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Personal finance advice: I've helped pay my friend's bills for years but she can't return the favor - Slate

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Pay Dirt is Slate’s money advice column. Have a question? Send it to Athena and Elizabeth here(It’s anonymous!)

Dear Pay Dirt,

I (cis F) have a close friend of over 20 years “S.” For the majority of those 20 years, I have earned significantly more than S, for many reasons including her bouts of depression and lack of feelings of self-worth that have resulted in her staying the same terrible paying job for many years. For that reason, when we have gone out together, I have always picked up the tab.

I’ve also picked up weekly groceries for her regularly and paid her bills when she told me her cupboards were bare, her kids were hungry, and her phone/power was being cut off. I have kind of resented it sometimes—but then I reminded myself to count my blessings that I am in a position to help.

Well, almost two years ago, I lost my job. I have a new role that I love but my income has been cut by 80 percent and I am now counting pennies every month. My friend knows all this but still seems to expect that the nights out continue on my dime, and I have had to significantly cut our time going out together down as a result. My problem is this. Recently, she messaged me from a tattoo parlor saying how excited she was to get another Ink done. I, then, got pictures of her new hair, her mani-pedi, and her meal out with other friends. Turns out she had a $1,200 bonus (which she then told me she has received every year for the last eight years!) Then yesterday she called up: Shall we go out? I said, no can do, just paid all my bills and I’m broke. I tentatively asked if maybe she could pay for a couple of drinks. She said, “Sorry honey I’m broke! Maybe next week when things are a little better for you?” It took her three days to spend the bonus. So…. the thing is, I’m pissed. Very pissed. I know she can spend her bonus as she wishes—of course, she can—but I’ve picked up the tab for 20 years now. Am I entitled to feel aggrieved about this or do I need to still count those blessings?

—This Gravy Train Is Salty

Dear This Gravy Train Is Salty,

I generally don’t advise people to judge others who may be financially struggling for occasionally spending on things that bring them joy. You rarely know whether someone has saved up for what they’re buying, it’s a special occasion, or it’s just something they rarely do. But even if one of those scenarios applied here, your friend has a lot of chutzpah to suggest that you should still pick up the tab when you’re in similar situations and she just received what amounts to a windfall.

She was never entitled to your help, and it sounds like she’s come to expect it and take it for granted. You need to talk to her about this, or every interaction you have where you have to spend money is going to make you more pissed. I don’t think it will be productive to litigate the specifics of how she’s spent her bonus because you’re correct that it’s her money and you can’t police her spending, but you do have control over the terms of your relationship and under what circumstances she’s effectively spending your money and not her own.

It’s generally easier to have these conversations when you’re not in the heat of the moment, so I’d find a time to talk to her where she’s not asking you to spend money on her behalf or to do something that you know will cost money. Have her over to your place for coffee or something instead.

First, she needs to understand that you are not in a position to continue picking up the check, and going forward, you’ll need to split it when you go out. Remind her politely that you’ve picked up the check for a long time and didn’t mind doing it when you could afford it, but that’s no longer the case. You’re having to cut expenses yourself. Then you have to actually enforce your rule. The next time she wants to go somewhere, ask her ahead of time if she’s able to pay for half. If she says no, tell her you can’t join. Try to suggest activities where neither of you have to spend money.

If this results in her wanting to spend less time with you, unfortunately, that may tell you that a part of what she valued in the friendship was your ability to pick up the check, and you would probably be better off letting the friendship go.

—Elizabeth

More Advice From Slate

I’m a single mother, sole parent to a 6-year-old son. From the time he was 3 months old to 9 months old, I worked 12-hour shifts in a hospital. Since he was just over 1 year old, I’ve worked a regular 9–5 job and I’ve taken him to day care or school in the morning and picked him up every evening and have been home to put him to bed. Next month I will be starting a new job, working 12-hour night shifts in a hospital two hours away from our home. (I’ll commute and will sometimes stay up there without him.) He seems prepared for me not being with him overnight sometimes and not seeing me for a couple days, but he recently asked for a phone of his own so we could exchange messages.

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Personal finance advice: I've helped pay my friend's bills for years but she can't return the favor - Slate
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