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Hard to Say is This Recording’s weekly advice column. It will appear every Wednesday until the Earth perishes in a fiery blaze, or until North West turns 40. Get no-nonsense answers to all of your most pressing questions by writing to justhardtosay@gmail.com or by dropping us a note at our tumblr.

Hi,

My boyfriend Davis served a short prison term from 2011-2012. He was incarcerated because of a drunk driving incident where he harmed another driver.

Davis and I have been talking about possibly getting engaged in the next year. My question is whether you think I should mention any of this to my family before or after the engagement/wedding?

Mallie R.

Dear Mallie,

It is impossible to keep such a thing a secret if you are going to include Davis as part of your family. It is going to come out at some point, e.g. when his prison buddies show up to take you hostage demanding liters of your blood or Jim Beam.

The key is to present this information to your family in the correct way. That correct way includes while Davis is performing some relevant community service, like ladling out soup at a kitchen, counseling young individuals on the error of his ways, or cunnilingus. Let your family know that Davis is a changed man. I assume he gives speeches for a modest rate as a part of his rehabilitation? OK, see ya.

Hi, 

After my freshman year of college, I feel like all the people I met there are so much more like me. It is difficult to go back to my high school friends. The subjects they talk about seem rote in comparison, and all they want to do is smoke pot, play video games and gossip about things that frankly do not matter much to me anymore.

Is there any graceful way to get out of this or hang out with them without wanting to tear my hair out?

Karen B.

Dear Karen,

Becoming educated means that everything you once enjoyed will now taste and smell like shit. You will never be able to enjoy your high school friends as you once did. They are lost to you, as is the music of Kelly Clarkson, the thrill of Orange Julius, and anything purchased from Urban Outfitters.

It is on you to uplift your old friends. Take them to see art and music: perhaps a production of It's A Wonderful Life staged by a local regional theater might lead them to realize what silly dodos they are being. They need to love each other, but not at the expense of culture and class. Explain why every painter since 1891 was a total asshole. They will be unable to find out such information on wikipedia; perhaps they do not even know what wikipedia is? You must show them.

Illustrations by Mia Nguyen.

"Song to the Siren" - David Gray (mp3)