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Like, “one time when I went to Japan” story, and “I went to Asia for a friends marriage” and “my most adventurous trip was…” story and more.
This date lasted 6 hours without one awkward silence.
Second, you’re not going to want to ask questions that can simply be answered with a “yes” or a “no” if you’re concerned with keeping the conversation going.
It doesn’t need to be a great effort or does it need to be as easy as leaving it to fate.
You just need to be yourself, have some depth in your conversation, and connect emotionally.
An ordinary conversation will eventually get stale and both of you will have a hard time relating with each other.
So make sure that you are not stuck on small talk that feels more like a job interview.