I was walking to my nearby gym and on my way, I was walking towards this girl who was standing at the crosswalk.

I only caught a glance and she was cute. She was eating ice cream and it was cold outside. I thought about saying something like “aren’t you freezing?” in my head as I was walking but I just didn’t say it. The pedestrian sign then signaled and I just walked away.

I’ve noticed that I’m always hesitant to start an interaction with a stranger. The last time I did so, I asked someone what pants they had on and they were super disinterested.

2 comments
  1. You have set yourself a mental goal that you want to be better at socializing. Since you failed to take a step towards achieving this goal, yes you should regret it.

    However, don’t be so hard on yourself, it’s not a big deal. There will be many more opportunities to talk to strangers. I want you to regret it enough where that upsetting force will drive you to initiate a conversation the next time. If you don’t make it a regret you will always forgive yourself for not taking initiative.

    I often give my mentees the following analogy. Building up your social skills is like building up your physical strength. You cannot show up to the gym on your first week and bench 315. You first start with the bar and work your way up. Similarly, your social skills are best improved when build slowly and steadily. Start by asking random strangers for the time throughout your day. Once you get comfortable, proceed to ask follow up questions after asking for the time such as “what’s your name?”. Eventually you will find asking engaging questions to be very easy.

    Last note, don’t take anything too personal! When people give you a cold shoulder it’s very possible they are not having the best day. Just give them a smile and move on with your day.

  2. You shouldn’t regret it. Not everyone wants a stranger to talk to them. It’s possible she wouldn’t have enjoyed the conversation anyways.

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