How do I gently remind my friend to pay me back?
July 11, 2021 8:35 PM   Subscribe

I have a friend who regularly lets me pay for him when we're out together and rarely pays me back or returns the favor. How do I politely ask him to pay me back or somehow let him know I'm not happy with this without unnecessary awkwardness? I value this friend very much and don't want to make him feel bad.

I often end up paying for my friend - let's say we're out for drinks and we also order some snacks throughout the evening. If I'm the first to pay at the end of the night, I pay for my drinks and the snacks we shared and I don't think twice about it, but I would expect my friend to somehow acknowledge this and maybe pay for snacks some other time. But this never happens - he either doesn't seem to notice I paid for him too or he might remember the next day and say he'll pay next time and then he never does. The same scenario often happens if I end up paying for his drinks (e.g. if they don't accept cards and my friend doesn't have cash), cab rides, entrance fees, take-out meals etc.

I never asked him to pay me back because I don't wanna be that person who keeps track of these things, and I honestly wouldn't mind at all if there was some kind of reciprocity, but there isn't really. I don't think he does this on purpose, but it's happened so many times now that it's becoming a pattern and if I could somehow count all the things I ever paid for him, it would add up to quite a lot of money by now. I would rather use this money to pay for my partner's drinks for example. I also have a new mortgage now so I would prefer to cut down on unnecessary expenses.

Obviously, I value this friendship much more than the money, and I wish I was rich enough to pay for my friends without having to worry about it, but unfortunately that's not the case. In fact, we both work in the same field in similar positions, so I think we earn roughly the same - if anything, my friend probably earns more than me.

I think part of the problem is that I always remember when someone pays for me and I make sure to pay them back or pay for them next time, so this is what I would expect from other people as well, and I guess not everyone works like this.

How would you approach this?
posted by U.N.Owen to Human Relations (34 answers total) 4 users marked this as a favorite
Your friend is being, "that friend," which is okay, until it isn't.

"I also have a new mortgage now so I would prefer to cut down on unnecessary expenses." This is nice phrasing.

If you'd like to be more covert, "Hey, that friend, I am prioritizing/focusing on paying my mortgage. Would you like to make drinks at your/my place? Or perhaps would you be into grabbing rounds for a bit, while I catch up on my mortgage?"

This person may do it frequently with others: it doesn't necessarily mean they're a bad or use'y friend, they may have found ways to socialize and feel they contribute to the relationship in other ways. They may just get by and believe you understand more deeply than you'd like or actually do.

Don't be afraid to be forward, you've been really cool about this and it just shouldn't be a problem. Hopefully your friend will simply return the energy, right away.

source: Person who was occasionally that friend, not out of ill-intent, but enough fortune to have friends in varying degrees of flexibility. Was very happy to return the efforts, later, with and without prompting.
posted by firstdaffodils at 8:43 PM on July 11, 2021 [4 favorites]

I'm not sure how you could ask for 'back payment' on past hangouts without being it awkward, but going forward, I would say 'Hey, I got the drinks/food/cab last time, can you get it this time?' or some variation on that every other time you see each other.

Or when planning time together and meeting up at a bar/restaurant comes up, you could say 'I'd love to, but I'm trying to cut back on going-out costs, maybe we could hang out at mine?' and see if they offer to still go out and cover your way, or simply hang out more low-key and in a less costly way, saving you both money.
posted by rachaelfaith at 8:46 PM on July 11, 2021 [26 favorites]

Well, you're already that person who keeps track of things (broadly if not precisely), but there's nothing wrong with that. Everyone wants to feel like their contributions are valued, and are paid back at least in some holistic sense.

I would try introducing some gentle suggestions about who should pay for things when you guys are out together. Like, "Do you want to buy us some snacks?" "I think it's your turn to get the fries." "Here's twenty bucks but I would like to drink that cab ride next weekend." Idk. If your friend takes the hints, that's great. If stuff like this leads to conflict, then the problem runs deeper and you'll have to figure out what's going on and what you want to do.

I don't think you're gonna be able to ask for an accounting of all the excess snacks you've bought so far, and try to get paid back for it. Or, anyway, I think that would be a much trickier problem to approach. But, looking forward, I think a reasonable initial response to your friend not automatically doing what you want would be to explicitly ask for what you want, on a case-by-case basis.
posted by grobstein at 8:48 PM on July 11, 2021 [8 favorites]

In the future, do not offer to pay for him.
posted by saturdaymornings at 8:48 PM on July 11, 2021 [87 favorites]

I can sympathize.

What has helped me is to vocalize an easy solution. “I’ll get our Uber ride and you can get the first round of drinks”, “I’ll get the movie tickets and you can get dinner”, etc. See how your friend reacts. Any reasonable human will be fine with this. If they aren’t? They suck.
posted by Diskeater at 8:52 PM on July 11, 2021 [22 favorites]

He's not asking you to pay, right? I mean, you're proactively picking up the check (in many cases) on your own initiative?

Could you just stop paying for him? When it's time to settle up just do the math and tell him what his share is, or say "Split it down the middle seem fair?"

If you're making plans to hang out remind him to get some cash on his way to wherever you're meeting up. It doesn't have to be weird, just... do it.
posted by under_petticoat_rule at 9:00 PM on July 11, 2021 [50 favorites]

As someone with a bad memory, I’m always afraid of being “that friend”. grobstein’s phrasing is good and would work for me if I ever accidentally got too unbalanced with a friend of mine.
posted by mekily at 9:04 PM on July 11, 2021 [2 favorites]

Scope out and go to casual venues where you each order and pay separately up front. Or hang out at home.Hopefully he enjoys your friendship without the entertainment subsidies.
posted by dum spiro spero at 9:05 PM on July 11, 2021 [1 favorite]

A friend and I have naturally picked up a pattern of reciprocity. We meet for drinks, one of us pays, we then go to dinner, usually the other one pays but sometimes we split, and if we go for more drinks after dinner, whoever's "turn" it is gets it. And it sounds like something along those lines would work for you as well.

In your case if you want to address it in the moment, after you already paid for something, then the next time an expense comes up that would be normal to reciprocate, maybe just say "Are you paying for this one?" and then do nothing. Don't bail your friend out by paying for it, unless the bartender/whomever is waiting for a payment. Try to time it for when you're walking into the next place, or talking about where to go next, not when you have already ordered if you can. If you have to bail out your friend, just ask why. If that happens, your friend needs to own up to flat-out not paying when asked to. It's possible he only does it once and then stops. If that's the case, you'll need a conversation about the pattern.

If either your friend doesn't get it from the not-so-subtle hint, maybe ending the night instead, or doesn't change his pattern, then you would need to have a more pointed conversation. At that point, just lay it out there. You need to be more careful with your spending, you feel the spending should be more balanced, etc. And then stop and let him respond. Maybe there's a reason that he can give. I'm not saying it's a good reason, or a reason that erases the need for him to pay his part, but perhaps a reason he feels is valid.

Being clear that you need him to pay some of it is important so there is no doubt, no chance of him misunderstanding. Could this cost the friendship? Possibly, though he would need to be a terrible person for that to happen. Any change to a friendship risks losing it.
posted by Meldanthral at 9:10 PM on July 11, 2021

I think this depends a little on whether you think he's subconsciously freeriding or just forgetful. If it's the latter, why not say, "hey I'll pay for the snacks and Venmo you for your half later" or similar. In other words, if he's bad at keeping track, and you're doing it anyways, just take care of that bookkeeping and make it easy on him. If he's not taking advantage of you, it shouldn't be a big deal. You can even say at the beginning of the night "hey, why don't I pay tonight and you can Venmo me so we don't have to keep asking for split checks" and make it seem like a convenience thing
posted by matildatakesovertheworld at 9:17 PM on July 11, 2021 [8 favorites]

Yeah, "the kids these days" Venmo and when I didn't have Venmo set up, people were all "never paying you back, then." You may have to pressure him to Venmo you right away while he's still there with you.
posted by jenfullmoon at 9:27 PM on July 11, 2021 [4 favorites]

Venmo is US only - so may not be an option...
posted by birdsquared at 9:36 PM on July 11, 2021

(For a fun time, read this thread through the ask culture vs guess culture lens)

Hints will do absolutely nothing to change this dynamic. You either need to lean into the awkwardness or lean out.

Leaning out means avoiding the issue as much as possible. Only spend time together when it won’t cost any money. Only go to places where you can afford to pay more than your share. Be vocal about cutting back on spending.

Leaning into the awkwardness means having a very direct conversation, best done when you’re on your way out for a round of drinks or something—do it as a precursor to a fun evening together, not when you’re about to part ways. Think of it as the critical middle of a compliment sandwich. You want to convey “this is on my mind, but it’s not so upsetting I can’t have a good time with you.

The goal of the uncomfortable conversation is to collectively come to an understanding of expected behavior, perhaps him giving you explicit permission to speak up about it being his turn to pay.

Steps for the awkward conversation:
1) ask for his consent to have an awkward conversation. While it’s perfectly legit to start a blunt conversation without him agreeing to it, this is a move that sets you up to have a chat that’s *mutual problem solving* instead of just you making unilateral decisions about how your friendship works.

2) lay out that you feel like you end up paying for more than your share of refreshment and entertainment when the two of you are hanging out.

3) as much as possible, explain this as a feeling about a pattern. Rather than compensation for specific events in the past, bring this up as *avoiding* *feeling* that things are unbalanced in the future. Even if he tries to “settle up” for the past, you can say something like “I don’t want to hold your forgetfulness against you for the times you didn’t know it was stressful for me. I’d rather focus our energy on making it less stressful for me in the future.”

4) abandon the idea that your friend will ever intuit that he should pick up the slack (maybe he will over time, but you’re better off assuming that informal IOUs are just not sticky in his brain, and this won’t change unless it’s causing *him* discomfort).

5) Work with him to find call-out language or an IOU system that you’re both willing to abide by. Maybe this is just getting lots of reassurance from him that it’s ok for you to flat out ask him to pay for things sometimes. (If this gives you a venue for speaking up and asking for things to be fair/equitable, bonus!)

6) throw in a mention about “I enjoy being generous with my friends, but I prefer it to be when I’m intending to be generous, not because they forget to pay me back”

7) seal the conversation with something like “thank you for listening, this topic is important to me” and make a brief mention about how you deal with feelings of inequality wrt financial contributions in the future.

Tldr, try to spin it as both of you vs the problem, not you vs him
posted by itesser at 10:15 PM on July 11, 2021 [11 favorites]

In the UK we have the concept of rounds of drinks. You alternate rounds with everyone in the group. If you happen to be the one at the end of the night who hasn't bought a round, your friends will actively remind you it's your round first the next time you go out. If you manage to dodge paying more than twice running, they will actively remind you for ever more, which gives you every incentive not to do that.

Next time you go out, you say at the start of the evening that it's their turn to pay because they haven't paid in some time. You make sure they pay. You keep doing that every time you go out, until you feel satisfied with the result, or the topic of who pays comes up naturally and you have the talk you should clearly be having.
posted by How much is that froggie in the window at 10:52 PM on July 11, 2021 [5 favorites]

I have a friend who regularly lets me pay for him... If I'm the first to pay at the end of the night, I pay for my drinks and the snacks we shared and I don't think twice about it, but I would expect my friend to somehow acknowledge this and maybe pay for snacks some other time

It sounds like your friend isn't "letting" you pay so much as you are snatching up the check and paying for the whole thing without even consulting them.

Generally when I go out with friends we either have separate checks, or if everything is combined when the bill comes we make some noises about who got what, and everyone starts throwing cash on the table until we have covered the bill plus a nice tip. Once in a great while one person will sneak off and cover the entire bill SPECIFICALLY as a gift. (of course giving gifts and doing favors for friends is it's own kind of trading off of things) Trading off who pays the bill is more of a thing for romantic partners to do than for friends.

I guess another exception to this is that sometimes I just want a friend to go with me who doesn't feel they can afford to go out, in that case I will be very clear with them about what I am paying for and offer some sort of reason behind why I am treating them, so they don't feel obligated to pay me back.

Personally I would be kind of ticked off at a friend if they grabbed the whole bill and paid it, but instead of a gift they had strings attached and expected it to be some sort of accounting thing that I had to keep track of -- why make things so complicated when we could just get separate checks???

Of course there are different customs everywhere, but it's entirely possible that your friend doesn't follow this trading off sort of thing. It's very awkward to understand how it works if one isn't used to it! I'm assuming that this isn't a friend you have known for a long time, if you are having a mismatch on how friends deal with restaurant bills -- you might just not be following the same set of unwritten cultural assumptions.

It sounds like part of the issue is that your friend often doesn't have cash, or perhaps doesn't have the funds available on other forms of payment? Maybe you need to do things that are less expensive, or go to places that take cards. And maybe change some things about some of your plans -- I'm not sure how you are ending up in a situation where you are paying for their cab rides and takeout!
posted by yohko at 1:07 AM on July 12, 2021 [12 favorites]

I think going forward, you don't remind them to pay you back, you encourage them to pick up their fair share.
posted by DarlingBri at 1:25 AM on July 12, 2021 [7 favorites]

I would (and have, from both sides of this situation) say to the friend that from now on I’d like if we could immediately either square up (e.g. paying over venmo or splitting the check) or make a record/IOU of the transaction (e.g. requesting money over venmo, putting the cost into splitwise, or a non-app running list of how much is owed).

Depending on how close you are with this friend, I also don’t think it’s out of the question to bring up the possibility of back payment. If I were you, I’d probably say something like “It feels like we’ve been getting out of balance with respect to paying for stuff, and I’d love for things to be more equal. Since I spotted you the past x times, how would you feel about spotting me the next x times and then we can switch to more frequently settling up?”
posted by chaiyai at 2:20 AM on July 12, 2021

I would just have a conversation that went something like this: "Hey friend, I just realized I've been picking up the tab for us pretty often without even thinking about it or discussing it with you. Now I have a new mortgage, and I need us to split the check whenever we go out together. Can you help me remember to do that?"

One of my friends consistently picks up the tab whenever we have lunch, a couple times a year, because it is understood that he is fully employed in a high-paying job and I am… very much not. Every so often we will go out for coffee, and I will pick up the tab. If it turned out that he was resentful or unhappy with the situation, I would be completely horrified. Thus far there's been no indication that that's the case. When I've offered to pay, he has refused.

It's entirely possible that your buddy believes that you are being generous on purpose and doesn't realize you're waiting for them to pull their own weight. So you just need to clear that up. Also, this doesn't have to be awkward. It can be awkward if it feels awkward to talk about money. But really, it's a conversation about your relationship and how something that maybe appeared to your friend to be working is not actually working and needs to change.

If this person is a good friend, they will respond appropriately and support the change. If they don't, then you have important information and can proceed accordingly. Good luck!
posted by Bella Donna at 2:21 AM on July 12, 2021 [15 favorites]

One of my friends consistently picks up the tab whenever we have lunch, a couple times a year, because it is understood that he is fully employed in a high-paying job and I am… very much not. Every so often we will go out for coffee, and I will pick up the tab. If it turned out that he was resentful or unhappy with the situation, I would be completely horrified. Thus far there's been no indication that that's the case. When I've offered to pay, he has refused.

This is also true for some of my friendships. But normally, these people will reciprocate in some way, doing something nice or pay for something sometimes. They also every now and then offer to pay, to check that this approach still works for me. And your friend isn't doing these two crucial things.

Clearly, it would be nice to reset expectations. But also, stop enabling this behaviour pattern. Stop just picking up the tab or just paying for the snacks. When they want to do things that require them to pay by cash and they don't happen to have any on them they can go and get cash, even if planning ahead or finding an ATM at the time is less convenient than you giving them cash. That's just adulting. Due to the pandemic you have greatly reduced your own use of cash and you now rarely have cash on you.

If they start to pay their share that's great. If they start to suggest lower cost activities as a result that's great. If they start to get weird about making plans with you, you learn very useful information about your friend.
posted by koahiatamadl at 2:46 AM on July 12, 2021 [2 favorites]

If you've neve overtly discussed it, your friend probably has no idea this dynamic even bothers you. Agree with the great "lean in or lean out" comment above, and choose your direction. Hopefully a workable future state will emerge and you can move forward.
posted by I_Love_Bananas at 3:29 AM on July 12, 2021 [1 favorite]

I would opt for this first if you want to avoid an awkward conversation:

The waiter hands you the bill. Without missing a beat, take out your calculator and split it. "Okay so that's £25.40 each". Or as soon as the waiter comes over at the end - "can we have separate bills please?"

If you always jump in to pay then it should be easy to jump in and set the payment strategy.

If this doesn't work and he does the "I'll pay you back" thing then I would go for rachaelfaith's suggestion above and mention that you're cutting back on going out costs. I would probably labour the point and add "it's too expensive paying for two".

When you set boundaries it is always going to feel awkward for both people but I think these are the least awkward methods.
posted by ihaveyourfoot at 4:07 AM on July 12, 2021 [1 favorite]

If you are 1. proactively picking up the entire tab and 2. never asking for money, there is every chance your friend thinks you are doing it as a gift because you make more money than they do (whether or not this is actually true), and they may feel the fact that you never mention it means that they shouldn’t either because that would make it weird.

You really shouldn’t ever go “I have provided an unasked-for favor and I have never acknowledged the fact that I am doing so, but the fact that other people also aren’t acknowledging it makes them dicks.” You have no idea what the friend thinks is happening here, because you never asked, you just assumed.
posted by showbiz_liz at 4:43 AM on July 12, 2021 [26 favorites]

Sad to say, chance of your friend starting paying his share is "slim to none". He's gotten used to mooch off of you. And you keep enabling him.

So what's your end goal?

a) He starts paying his share, but no discussion of "owed" -- possible if you start insisting on split checks this day forward.

b) He pays the past shares AND future share -- not gonna happen. He's used to mooching.

c) He does nothing, status quo -- up to you, if you want to keep enabling him

d) Cut ties and cut losses -- better on your wallet, worse on your "friendship" (yes, I put that in quotes)
posted by kschang at 6:12 AM on July 12, 2021

Start paying for things with him in cash. This actually solves the problem really elegantly. If you have the right cash your your stuff plus tip, there's no reason to cover for each other.

Waiter brings $24.50 check. You put down $15. No reason to trade off or do anything different.

If your friend asks, "I'm just spending through some cash I have"
posted by bbqturtle at 6:51 AM on July 12, 2021 [2 favorites]

I have deliberately been The One Who Pays when I know I'm way better off financially at the moment, but still want to take a friend to nice places. (I know this isn't you, but it seems like maybe your friend thinks it is.)

If I wanted to stop, I would say "oh and let's plan to go Dutch this time? I really have to watch my pennies right now" during the planning phase. Then yes to either bringing cash or asking the waiter for separate checks. Don't loan the money or cover him, it just ain't gonna happen.

I agree that you probably are out of luck on past items, unless you're willing to take a hit to the friendship over it
posted by february at 7:22 AM on July 12, 2021 [7 favorites]

Next time you're at a cash-only place, YOU are the one who doesn't have cash on you.

Next time you're paying your tab, only pay for your drinks and not your shared snacks.

posted by DoubleLune at 7:36 AM on July 12, 2021

- Your friend is almost certainly aware of the imbalance of payments between you two. He may be allowing this to persist because he is cheap, broke, or shameless.
- The money you've already spent is gone. File that under "educational expenses."
- The next time you two are out, don't reach for the bill. If he's letting it sit on the table like a dead rat, say "I'm going to let you pick this up." No further explanation about having a mortgage or whatever needed. See how that goes. He may tell you can't. He may be reluctant. It may become an opening for a bigger conversation.
posted by adamrice at 8:25 AM on July 12, 2021 [2 favorites]

One more suggestion for the un-splittable items - a friend and I used to keep a "my turn/your turn" card in one of our wallets, and flip it upside down every time one of us paid for the other. Doesn't get you to exactly even, but levels out in the end.
posted by february at 9:09 AM on July 12, 2021 [1 favorite]

If I'm the first to pay at the end of the night, I pay for my drinks and the snacks we shared and I don't think twice about it, but I would expect my friend to somehow acknowledge this and maybe pay for snacks some other time

Mitch Hedburg has a joke that says something like "when someone offers to pay for my drinks, I'll pull out my wallet because I have a card inside that says 'say thank you'. " Not all people need to feel like the rich guy grabbing the check and paying for everyone. You should pay your share and tell your friend to cover his own if it's important to you.
posted by The_Vegetables at 9:40 AM on July 12, 2021 [1 favorite]

I am you. I have a "friend" (actually the husband of my real friend) who does the same. It became a big problem. Here is what helped. I trained myself to say "This will be separate checks." the moment we were approached by a server/bartender. That little phrase was a godsend, there's no arguing it. That way there has to be discussion up front, if there are going to be shared snacks, who is on the hook for paying for them. Its entirely possible that this "friend" of yours is counting on you being too uncomfortable to ask them to pay for their fair share. There are plenty of people who know they are taking advantage of a good natured friend, and don't care. Don't let this happen. Take control right away. "This will be separate checks." You'll feel so much better! Good luck!
posted by WalkerWestridge at 10:50 AM on July 12, 2021 [6 favorites]

I think there's a bit of ask vs. guess culture wrapped up here; you keep track of this stuff, you expect him to do the same and feel put upon when he doesn't reciprocate, while he may not even realize that there's a problem and just thinks of you as an especially generous friend. I suspect that a big part of the solution here is to more explicitly verbalize your expectations instead of automatically picking up the tab and assuming he'll do the same at some point. The best time to do this is before doing a thing that costs money so that he isn't caught flat-footed by the request or has an excuse for making you pay again (e.g. "oh, I left my wallet at home," or whatever).

Do not try to collect "back payments" unless you want your friendship to end on bad terms.
posted by Aleyn at 2:10 PM on July 12, 2021 [2 favorites]

This is the exact reason why I love the Venmo Request feature.
posted by blueberrypuffin at 3:43 PM on July 12, 2021 [1 favorite]

"Here you go, server, put half on this card." If you don't use Venmo or PayPal, you probably can't fix the past issues, but this is how I avoid this. (Or, even better, "You okay with splitting this down the middle, friend?")
posted by nosila at 10:46 AM on July 13, 2021

You know this happens a lot when people ask this type of question. There's an implication that the OP, by noticing that they are always the one paying for somebody else, is really the one responsible for the misunderstanding. Maybe its because they are "too quick to pay." Further, it's often implied that by noticing how often they are paying someone else's way, they are somehow "keeping track" or "keeping score" and that it is ungenerous of them to do that. I for one think that's a bunch of hooey. OP clearly states that this particular "friend" has never once picked up the tab or ever mentioned wanting to do so. That's not ask/guess that's someone who's enjoying the free ride that they know full well they are taking. Anyone who is comfortable letting someone else pay for them constantly is deeply suspect in my opinion. Newsflash, even generous people like to be thanked and acknowledged occasionally. They also appreciate when people don't take it for granted that they are automatically going to pay for everything all the time. Good friends will be adults and make sure to pay their fair share. Not necessarily every single time you go out, but over all you will not be left with the greasy, creepy feeling of being taken advantage of. OP you've noticed there's something amiss. There is a problem, and it's not you.
posted by WalkerWestridge at 3:14 PM on July 13, 2021 [3 favorites]

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