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.

I would say your values don’t match. You like to plan and save and be clear in communication, he likes the adrenaline ride. His attitude to women is not very respectful either.
I don’t think he sees you as an equal partnership as he’s quite patronising too. At what point in a relationship does a girlfriend become a ‘gold digger’? Probably when he wants to do something that she can’t afford.

I think it might be time to have a full, frank discussion about finances, he can't just use it like a sword of damocles hanging over you.

He has to acknowledge that he is immensely wealthy and it is vanishingly unlikely that he will ever find a partner that will be able to match his spending, therefore, he will have to pay for other people to do stuff he would like to do.
Also I am sure with his amount of money, he will have had gold diggers pursuing him which I can imagine is dehumanising and tedious.
He is probably super sensitive to this which is why he keeps mentioning it and he needs reassurance that you are not a gold digger.

You have to acknowledge that if you want to stay with this man, that you will have to let him pay for stuff and become comfortable with that. Otherwise, you both will be doing things that only you can afford - in which case, what's the point in him having £100m and you can't enjoy it?

My friend went out with someone incredibly wealthy - although not as minted as your DP. They had a set up similar set up to you, in 'normal life' they went 50/50. If they went on a posh holiday, she paid him what she would normally pay for a holiday e.g. £2k; he would pay for everything else e.g. £8k. It worked really well for them
Float this suggestion to him

BTW - he needs to acknowledge that you're not a gold digger and at this stage of your relationship, he should trust you

One last thing, if you are getting miser vibes from him, IMO this one of the worst attributes to have in a partner, particularly if they are well off.
You don't want your partner to be a spendthrift but equally off-putting is wealthy penny-pinching traits.

Even resolving the holiday isn't going to help in the long term.

Firstly his attitude isn't going to change.

Secondly, what about everything else you do together? The party you go to, where your clothing isn't ‘expensive’ enough for the company he keeps, the meal out, where you are paying more than you are comfortable with, to go halves, a car/house that you want to equally own?

This isn't going to work as it is now.

He doesn't actually sound nice. I think you could do better, op.

Tbh, you don't sound like a gold digger & I applaud you living within your means & doing well for yourself. The boyfriend on the other hand, sounds a right miser. Surely, if he's THAT wealthy or just on his $2m salary alone, he could treat you to the trip. I bet the other ex girlfriend's were not gold diggers either. He is just stingy.

Here's a question. What would you do in his situation? The answer should tell you if you are both in alignment or not. If you're not, this won't last. Sorry.

I'm all for paying your way and not creating a situation where there's a power imbalance. In a situation like this though I'd expect him to pay for the holiday.

He’s so lucky to have you in his life. I’m not sure he’s going to come out on top over this though. His behaviour is very odd.

@KThughes What are you hoping to get from this st bart's convo with him?

why don't you say how you feel about him/he you; and generally how your relationship is?

everything sounds weird.

If he wants to celebrate a windfall by going somewhere few can afford, then he needs to pay for both of you. How can he expect you to have the same disposable income as him? It's nonsense that he won't even tell you what your share of the bill would be but he expects you to say yes anyway.

I'd be getting the ick from his sheer silliness.

The more you post the nastier he sounds Op. I think you might be coming to that realisation too.

He sounds horrible. Sorry. It would no longer be about the holiday destination and expenses, or finances generally. If he won’t listen to you about this, and is nasty about women generally, do you want to go out with him at all?

So what if he thinks you’re a gold digger. Do you actually care what he thinks after all this? I’d get shot of him, life is too short for this level of anxiety (over a holiday for goodness sake! What will he be like over something more serious)

What a total tightarse this bloke is! Can't believe he's trying to make you pay half for this trip. Lol! What a total joker.

He'd be getting dumped.

I would just say to him....
I have £5000 (or however much you decide) to spend on holidays this year. I am willing to give that to you towards the St Barts trip if you cover the rest. Although its not a destination I would choose, I understand this is a big deal for you, and you want to celebrate in this particular place so I will go along with it. Its always my preference to cover myself financially, however I am only able to do that because I am careful and stick to my budget. So I hope you respect that, and if you decide you would rather not take me on this occasion I understand, and would be happy to have a Cotswolds holiday with you when you return.

Or something like that. Upfront, honest, and to the point. Any decent person would respect that.

I would now be worried, even if you had agreed to contribute your budget, that'll you'd get out there and be put in a situation where you have no choice but to use your credit card (because he won't for eg pay for your half of a meal/outing etc). So even if he offered to pay I think the trust would be gone for me, given that his initial decision was to "work it out when we get there".
I think this relationship would be over for me. It sounds like you've decided not to go - stick with that decision!

I agree. Eg 'I have a £3000 budget including everything and can't go over that.' If he wants to top it up he can do. But if a rich person insists on doing 50/50 with a poorer person then they need to slum it at the poor persons budget.

I like that idea - you get this trip I'll get the next one when I'm celebrating something for me - then you can celebrate your next promotion on a long weekend in Barcelona etc

Yes that's how the tinder swindler worked!!

I'm not getting any sense of what he brings to the table for you OP. My red flags would be waving when he called other women gold diggers and would definitely be going off at him dismissing his wife's work as a SAHM. He doesn't sound like he likes or respects women much. Does he worry as much about male friends taking advantage - bet he doesn't.

Of course there is no need to pay for your holiday a year into the relationship. But pressurising you to spend more than your budget to go to the destination of his choice to celebrate wonderful him is not nice. I don't like him.

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

I'd have laughed at this point and said, 'I can't afford a holiday in St Bart's and I'm not interested in spending stupid money just because you fancy going there. Have a good time'.

I agree with a lot of the others that he sounds unpleasant, to be honest. Massively wealthy but tight doesn't hold any appeal to me. He also sounds like he doesn't really understand the realities of life for most people and I'm turned off by men who are dim and lack empathy.

He expresses contempt for the woman who raised his children.

He is conditioning you by complimenting your independence hoping that his compliments will be valued highly enough for you to learn not to become like his "gold digging ex".

He's pretending he can't understand why you need to know about the potential cost of the holiday up front, that's borderline gaslighting. Few people get to be that rich (in my experience) without knowing the cost of everything.

Tens of millions in the bank and won't even pay for a holiday. Someone needs to tell him there are no pockets in a shroud.

He doesn't sound like a keeper.

Better a poor man who will share his sandwich with you than a rich man who will make you pay towards a posh meal you don’t want.

All day, every day 🙌🏾

@KThughes any update?