Anonymous wrote:"Enabling" is kind of weird here. When I pay for daycare or $200 that they are short for rent, I don't feel like I'm enabling them. What is the alternative? They lose their house or their childcare (which would cause more problems down the line).

Do you understand that they are not cutting back on extras, and they are not putting themselves in positions to get more work or higher-paying work, because they know they can count on you? THAT is enabling.

Just say that you've taken a look at your finances and decided as of the start of 2019 that you need to rearrange how you manage your money and can't lend/give anymore going forward.

You might be enabling it, but you're Anna's piggy bank.

Trust that your DF will not allow you to keep giving your friend money like this once you are married.
And I agree with everyone above that you shouldn't be giving the money out to begin with.

Stop giving your friend money. It doesn't help the situation and obviously is causing problems. They are going to have grow up and figure out their own financial problems from now on.

As for your BF going off on Mike - I don't blame him even if it was a low blow to Mike. Have him apologize if he hasn't, but don't push it. In my opinion, Mike owes everyone an apology. I don't buy into the concept that he should be allowed to be an ass just because he doesn't have money. This wasn't a one-time situation since it's clearly happened several times before. I also don't buy the fact that he didn't know that you (or someone) gave them money previously. Didn't he wonder how those bills got paid...?

I would personally let Anna know that the money flow is done because it clearly makes Mike uncomfortable. If they need the money then they will need to figure out a way to get it. People do it everyday.

Anonymous wrote:Thanks everyone! Op here.

Anna and I have always been supportive to each other. She helped me when I didn't have things and we are just so close that it feels wrong to not help out but I understand that this is muddying things a bit.

There have been times when I said that we couldn't swing it if she asked for money and she never got mad or upset about it, she understood.

As far as my DF, when Mike went off on us we were both really cool and quiet about it. As I said, I told Mike that we obviously just want to help if we can. He continued arguing and made a few personal remarks/insults which is when my DF told him about the other money. I talked to DF and he said he wasn't trying to "throw it in his face", but he felt angry that Mike (who will be the main one using the car) was being so disrespectful.

I hope this clears things up.

Help Anna by listening, by saying encouraging things, by helping her study for tests that will qualify her for higher paying jobs, by passing along a coupon to a store she frequents that you don't need. I am VERY close to my sisters and my two best friends. We do not lend each other money. Let go of Mike's issues - he was embarrassed and couldn't handle it. Just never bring it up again.

You're treating that 'friend' like she's a second wife or a child. You need to wise up OP. Your fiancee is right and well...the DH of the friend is ungrateful.

Anonymous wrote:"Enabling" is kind of weird here. When I pay for daycare or $200 that they are short for rent, I don't feel like I'm enabling them. What is the alternative? They lose their house or their childcare (which would cause more problems down the line).

Your friend gets another job, your friend makes her DH get a job, they cut their expenses, just to make a few.

Anonymous wrote:"Enabling" is kind of weird here. When I pay for daycare or $200 that they are short for rent, I don't feel like I'm enabling them. What is the alternative? They lose their house or their childcare (which would cause more problems down the line).

Good god. This is the definition of 'enabling'. You are enabling them to avoid getting their financial house in order.

Anonymous wrote:OP again, just to clarify. We have never given the money as a loan, it was always just a gift not expected to be reciprocated. Anna would usually make me a baked good and give me a card but we never expected repayment.

Anyone that asks you for a loan, and you give it as a gift, more than once is using you. The friendship is wayyy unbalanced.

You and your DH need to get on the same financial page. If you're going to give money to 'charity', you need to agree on how much and on what occasions. Mike and Anna, clearly, are not on the same page when it comes to finances. THEY are living beyond their means and their current strategy (you) is unsustainable. Since Mike wasn't aware of other gifts of money, it's clear Anna has already been sneaking/hiding from Mike. If you continue to give her money, you can bet she's not going to tell him. You are only delaying the inevitable financial reckoning they need to have. Stop it.

"Enabling" is kind of weird here. When I pay for daycare or $200 that they are short for rent, I don't feel like I'm enabling them. What is the alternative? They lose their house or their childcare (which would cause more problems down the line).

OP again, just to clarify. We have never given the money as a loan, it was always just a gift not expected to be reciprocated. Anna would usually make me a baked good and give me a card but we never expected repayment.

Anonymous wrote:Thanks everyone! Op here.

Anna and I have always been supportive to each other. She helped me when I didn't have things and we are just so close that it feels wrong to not help out but I understand that this is muddying things a bit.

There have been times when I said that we couldn't swing it if she asked for money and she never got mad or upset about it, she understood.

As far as my DF, when Mike went off on us we were both really cool and quiet about it. As I said, I told Mike that we obviously just want to help if we can. He continued arguing and made a few personal remarks/insults which is when my DF told him about the other money. I talked to DF and he said he wasn't trying to "throw it in his face", but he felt angry that Mike (who will be the main one using the car) was being so disrespectful.

I hope this clears things up.

I stand by my initial reaction that something is off here . . . you shouldn't be enabling your friend.

Thanks everyone! Op here.

Anna and I have always been supportive to each other. She helped me when I didn't have things and we are just so close that it feels wrong to not help out but I understand that this is muddying things a bit.

There have been times when I said that we couldn't swing it if she asked for money and she never got mad or upset about it, she understood.

As far as my DF, when Mike went off on us we were both really cool and quiet about it. As I said, I told Mike that we obviously just want to help if we can. He continued arguing and made a few personal remarks/insults which is when my DF told him about the other money. I talked to DF and he said he wasn't trying to "throw it in his face", but he felt angry that Mike (who will be the main one using the car) was being so disrespectful.

I hope this clears things up.

That level of financial help between friends is neither normal or healthy. Something is very off in your situation, and clearly Mike resents it.