building bridges

Just a little while ago, Chicago asked if he could speak with my father. I talk about my family pretty frequently, he's visited the house and whatnot, and he's in search of some personal and professional guidance. As he told me, taking one year off of going to college damn near turned into ten, with not much headway. While at the time, he was making pretty good money from the perspective of an 18-year-old out the gate - since then he's been working a string of customer service-type jobs and currently looking for a more stable situation. He's told me before that he wants to get where my father is in life - a nice house, family, and job - and bypass the model that his own father gave him, which was floating in and out of jail for his entire life.

I can definitely respect the dream here. The truth is... I see a lot of similarities between Chicago and my father. At 26, my daddy was living with grandma, car-less, and working a dead-end job. At the time my parents got married, my daddy was working at a plumbing supply warehouse stocking shelves. From someone who's been somewhere similar, I feel like he can learn a lot from my old man. And I'm entirely humbled that he would even reach out and ask.

The trouble with me is my lower-level anxiety about broaching the subject. The words haven't been spoken aloud, but I know my daddy had aspirations of me getting with one of the doctors or lawyers or Ph.D.s of tomorrow. Well, that hasn't happened. He has met Chicago on a few occasions, but they don't really know know each other. To introduce him to the fam like this just seems, well, huge. Will my dad respect the fact that I deeply care for this man, even if he's not exactly whom he'd always envisioned for me? Will be willing to open up that door? Will Chicago be able to stomach my dad's blunt, to-the-point-ness and really be willing to face some of those not-so-great decisions he's made over the years? How will I feel about opening the door on this type of relationship between the two of them?

Basically, all these questions to myself to say: Are you really ready for this, for real, for real? I feel like it might be time.