H's sister has gotten herself into a mess. the breif version of a long story is that SIL married a guy she dated for about 9 months when she was 21, he's in the military, they immediately moved away and very soon after she got pregnant, she has been a SAHM for the past 3 years, they bought a house, but are behind on their mortgage. They are now going through a very messy divorce (he cheated on her, it's not clear if she cheated on him), she now has a retraining order against him, and she says he is not giving her any money to support herself or their child...big mess. SIL lives on the other side of the country, and only calls when she needs something.
My last interaction with her was a conversation in which I was berated for not spending enough time with FIL and MIL.
She's called H twice this week and asked us to send money (a few hundred dollars, right now). She says she'll pay it back, however I know that if we give her money we should just kiss it goodbye. I'm curious how many of you have lent money to family before? I'm worried that she'll continue asking for money if we do send her some cash or hold it against us if we don't send money. We have lent her money in the past, it was never repaid. She is not good with money (has multiple smart devices with data plans, gets monthly manicures, spends money highlighting her hair, eats out all the time, buys coffee everyday, etc. etc.). I guess it's not really my business to know why she needs the money, but at the same time, if we're giving her money because she's just not smart about what she has are we really helping her. I'm trying not to sound judgemental when H and I are talking about this, but I'm struggling.
Me: 28 H: 30
Married 07/14/2012
TTC #1 January 2015
BFP! 3/27/15 Baby Girl!! EDD:12/7/2015
Re: do you lend (give) money to family?
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
There is one easy answer for this and it's NO
Nobody's ever asked us to borrow money, but I would only give my sister a little bit if she really needed it (I'm talking less than $100 bucks)
We have not given money to family members because it has never come up, but we might if we knew they were responsible and had just fallen on a tough spot.
OP, if I were you, would I give money to your SIL, nope not a chance.
I think that you are looking at it in the right way though. You have to expect that the money is not coming back to you. From an outside view, it sounds like giving her money is enabling her, but I also understand it is his sister and that can complicate things. If your husband wants to give her money, I would agree upon an amount you feel okay giving (not expecting repayment) and then cut her off. If she calls, she doesn't get any more. Or, if you can get him to agree to it, then choose to give her nothing but your emotional support in this tough time.
If she is really struggling I would send her an occasional gift card to help buy groceries and other essentials for her kid. I would also encourage your DH to help her create a budget and offer to act as an accountability partner.
To me it depends on the situation. I would lend my parents money if they needed it and I'd also lend my sister money. For example she saw bed room furniture she wanted on a facebook swap group today, but they're in the process of purchasing a house, so I offered to pay for it and once they settle she can pay me back. I know the banks frown on large purchases, but I also knew she'd pay me back.. and if she didn't I've been looking for a new set
In this situation though I would not lend the money, if she really needed money that bad I think she'd get a job as well. I agree with previous posters that if you send anything send gift cards for food/gas, so you know she can't blow it on unncessary stuff.
I think gas cards is the best compromise, but I'd let her know it's the last time.
She is never going to learn to be responsible for her own finances and personal decisions if she keeps being enabled and bailed out by others.
I'd send her a gas card, and *maybe* a care package of items like TP, diapers/wipes, toothpaste, shampoo, body wash, laundry/dish soap, etc.
Sorry he is still wanting to lend her money. Mine would be the same way and it would definitely cause an arguement in our house.
TTC since 1/13 DX:PCOS 5/13 (long, anovulatory cycles)

Clomid 50mg 9/13 = BFP! EDD 6/7/14 M/C 5w6d Found 11/4/13
1/14 PCOS / Gluten Free Diet to hopefully regulate my system.
Chemical Pregnancy 03/14
Surprise BFP 6/14, Beta #1: 126 Beta #2: 340 Stick baby, stick! EDD 2/17/15
Riley Elaine born 2/16/15
TTC 2.0 6/15
Chemical Pregnancy 9/15
Chemical Pregnancy 6/16
BFP 9/16 EDD 6/3/17
Beta #1: 145 Beta #2: 376 Beta #3: 2,225 Beta #4: 4,548
www.5yearstonever.blogspot.com
So not your problem. Make him take that out of his own fun $