It's Like

In the struggle to relate, to describe, something to another person, I constantly use similes. It's like this, like that. Like something you've experienced that might be, even remotely similar to what I'm describing.
The person I'm talking to makes all the difference in deciding what will best relate MY experience. Intrinsically, it's not their experience, and might never be, so it's my duty to communicate it as clearly as I can.
If it's my bartender, who I usually don't know very well, I'll use the least generic universal I can think of.
But if it's someone I know well, I'll say something like, "I imagine it felt similar to when your mother had to cash out her life savings to buy you a car," or, "Pile up everything you've ever experienced in your life -- your relationships, your adrenaline rushes, your darkest moments -- and pour something very flammable on them. Casually light a cigarette with a match, and throw that lit match on that pile. That's what it felt like."

Sometimes I slip up and try to do that to people I don't know very well. I wonder if they understand anyway.