In my experience, siblings usually come up on the first date and I get kind of awkward at about that time. I have a brother I don’t talk to and a brother serving a life sentence, who I do talk to. It’s easy to explain the brother I don’t talk to – he is a certified asshole. Even my mom says so. But I’m pretty anxious that I will have to explain why my other brother is in jail.

He is serving a life sentence with possibility for parole after 20 years for sex crimes of the digital nature. He lived in a heavy handed state with a heavy handed judge. Anyways, he got the book for what he did.

I was in a relationship when the news dropped and my GF was absolutely horrified that I made the choice to even talk to him. I felt that she judged me for his crimes. I said that I agreed that he should be in prison, but that he is still my brother. He had been working through a therapist before the arrest and was fully compliant with the officers hoping for a lighter sentence. While he was a free man, he was an heroin addict for over 10 years in and out of rehab, living in his car or with friends. He was a dead-eyed nobody. Bring sober in prison, he is back to his old self pretty much with a positive outlook on life given his circumstances. He is a cool guy that did some fucked up things. My GF ultimately came around to sympathize with me and admitted that she would probably still talk with her siblings if they were in the same situation.

However.. first date sibling question. That’s a lot of shit to load into someone’s plate.

Choose my adventure:

A) lie and say I don’t talk to either brother, they’re both assholes?

B) Lie and say I don’t talk to him because what he did?

C) Tell the truth, finish the date and hope I don’t get ghosted?

D) Tell her I have two brothers, we don’t really talk, answer vaguely, drop the bomb about a year later?

E) Avoid the question and act like I don’t have brothers?

F) Move out of country and vaguely gesture to the USA any time family comes up?

How would you respond if you were my date and what would you do in my shoes?

4 comments
  1. If you put a gun to my head I would go for D. You’re not lying but you’re also avoiding some possibly vibe killing chat.

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