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I dunno … the way you describe it sounds very forced and awkward. If you don’t have anything to talk about that comes up organically, then maybe they are not meant to be friends.
Yes!
A typical relationship goes as follows;
Small talk – fact disclosure – opinion disclosure – emotional disclosure
Since you are acquaintances, you have passed the small talk phase, now it’s the time to express details of your life that make you interesting. Additionally, showing interests in their life can be in this field. This is where you find similarities and humans thrive on being similar. Once you find things that you like together, plan an outing for that interest. That way you can do more fact/opinion disclosure and move up to emotional disclosure.
Sometimes you just have to bring up a topic or something of interest. It doesn’t matter what it is. By bringing different things into the discussion it can lead to deeper conversations and you learn more about a person.