I saw that guy on Facebook and I texted him like "Hey, nice hat lol" (Okay, don't judge me, I know I suck at this) and he replied "Lol yeah but it's not mine lol" And then we exchanged the ordinary questions "What are you doing, where are you from and have you ever been in the city I live" (we live in different cities, far away). From now on I don't know how to keep the conversation going right.
So I need your advice on this, I don't want to bore him with questions like "yo what's your favorite color". I want it to be kinda interesting conversation, ideas?
Most Helpful Guy
If you're stuck, ask the golden question or a variation of it. "Tell me more about that." This is brilliant because not only is it continuing the conversation and opening up tons of opportunities for more conversation but it shows that you're genuinely interested in what he's saying and you're also letting him take the conversation in whatever direction he wants. When he told you that the hat wasn't his, you should've asked him who's was it and then asked him about the story behind it. That would then open up lots of different conversation paths. You could pick out bits of the story and ask him about them in more detail, possibly opening up more stories. It's actually not that hard. So always look for more detail when he tells you something.
Hope this helps :)1
Most Helpful Girl
When he said the hat is not his, you could habe said "whose is it? Maybe you should geht one cause it looks good on you".
Just find something to ask or say based on what he said. And if anything random occurs in your mind, ask him. Ex: "Nicki minaj, hot or not?", "do you like the 90s/80s/00s fashion/music?"
Just talk about anything! Share interesting stuff you find on the internet. Then you can discuss about it. Open up to him a bit.
It is, however, a 2 man job. He also has to habe the personality for it. It he's the type of pea-sized boy who only gives yes or no answers, don't waste more of your time and just move on0