Who pays for holiday/holiday expenses? Is this fair or just stingy?

[KThughes]

NC/NA for this.

I’ve been dating a man for the past year (15 months to be exact). We both work full time jobs. We do not live together. I’ve never been married and don’t have children. He is divorced with 2 children.

He has always been wealthy. Earns over £2m+ per year. I have always been financially sound/worked. We take it in turns to pay for things and that works just fine for me. I have a good career, but obviously don’t make as much as he does. I pay for all my own bills myself and have never needed financial help from anyone, even my parents.

Since we started dating, he has acknowledged many times that he loves how independent I am as his previous partners were apparently ‘gold-diggers’. He repeats this sentiment often, but even if he didn’t, I love being independent and having my own income and career path. I have no debt and live alone - and within my means.

He’s since sold his company (which was after we met) and has become even more wealthy. Sunday Times Rich List wealthy. Not the top of such a list, but definitely on there.

He now wants to go on holiday to celebrate. As in a blowout celebration. I suggested somewhere more low key and not so crazy. He suggested St Bart’s etc…

He said he’d pay for my flight and we could ‘figure out the rest while we were there’.

I said no, as I am financially astute and would need to know what other expenses could amount to prior. Are we talking additional charges of £1k...? £5k…? £10k...? More?!

I also said I didn’t feel comfortable with this all. He told me to ‘relax’.

He acknowledged that I have a great career and job… but that doesn’t mean I should have to potentially put things on my credit card or dip into savings - for a destination that I didn’t choose. A destination that is astronomically expensive.

I’d happily pay my own way - even my own damn flight if the trip was less extravagant on the whole. I don’t even WANT my flight paid for, especially if it means I’m going to end up being ‘liable’ for many more charges as a result of this trip.

I also don’t want to be called a ‘gold digger’ by him. I can’t help but feel like this is almost a ‘test’ of sorts. It is a really bizarre situation and makes me feel… honestly… gross.

Mean with money, mean with love.
He has known you a year. Knows your character. Yet he's still trying to test you?
Mutually agreed budget, or he covers the deficit.
What a CF to dictate that you spend £££ on a holiday to celebrate HIM coming into money. It's not even his birthday or anything. It's like me winning the lottery and then asking everyone else to pay full price to come on holiday to celebrate MY newfound riches, none of which is heading their way!

Part of being a financially astute and independent person is recognizing what you can and can’t afford and being savvy abouts committing to expenses. You are doing all of this, don’t let him shake you or railroad you into going against your better judgment.
I agree with the pp about it being somewhat gaslighty, almost trying to goad you into proving yourself. I’m not sure I like the sound of him.

Not sure if I'd believe his £2m a year salary. I would decline his offer and not go.

This would give me the serious ick OP. Can't beqlar stinginess from someone who clearly has money.
I am as independent as they come but would not get into debt to celebrate some else's wealth.

I’d go with “Look, I’m not committing to a holiday when it’s not clear how much it’s going to cost me. I’ve worked out I can afford to pay £X to go to St Bart’s which has to cover all my expenses. If you anticipate me needing to spend more than that then I’ll have to decline or we can find another holiday that suits both our budgets, just let me know which”.

Oh great! We’re going to celebrate your fabulous success and wealth with a holiday I can’t afford !

You know, he didn’t get rich by committing to unknown expenses or letting other people push the agenda. If he wanted a flash holiday and your company, he should have said that and covered the whole thing.

As it is, I think you should finish it. You’ll never be able to trust him. He could get you somewhere lovely then start nickel and dime-ing you, making barbed jokes about you being a kept woman etc.

Honestly I have the nick just reading about him. Bear in mind if you finish it, he’ll frame it as you being a gold digger who objected when he expected you to pay for your own holiday. Because that’s how his mind works.

calling previous women gold diggers was red flag 1. Don’t ignore red flag 2.

Have you met his friends and family OP? Are they all well off? Realistically this isn't going to work.... were the other women gold diggers? I would constantly feel inferior and YES he is tight also!

Tell him to go without you.

You'll not enjoy it either way. Either you'll be stressed every time he orders a bottle of wine with lunch. And mentally adding up your share, and sticking to tap water.

Or if he agrees it's his treat and you'll feel like you're compromising your ideals. And he'll likely go on and on and on about how he's treating you.

I think your approach here is absolutely sound and it’s what I would also be thinking. You don’t want to sponge and scrounge, nor do you want to have unexpected expenses. It’s about being responsible but also him recognising that you can’t really be offering to meet him half way on a trip when you get there if it’s suddenly going to be a millionaire’s budget kind of experience. As with any holiday you’d book for yourself, you need a sense of the expected expenditure.

I’m not sure he’s testing you in an unpleasant way, more that he’s happy to pay but is probably wondering if you’ll willingly seize this with both hands or if he’ll learn something refreshing about your own attitude to his money. I can understand that given that he’s hugely wealthy and has bad luck with gold diggers. It’s going to be pleasant for him to realise that you genuinely aren’t like that.

Do exactly what you are thinking. Insist that you’d like a clearer sense of what to budget for and explain that you expect to be contributing, but not in a reckless ‘bung the bill on the credit card’ way once you get there.

Yes. If he wants her to contribute, he needs to share the decision making with her, and let go of some of the control that comes with paying for everything.

It is so weird!

He wants to celebrate and he wants to go big. He knows you can’t really afford it. I would say it’s up to him to pay as he has invited you, instigated the whole thing.

Otherwise I think it might’ve curtains as he’s not generous. He’s mean.

Just tell
him what your budget is for such a holiday. He then has 3 choices.

• he pays for a fancier holiday including your expenses over what you want to pay, if that’s what he wants
• you both agree on a holiday which is within your budget
• he goes to at Bart’s on his own

I’d even question if previous partners were gold diggers or just unable to keep up with his lifestyle. It seems nuts that he wants a holiday to celebrate a windfall but expects you to contribute without the windfall.

I guarantee you if he liked you enough he wouldn’t be mentioning gold diggers or anything of the kind. When men fall in love they just want to make you happy. They’re not haggling over the bill. I bet if you throw him back, you’ll find him at some point with someone who isn’t paying for a single thing.

The repeated gold-digger comments would annoy me, and I'd take this opportunity to mention that. He's the one who chose to date these women! It's unattractive of him to now insult them.

I'd tell him plainly that if he finds your financial independence so attractive, he needs to accept that this means means you're not happy to spend huge amounts of money to go to a destination of his choosing, particularly not without any warning of how much it might end up costing.

He wants this holiday to be a certain (expensive) way? Very well, but he ought to be generous and tell you up front that he'll cover the costs. He can apparently afford it, and accepting a holiday from him doesn't make you a gold-digger.

I think you are overthinking it. He wants to go on a great holiday with you. He said he will pay for the flights.

Work out what you are prepared to spend and say " this will be my contribution".

Then go and have some fun.

Or maybe his previous partners were gold diggers. That's enough to put anyone on the defensive isn't it.

Dating for 15 months and always shared expenses? Hes sold his company - bloody let him treat you! Money is no object it seems at the moment, so relax and enjoy!

You are right in wanting to know what other costs might be. You need to say to him, I only have XX to spend , will that be enough. He needs to be clear that you can't afford this holiday. You don't need to ask him to pay for you, he can offer if he really wants to go there.

Reading between the lines he’s offering to pay for it all! He just doesn’t want to offend you by saying ‘let me get this’. He’s thinking she’s independent and astute but am I fuck going to Corfu when I can afford the best of the best in St Barts! I’d say ‘all sounds amazing, can’t wait, you sure you’re ok paying my flight? St Barts might be pricey, I’d better up my limit on the old credit card!’

Just relax, enjoy it.

If he's offering to cover the cost for a blow out holiday you didn't choose then why not? If he's not offering to pay then you need to work out what you'll contribute in advance, otherwise it will be a stressful holiday for you. If I had his money, I'd offer to pay for an unusual one-off massive expense. It's not an insult to your independence. If he was offering to pay for everything day to day that would be different.

What a prick. I'd tell him to go with a friend instead of me if he's going to be like that.

How hard would it be for him to say 'I enjoy that we do things equally, but I'd like this to be my treat.'

There is a reason why people with similar finances and sokolov backgrounds end up together. If you want this to work he needs to let go of the gold digger thing and you need to be less independent.

At this point in time all you can do is communicate. Either you go on holiday with your budget or he pays for it. It has to be agreed beforehand and not just sorted at the place. That can only be done if you have similar finances. Tell him that you like him and don't mind paying your own way but you can't go to debt because he is a millionaire. And also that him sometimes offering doesn't make you a gold digger. Frankly he has such a twisted views kn gold diggers that it is a bit of a red flag.

Either he pays for everything for the expensive trip or you split costs and go for something within both of your budgets.

Yes this