite jumper, which is covered in chipmunks.

This small talk may not seem significant, but because I work remotely, it gave me moments of connection that brightened my mood for the rest of the day.

I happened to start my experiment in October, and it turns out that a Halloween maze is an excellent place to talk to strangers. Your adrenaline levels are up, and you aren't thinking about what you're doing aside from looking out for the next person who'll jump out at you.

I took this opportunity to strike up conversations with other people there. I chatted with strangers about how scary the maze was compared with others I'd been to. And when someone got separated from their friend group at the same time I did, we helped each other out.

I've realized that talking to people I don't know isn't as scary as it seems

Throughout the month, as I had conversations with people I normally wouldn't talk to, I realized there were plenty of opportunities around me for connection that I often passed up.

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At an appointment, I watched as the receptionist chatted with everyone who walked past. When she talked to me, I extended our conversation by asking additional questions — something I normally would have avoided — just to enjoy the interaction. I've realized that these small moments are what create community.

I see this challenge as a success. It was a baby step to get used to putting myself out of my comfort zone and celebrating myself. My favorite conversation starter was giving people a compliment — it felt like a natural way to begin talking to someone that would hopefully make them smile, even if the encounter didn't continue.

This challenge also made me start to face my fear of embarrassment and rejection. Even if I didn't get the response I had hoped for, it was fine — I'd survived. I hope to apply this realization to in-person dating. I know that even if it seems scary, if I get rejected, it's not the end of the world. It's just a small moment in my day.

My experiment is a reminder that if I keep looking up and interacting with the world, it will benefit me in so many ways — it can improve my confidence, boost my mood, and help me make connections. Maybe one day, I will even feel confident enough to ask someone out on a date.

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