Susbsidising friend's wine habit

[Tootsurly]

I have a friend who I go out with quite a lot as we're both single and live quite close to each other. When we have meals out he wants to take turns paying which is fine in principle, but in practice he will have three alcoholic drinks and a coffee whereas I will often just have tap water, so his drinks end up costing as much as or more than my food.

I've brought it up a couple of times already, but it feels awkward to broach the subject again, and I can't exactly tell him he's not allowed to order wine with his meal as if he's a child.

He has considerably more disposable income than I do so while I like to eat out I will find deals, or order from the set menu. But there's no point me finding an offer where we can eat for a fiver (Pizza Express After-School Club, in case anyone's wondering) if he then blows £25 on booze and coffee.

I should say, in fairness, that he is not at all tight - he's very generous - and I like his company, but I just can't match his spending power.

Any advice?

(addendum)
@Tootsurly he's actually being a prick. I'm not sure I could be bothered going out with him if he doesn't 'get it'

Start when it’s his turn to pay.
Say ‘given our different drinks etc on the bill let’s just pay for our own from now on’

It must be very obvious to him that his meal is far more expensive. I'm trying to work out what's going on. Are you both men?

He's a CF, say you're each going to pay for what you've ordered each time and after a couple times he might get the hint.

When I go out with friends who drink we split the food bill and they pay for their own drinks. As you say their drinks portion almost equates to their food spend. I'd suggest this or asking the wait staff for separate bills. You say your friend is generous but there's no way he isn't aware.

I like this wording a lot - thanks.

Before ordering say "let's just pay for what we each eat and drink from now on"..

Now that's a great idea!

No, I'm F, he's M. He's also a lot older, in case it's relevant.

Sounds like a dick, frankly. Next time say upfront “Hey Maurice, I’ve said recently to you that I can’t afford to continue paying half your drinks bill. Starting now, we’ll each get our own bill, ok.”

If he’s asked to make your friendship a with-benefits affair and you have said no, perhaps he’s trying to get a different sort of benefit from you. The behaviour continuing after you’ve been quite blunt suggests it is deliberate.

But this wording doesn't help you financially, as you'll still be alternating and paying for all of his wine, just less frequently.

I'd just say "John, I'm struggling with alternating paying and will just pay for my own from now on."

No please, as that implies you're asking permission. It's making it clear that the current situation is a struggle for you and that you will be paying for your own only.

Why don't you take cash to cover your bill and then hand him the total bill and your cash and tell him to pay?

TBH I wouldn't think much of a friend who did this to me.

I've noticed that. But maybe it's because if they're well off, they just don't think it's a big deal? Like I wouldn't mind if their bill was a few quid more, but someone else might say that means I'm well off compared to them, because for some people, a few quid can be a big deal.
But I used to go out with some friends who would always order way more (one couple in the group) and said it was bad etiquette to not split equally. Personally I thought it was ruder to effectively leech.

I can't bear grifters, and he's a grifter. I'm happy to pay for a friend or split, very relaxed about it, but someone who repeatedly orders food and drinks that are twice as much and doesn't pay their way is a grifter and they know it. Grifters never like being called out and never admit it. They always try and make it uncomfortable for the person they are taking advantage of.

Is this man called John or Tom?! So this much older man tries to talk you into a relationship repeatedly, and you pay for his wine? He is a grifter and a sleaze, step away.

But why would she even want to subsidise his drinking every other month?

This bloke is not as nice as he’s convinced you he is, OP. If you want to continue going out with him, then next time calculate what you’ve ordered and your tip, pay yours first. If he objects, he’s an entitled arse, full stop.

Next time you are due to go out whoever does the inviting just text to say “hey, we are going to have to split the bills, I can’t afford to pay for extra drinks at the moment! Looking forward to seeing you/catching up”.
then you just have to be firm either when you order or when you pay that it’s seperate. I would make it easy on myself and come prepared with £25-35 cash, and then you can say either “here is my portion” or “oh I’ve got cash for my half” as needed

And it doesn’t have to be anything to do with a tight budget or ‘struggling this month’. It’s to do with not wanting to be taken the piss out of on an ongoing basis!

Just tell him that things are tight so you need separate bills.

What on earth for? Why is it her job by default to pay for his booze, or to find an excuse if she won't?

She doesn't not pay for his booze because 'things are tight'; she doesn't pay because he's the one ordering it for him! It's not some kind of esoteric wisdom for adults to understand that they pay for what they want to order.

Not that it makes it any better, but he's been coming on to her as well and hoping to woo her into a romantic relationship - which makes him routinely tapping her for several notes to pay for his booze, as per his believed entitlement, even more astonishing!!

Clearly you need to remind him each time that you’re paying your own bill. Maybe when you’ve done it a few times he will get the hang of it.

Tell him that you don’t want to pay for his alcohol…easy

Just say you'll be paying for what you have. He can't argue with that. Nobody could without genuinely looking like they're intentionally rinsing you as a meal ticket.

It's preposterous for someone to split the bill with a tap water drinker when they've had several alcoholic drinks. Unless the teetotaller a big enough eater to even it out.

I wonder if, as well as expecting the subsidies, he might also have a problem with booze (if he's said that he'll go easy on it, and hasn't)... and he kids himself that, if they're both splitting the costs of 'their' meal together, it means that the meal - and the drinks - were kind of for both of them overall.

Exactly. This is wet lettuce-ry of the first order, OP. Just tell him what you’re going to do in future. He doesn’t have you at gunpoint.

There Is no way that he doesn’t know that you are subsidising him. Of course he wants to split the bill. It is cheaper for him.
Just tell him in in the future you will just pay for your own food and drink. It he doesn’t agree then don’t go out with him again.