Dear Penny: my friend is dating an abusive guy that looks just like her dad. How do I help?
Dear Penny

Dear Penny: my friend is dating an abusive guy that looks just like her dad. How do I help?

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Dear Penny, I’d like some advice on how to help a close friend of mine who may be in a dangerous situation. So my […]

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Dear Penny: Should I stay friends with the married guy who tried to sleep with me?
Dear Penny

Dear Penny: Should I stay friends with the married guy who tried to sleep with me?

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Dear Penny, Recently I got propositioned by a friend of mine who is married (and not one of those open marriage situations). […]

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Dear Penny: how do I tell my roommate that her happiness is making me depressed?
Dear Penny

Dear Penny: how do I tell my roommate that her happiness is making me depressed?

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Dear Penny, My roommate is self-actualizing in a big way. She had an epiphany about wanting to travel across America and is […]

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Dear Penny: I don’t know this person’s sexual preference; how do I know if this is a date?
Dear Penny

Dear Penny: I don’t know this person’s sexual preference; how do I know if this is a date?

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Dear Penny, I’m a 23 year old woman who is curious about dating other women. I just met this awesome girl at […]

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Dear Penny: Can I ditch my potential roommate if I found a cheaper solo room elsewhere?
Dear Penny

Dear Penny: Can I ditch my potential roommate if I found a cheaper solo room elsewhere?

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Dear Penny, I’ve agreed to move into a place with my current roommate at the end of the month. We haven’t found […]

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Dear Penny: My unfunny friend keeps trying to be a comedian. What should I do?
Dear Penny

Dear Penny: My unfunny friend keeps trying to be a comedian. What should I do?

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Our advice columnist Dear Penny has come back from a long sojourn in the suburbs! Find out how to submit your questions […]

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We’re bringing back our advice columnist, Dear Penny!
Dear Penny

We’re bringing back our advice columnist, Dear Penny!

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Once upon a Brokelyn many years ago, Dear Penny, an advice column dedicated to tackling readers’ recession-related inquiries, graced our virtual pages until […]

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