My (31F) best friend, S, (31F) have been friends since we were 16. I currently work full-time remote doing digital marketing. She’s married (currently going through a divorce) with a 5-year-old daughter. About a year and a half ago she was tired of her full-time job she had been at for 7 years (it was a terrible company), and her husband convinced her to quit. Since then she’s been back in school for marketing to try and work in my field and hasn’t worked.

Oftentimes we’ll go out to dinner just us and sometimes her daughter. Usually we pay for ourselves, no issues. But I’ve noticed here lately during her divorce, and with her still relying on her husband for money (she’s looking for a job), we’ll go out to eat and she’ll then realize she doesn’t have enough and ask me to help cover part or all of her bill. I’ve done this a couple times but I’m getting tired of it and now lie and say I don’t have enough money to get out of it. She loves to drink and usually orders alcohol which makes her bill even more expensive, while I’m not a big drinker (no judgement to those who are, I’m just not. I joke with my friends that my version of a stiff drink is strawberry milk lol), so I usually order a regular soft drink. When we get Korean bbq, my bill could be $40 with all you can eat bbq and a soft drink, while hers could be $60 or more due to the alcohol, which is another reason I avoid covering part of all of her bill.

A few examples:

1. Me, her and her daughter went to a pizza place. They sell personal pizzas for about $11 each, $14 if you get a drink. I order and pay for my food. She gets a $7 beer and 2 pizzas for her daughter. Her card declines. I offer for her daughter to share with me since my pizza isn’t spicy and S’s is. I didn’t want to, but I wasn’t going to let her daughter not eat (I adore her daughter). She agrees and I share with her daughter. This isn’t the first time I’ve had to share with her daughter because she doesn’t have enough money to pay for them both. I know it’s just food but one of the sucky things about kids is that you always have to share your food with them. That’s one reason why I don’t have any.

2. We got Mexican food. The bill comes. She doesn’t have enough money. Asks me to help. I lied and said I only had enough for me. She has her husband send her money.

3. Most recently, we got Japanese food. She orders a large beer, and I get a pink lemonade. As we’re browsing the menu she checks her bank and says she only has $21 and asks me to help. I have plenty to cover both of us, but I don’t want to so I say I only have $25 for my meal with tip. My first thought is “why didn’t you check your bank account before we came out, or before you ordered a large beer???”. She ends up scrambling and calling her mom to ask for permission to use the card tied to her mom’s account. Her mom gets mad but ultimately agrees.

4. This didn’t directly affect me, but one time me, her and her daughter went out to eat with our friend M (31F). M is a SAHM with a husband who makes a lot of money. This was my first time eating out with her. We were at Chili’s where they have that thing on the table where you pay directly. M sneakily paid the bill. According to S, she does this a lot. I thank M and immediately offer to send her money. She says I don’t need to. S says, “well thanks for paying because I only have $17 so idk how I would’ve paid for me and my daughter ha!”. Mind you, she ordered meals for both of them and 2 large beers.

I’ve decided to ask her upfront if she has money before we go out to eat. While I’m working and she’s not, it’s not ok for her to assume I have extra money to pay for her. She offers to pay me back, but she’s not always the most consistent with it (it took her several months to pay our other friend back $50 for a concert ticket) so I avoid paying for her altogether.

EDIT: I should also add that she only leaves $3 tips wherever we go regardless of the amount. One time at Korean bbq her total was $60 and she left a $3 tip. The older korean waitress actually called her out on it and S said no, it’s enough. She says she usually does this because she can’t afford a larger tip after buying food. This experience was a little uncomfortable. The waitress saw that I left a decent tip and didn’t say anything lol.