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She needs a sitter. Is it wrong of me to pay for them?

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Question - (9 March 2009) 3 Answers - (Newest, 10 March 2009)
A male United States age 51-59, anonymous writes:

I find myself going out with a single mother. Nothing out of the ordinary though it's something I never thought I'd do. She doesn't have any family or close friends so when she's out with me or at work she has to use a babysitter as she has two very young children.

A few times she has said she'd love to get together with me, but isn't able to get anyone to watch her kids or can't afford anyone to watch them. (We have not yet progressed to the point where taking them out with us is an option.) A few times I've been tempted to say 'find a sitter and I'll pay for them.' But I don't know if that is PC. I mean I don't want to imply to her that she's poor and I have to come to the rescue. I also don't know what the manners or custom is regarding that.

Is paying for her kid's babysitter something kosher or is that an area that bluntly is none of my busines right now?

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A female reader, confused0223 United States +, writes (10 March 2009):

That would make her feel wonderful, to know you care that much. Just say "you deserve a nice night out, find the sitter, and I paying!" I would love if a guy did that

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A female reader, jessica04 United States +, writes (10 March 2009):

jessica04 agony auntI think if you called her up and said "I'm taking you out, call the sitter, I'm paying for her as well" she would be floored and flattered. Kids cost money, and it would be really nice for her to see that you don't view them as obstacles.

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A female reader, anonymous, writes (9 March 2009):

What a lovely idea i say make the offer

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