Is 2k too big of a gift for a new friend (<4 months)? I went on vacation with my sons and a new friend and her son for a week. I put the hotel and amusement park tickets on my card for simplicity. After the vacation, she asked me to give her an itemized bill and I got busy with work and life and forgot about it for a month. She now has a lot of big home repairs she has to take care of and it's holiday season so I feel ridiculous asking for 2k from a single mom who makes 10% of what I do. (Cont.)

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That’s very generous of you! Now it really depends on their personality. Some people don’t like to owe money to others like that, esp people they don’t know too well. It could change the dynamic of the friendship as well.

I wouldn’t just forget about it because you also don’t want to let it slide that someone you just met owes you that kind of money and doesn’t say anything about it.

I would just be very explicit about gifting it or saying it’s happy holidays without any expectation of paying it back if that’s true because asking a single mom on a tight budget to “get it next time” may be stressful for her too. I’d just bring it up and gauge reaction and go from there.

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Making new friends is hard and I’m sure you’re fine in judgement of character but I’d also want to make sure friendships are built on the right foundations. But you definitely do you! It’s an interesting situation and I’m interested in hearing what others have to say.

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Be careful that she doesn't think you're trying to buy affection. Also be careful that you're not setting a very dangerous precedent.

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I'm definitely not at risk of the former but will have to be mindful of the latter.

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Give her the itemized bill and let her react to it. She knows how much she intended to spend before going on the vacation and probably set the money aside. If she didn't she wouldn't have asked for the bill

Do NOT get into not sending a bill because she makes less.

Costs are discussed up front and agreed to. Keep it simple.

To some others points around just make it a gift...this is someone you've known 4 months not 4 years. Can set a bad precedent where she expects you to pick up tabs because you better off financially.

If the next time you all go on vacation you can say hey I'd love to get the park tickets as a Xmas gift and if she opts not to go next time due to cost that's okay too or you all can compromise on what activity/ vacation you take

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…what type of new friend is she? If she’ll be around for a while, but wants the itemized bill, I’d share the itemized but not ask her to pay for it. The itemized isn’t a bill. Offer to let her pick up the tab, etc when you hang out next.

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Let it go.

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10% of what you make? I’d say hey, I forgot about this and I know it’s a lot of money with everything you have going on, so let me just cover it this time. Happy holidays!
And then if she’s really uncomfortable with it, she’ll pay you back eventually

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Should I let it go as a gift? Send her a bill after the holidays are over? Send her a bill and say no rush?

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Live and learn.
Next time, split the hotel at checkout.
Let everyone get their own entrance tickets.
Ask server to split meals when you get seated.

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It's not talking about money it's putting her charges in front of her. Not giving her the bill when she asked for it - talks about money much more and can be more uncomfortable

It's not what ya say it's what ya don't say sometimes

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If she asked for the itemized bill, I bet it’s top of mind for her and she would pay you if she could. If it’s not a big deal to you, I would just enjoy the memories and if she brings it up and wants to pay you back in the future - great.

I did something similar one time with a friend (though on a smaller scale) I put a nice dinner on my credit card (we had to buy tickets up front ). I never got a notification that she sent me a Venmo so I was a little annoyed. At dinner she was so grateful that I had spent time with her around her birthday that I assumed she thought I was paying for the whole thing. I decided to let it go because we had a great time and her birthday is a big deal for her (I have known her for 15 years so feel confident describing her this way). When I found her Venmo a week later, I felt like an ass. People surprise you - so don’t count her out.

She may even try to repay you in other ways - so again, if money isn’t an issue for you, enjoy the time you spent.

I travel with a good friend often, and we have our system down. We just pay for everything we can with credit cards and usually one puts the hotel on their card and the other pays for meals and excursions and then after the trip we each share a list of the shared costs we paid for and figure out who owes money based on a 50/50 split of the total. We don’t fuss over things like one person ordering room service or having extra cocktails or whatever. It always works out fine, but we’ve been close friends forever.

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