Why do I keep trying?

Every time I win he just comes up with something new and I lose even worse than before.

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Who is he in this scenario?

Roommate.
He can be a nice guy but he’s been acting like an impossible as*hole.

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Sorry @77nick77 . I had a bad roommate before. It’s so hard to deal with, especially when it’s a close friend.

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Yeah I’m debating whether I should have roommates living with me in the future.
It’s not easy.

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Living with room mates can be tough, at times even unbearable. I like living alone. Don’t let your room mate get to you though.

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Do you hang out with your roomy ever? I had a roommate once and we’d stay up all night and watch movies. It was the only socializing I got so I forgave his calling the police on me repeatedly. Lol, he was a whimp, I wasn’t even yelling at him. You just don’t need to call the police on someone for a five seconds outburst.

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