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.

If he wants a blowout then his treat. Otherwise no. He sounds gas lightly and tight.

He sounds awful, there's zero way I would be going. Even if he turned round and said he would pay for everything, you just know he'd be mentioning it and totting up the amount in his head to throw against you on some future occasion.

Besides once you get above a certain amount of spending i'm not sure how much better a holiday can be. I would say you can do 5 star wherever you can comfortably afford, but he will need to go to St Barts on his own.

How about “for fuck sake, I get you got stung with exes who tried to rip you off, but can you drop the bullshit about being so glad I’m not a gold digger? I will pay my way, but that also means you don’t get to set the budget or decide where we go. I set my budget when I am expected to pay, and I decide where I want to spend my money. If you are going to pay for me, say so. If I am paying, accept you don’t get to make all the plans alone. I am done playing games because you aren’t over your exes.”

Tho, OP hasn't been back anyway! But if a waste of time so far!

Icccck. I feel gross for you!

if he’s inviting and suggesting and pressing you go to a certain place out of reach for you, then yes, he should pay. I don’t think it’s reasonable for him to expect others to spend like he does.
and ewwww, calling other women gold diggers? Just this would have me running for the hills.

I had a friend who was dating a wealthy man when she had far less disposable income. He addressed it quite early on by saying he didn't want her to get into debt for their social life and he was more than happy to pay for meals, weekends away etc. It was still an equal relationship as she brought lots to the relationship that he was missing in his life. All resolved through a clear direct conversation, like the op is trying to have.

"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, ..."

This is the point in your post, @KThughes , where my radar started pinging.

1. He has no need to refer to women he has dated. No need at all.
2. There are echoes of all those men who loudly proclaim that their ex was a crazy bitch and that's why he doesn't see his children / want to marry / pay his share. It invariable turns out that his Ex is not a crazy bitch and is glad to be shot of him.
3. It is not a 'sentiment' he is repeating - it is an 'instruction'. He is telling you not to expect generosity of him, or you too will become a 'previous partner' who is a 'golddigger'.

"He said he’d pay for my flight and we could ‘figure out the rest while we were there’."
Nope. Nopity nope, all the nopes with a big side order of 'are you fucking kidding me?!?'. There is no way on this earth that I would agree to this, not without knowing what costs I would be incurring. And even then, I would be considering whether this holiday was worth that amount of money to me.

I would be VERY suspicious of this. Many wealthy people maintain their wealth by nudging other people into paying more that their fair share. His sudden vagueness over costs makes me think that could be his aim here. By paying your fare, he places you in a position of obligation. And places himself in a position of power. I think your 'gross' feeling has been sparked by your instinctive understanding of that, and of how that could play out.

Personally, I'd be refusing to go on this holiday, and suggesting he take his two children instead. I'd also be reconsidering the relationship. Possibly just holding it a little more 'arm's length'. Possibly winding it down and letting it wither on the vine. But the relationship has changed, and he's the one who has changed it.

If it is a one off trip to celebrate a big financial gain - going to a destination that is not within your budget then on this occasion he should treat you. It not about being a gold digger. If he wants you to go he would treat you. If it was just a normal holiday to a mutually chosen destination then you should pay half.

You sound great. I don't like the fact that you must feel under such pressure to show him that you're the opposite of his exes (IF they even were golddiggers 🙄).
You've already proven that.
The kind thing for him to do, under the circumstances, would be to offer to take you on holiday ... and pay.
I don't like that he's being so cryptic about it.

He pays for the whole trip or you have a say. Simple.

OP you sound lovely, too lovely for him.
from what I’ve read, I’m not keen on him. I don’t like this gold digger almost gaslighting chat.

if you do decide to go, make sure you have enough money to get back home 🏡 in case you need to

I really wouldn't be happy just assuming that he was going to pay for the majority of expenses on holiday. What happens if that was not his intention?

I would want to be clear and to know that we shared a common understanding of who would cover the expenses before committing to go on the holiday.

Thank you for all your responses. I slept on it last night after I reiterated that I couldn't say 'yes' to expenses that could be anything from £1k to £20k. It just makes no financial sense. He said he's 'obviously not going to want to go 50/50'. Whilst I appreciate that (even though it still makes me feel a little uneasy), a single night in a hotel is £1000pn. Food can easily be £500+ day on the island. Alcohol also is the killer expense.

Being told to 'relax' again (by him) doesn't help. I'm obviously not asking for a 'free holiday' as I'd happily stay home than be worrying the entire trip about the expenses - especially if it means I'll end up with an eye-watering bill. I am quietly proud of having no debt and quietly proud that I manage my money well. To put myself into such a situation is just plain stupid.

I'm sorry he's had bad experiences with 'gold diggers', but much like the other posters, how do we even know they are/were 'gold diggers'...? I'm getting sick of 'proving myself'. I've been only too happy to take it in turn to pay for things as that is, of course, fair. He doesn't need to keep repeating how nice it is that I am independent. I know I am and I do not need this validation. To be clear, it's not like he pays for 5 star experiences and I pay for a drink in a pub. Not at all. It is all very 'level' in terms of experiences/dinners. St Bart's is obviously not that though.

I suggested a weekend away in the Cotswolds, which he shut down and said he wanted to 'celebrate'. We are going in circles.

Then he will have to let the moths out of his wallet if he wants his special holiday. Honestly he is a fool

Agreed. Honestly, this whole thing has put me off. I am financially independent because I haven't been spending recklessly - so why would I start now..? It feels like he is holding his money/status over my head - and it's really bizarre and so unattractive. I truly am not being 'bitchy' when I say I would much rather stay at home (and not take any time off work) to go on his tropical holiday.

Tell him to go celebrate on his own.

I suspect all this gold digger talk is designed to make you feel anxious and like you have to prove yourself.

That doesn't mean saying yes to things you can't afford.

I'd say no, not going, can't afford it.
If he offers to pay any part id say and have you throw that in my face later that I'm a gold digger? No thank you. My rule here is if I can't afford it, I don't do it.

My partner is wealthy. When we met I was well paid and independent, but my income was from a regular job, my money was nowhere near what he had. It was awkward at first, but one day he suggested that I could provide the picnics, he'd take us out to the Ritz, I could sort the day trips to Brighton, he'd take us to the Grand Prix. Both of us enjoying our time together and being able to relax was what was important.

No good man would be happy to put you under financial pressure or want you to stress like this over a holiday. He knows what he's doing. It's not gold digging to be practical and recognise that if one partner has a massive disposable income it's not a big deal for them to fund some amazing trips for both of you.

He's being really unfair to you. Tell him you need to go somewhere you can afford, because you're not getting into debt for a holiday, otherwise he's paying and all this not knowing is unfair and stressful.

It is a really bad sign that he tells you to relax. That feels like a power move and he will give you the bill whenever he feels like testing you. He needs to either say "I got this" or "how about you give me £x and I cover the rest" or something if he actuslly wanted to make you comfortable. Sounds like he enjoys the power 🤷🏼‍♀️

I'd say to him that this is making you too stressed to go on holiday since you have no idea if you will be expected to spend your lifesavings or not. So either he will have a real audit conversation about money or you go to cotswolds together and he will go to St. Barts with someone else.

If you're going round in circles op, sounds like you need to say something like this!

Reminds me of this reddit story
https://www.reddit.com/r/BestofRedditorUpdates/comments/17w3kic/final_updates_wibta_for_calling_off_a_wedding/

Being so mean when he has so much money is such an unattractive trait. Testing you like this is also really unattractive. You sound great. Do you really want this complete prick in your life?

When i was with ex i paid 3k for holiday he just had to find spending money...took him to europe too etc. another ex i took him to expensive spa and japanese tea ceremony...i have learned my lesson though. These guys are spongers...i would never do it again. Pay your own way or i go alone. Im sorry this is happening to you OP. I wouldn't go with him on holiday unless he paid own way...but tbf i wouldn't be with him now

He said he's 'obviously not going to want to go 50/50'.

He’s playing games with you.

Tell him that you’re not going, take back control.

He’s being really controlling/duplicitous. I’m not sure the word I’m looking for, but he’s expecting you to make yourself really vulnerable. He is doing the whole ‘relax, you’re making a fuss about nothing, you know how much I admire your independence…’ while not giving you the information you need to make a responsible decision. He’s expecting you to hand control to him. And that’s just the first step.