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Cancelling First Date Help?!

108 replies

CheeseSandwich1 · 21/10/2025 18:38

I (late 20’s) met someone (late 30’s) on a dating app.

Talked, swapped numbers and a couple of days later he asked if I’d like to go on a date. I agreed and he suggested a very, very nice place. I let him know I didn’t expect to go somewhere like that for a first date but he said he was more than happy to go and that it would be ‘his treat’.

I now want to cancel the date. He seems lovely but I feel a bit inferior after talking more and my confidence is lacking. The only problem is I’ve looked on the website and he will have paid a hefty deposit to secure the booking. I feel awful if I cancel as he’ll lose that money.

What do I do?! Just go and get it over with?! Or cancel?!

OP posts:
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HoskinsChoice · 23/10/2025 08:37

@CheeseSandwich1 When is this date and did you go/are you going?

Helpel · 22/10/2025 13:31

if you’re taking about what wealthy men ‘normally go for’, they go for looks and youth. You’ve already ticked one box being 10 years younger. He’s seen your pics so obviously thinks you tick the second box. A rich man doesn’t need a rich woman.

Cosyblankets · 22/10/2025 13:26

CheeseSandwich1 · 21/10/2025 18:58

I’ve been to quite a few Michelin star places as food is my thing, hence him booking it! I just don’t feel comfortable with someone else paying for me but I also don’t want it to make it into a big thing!

I have no idea what to wear?! As I’m sure he’s used to tiny dresses and big heels - those girls look amazing but I’d look ridiculous!

If he wanted the high heels lips botox etc surely he would have gone for that.
He saw your pic
He liked it
Go!

Aposterhasnoname · 22/10/2025 13:19

CheeseSandwich1 · 21/10/2025 18:58

I’ve been to quite a few Michelin star places as food is my thing, hence him booking it! I just don’t feel comfortable with someone else paying for me but I also don’t want it to make it into a big thing!

I have no idea what to wear?! As I’m sure he’s used to tiny dresses and big heels - those girls look amazing but I’d look ridiculous!

If you've been to many michelin starred places then you should know exactly what to wear. The same as you usually wear to them. If you think that women are turning up to that type of restaurant in "tiny dresses", then I suspect you haven't been to as many as you suggest.

ForZanyAquaViewer · 22/10/2025 12:48

This is such an irritating post. You’ve flattened people into stereotypes: the self-made man with money, the Love Island type girl, the horsey country sort, and the light-tan, lash-lift, cashmere brigade. People are more than clichés.

I just don’t understand the urge to paint people with such broad brushstrokes. He’s seen what you look like. You’ve seen what he looks like. You’ve chatted. You like each other. You’re going on a date. You’ve eaten in enough Michelin-starred restaurants, by your own account, because you’re a foodie. So wear what you’d normally wear and act how you’d normally act. If you can’t or don’t want to, then don’t. Cancel the date. He’ll cope.

everychildmatters · 22/10/2025 12:26

@Bushmillsbabe This. One guy I was dating (after a number of dates before) offered to take me to London for the weekend - restaurant, show, hotel etc. Despite my better judgement I agreed and then when we came home he actually said "I did all this for you and didn't get any @@@!"
I dumped him with immediate effect!

Bushmillsbabe · 22/10/2025 12:18

youalright · 21/10/2025 19:03

Someone paying that amount on a first date would make me really uncomfortable is it in a hotel

This, I wouldn't worry I wasn't 'good enough', but I would worry it might come with 'strings attached'. Not that you are of course under an obligation, but the concept might make me uncomfortable and not really enjoy the date. It also depends a bit on the messaging phrasing, if its 'I have been wanting to try that place for ages, it my treat if thats ok with you' would me much better than 'I can afford it and I'm paying so that where we are going' type.

AuntyVibes · 22/10/2025 12:11

Hi OP,

Rather than cancelling, could the restaurant booking be postponed until you know each other a bit better? Surely the restaurant would be happy to move the date?

I suggest going on a coffeee date / walk in the park date first.

You should never compare yourself to others, you have alot to offer and need to love and appreciate yourself first before anyone can love and appreciate you.

Also why would someone with wealth look down on someone from an ordinary background?

Never underestimate yourself and don’t prejudge a man you never met because he has money.

Take it slow and trust your intuition and don’t be ruled by fears.

Some nice jewellery and classic clothing can just be as nice as tight and short skin revealing items, better even. Who needs Love Island types for a LTR anyway, those relationships are not based on importance values the majority of the time.

Good luck and best wishes 🧚🏼💐🌸

2025TTC · 22/10/2025 08:51

CheeseSandwich1 · 21/10/2025 18:38

I (late 20’s) met someone (late 30’s) on a dating app.

Talked, swapped numbers and a couple of days later he asked if I’d like to go on a date. I agreed and he suggested a very, very nice place. I let him know I didn’t expect to go somewhere like that for a first date but he said he was more than happy to go and that it would be ‘his treat’.

I now want to cancel the date. He seems lovely but I feel a bit inferior after talking more and my confidence is lacking. The only problem is I’ve looked on the website and he will have paid a hefty deposit to secure the booking. I feel awful if I cancel as he’ll lose that money.

What do I do?! Just go and get it over with?! Or cancel?!

Hi,
No judgement at all and you can only do whats right for you.
In my oppinion your worrying before you have even had a chance to meet the fella, he could be looking for someone who isnt influenced by wealth or superficial beauty, he looked at your profile and wants to meet with you, confidence comes from within not whats on the outside, put your fears to the side and you could possibly end up having a really nice time with this chap and possibly a second date, dont worry about your differences and focus on the things you have in common, its a first date after all. Good luck xx

skippy67 · 22/10/2025 07:56

treesandsun · 21/10/2025 23:56

I'm going to go against the majority and say don't go. If everything you have said is genuine, I don't feel that you are ready to date. You're also quite judgmental and have made a lot of assumptions about somebody based on your own biases.

Yep. Don't go. You sound like extremely hard work.

aCatCalledFawkes · 22/10/2025 07:49

I think its nice that he has just a normal dating profile.
I met my boyfriend of a few months online and also had no idea he was a high earner (who says that on there dating profile anyway?), he does pay for a lot of meals out but I insist on getting a round of drinks in or if its a meal at his house I bring a bottle of wine over. All stuff that I know is appreciated and despite his earnings he has a relatively down to earth life, i.e. lives in a normal house, pretty standard car, his children are pretty average at school etc....

OrlandointheWilderness · 22/10/2025 07:36

Look, you aren’t being fair to him. You cannot make snap judgements about people based on what you think they will like - you don’t know him.
so far we know you both like nice places to eat so you clearly have something in common so just go! It’s one night, you might actually really like each other and if you don’t it’s not a problem is it.
People don’t do well put in little stereotypical boxes. We like who we like - maybe he’s had enough of the fake look for a lifetime?!

TakenewNn · 22/10/2025 00:17

treesandsun · 21/10/2025 23:56

I'm going to go against the majority and say don't go. If everything you have said is genuine, I don't feel that you are ready to date. You're also quite judgmental and have made a lot of assumptions about somebody based on your own biases.

I agree

WatchingTheDetective · 21/10/2025 23:58

Why are you making all these assumptions about this poor man? Go on the date and get to know him. Judge him for who he is, not what you assume he is.

treesandsun · 21/10/2025 23:56

I'm going to go against the majority and say don't go. If everything you have said is genuine, I don't feel that you are ready to date. You're also quite judgmental and have made a lot of assumptions about somebody based on your own biases.

Waterbaby41 · 21/10/2025 23:21

For goodness sake, stop being so horribly judgemental, go on the date and let him make his mind up what type of person he wants to date. It's you he has asked, not some Love Island lookalike.

lilybit2025 · 21/10/2025 23:21

Can I also say majority of men do not like the fake look and much prefer natural looking women.

lilybit2025 · 21/10/2025 23:16

Please go! You never know what could come of it. Money doesn't make someone superior to you. He's likely worked incredibly hard to get to where he is. He is still an ordinary person. Do not judge him on his money, if anything, enjoy it!

idri · 21/10/2025 23:14

Can totally relate to feeling as though you’re inferior (even though you shouldn’t feel that way).

Definitely go on the date though! You don’t have to see him again if it goes terribly etc. A free meal in a nice place sounds like the absolute dream!

Blownupblowndown · 21/10/2025 23:13

CheeseSandwich1 · 21/10/2025 18:41

It turns out he’s a wealthy businessman. From his dating profile it looked as if he had a ‘normal’ job but turns out he doesn’t do that job, he owns the company and more.

I just thought men like that would go for ‘Love Island’ type girls with lots of cosmetic surgery, tight clothes whereas I’m more of a natural look. I don’t even know what to wear?!?!

It’s not a removal/delivery company is it?! Lol.
there’s a bloke going round on the ‘any tea?’ App about a bloke who claims to be a wealthy business owner who takes girls to fancy restaurants as ‘his treat’

CalmTheFuckDownMargaret · 21/10/2025 22:41

CheeseSandwich1 · 21/10/2025 18:41

It turns out he’s a wealthy businessman. From his dating profile it looked as if he had a ‘normal’ job but turns out he doesn’t do that job, he owns the company and more.

I just thought men like that would go for ‘Love Island’ type girls with lots of cosmetic surgery, tight clothes whereas I’m more of a natural look. I don’t even know what to wear?!?!

You’re probably the very thing he’s looking for. Kind, not a gold digger, authentic, natural. You could make each other really happy. Just be honest - tell him for a first date you’d like to go somewhere very relaxed but you’d potentially love to go there with him at a later date! If I were him, I’d think this was lovely. It shows you aren’t just after a fancy meal at his expense.

SnowflakeSmasher86 · 21/10/2025 22:37

CheeseSandwich1 · 21/10/2025 18:47

Yes. I don’t use filters and there’s a clear full length pic. I’m not saying I’m unattractive. I just have more of a natural look than girls I think he’d like?!

I tend to see wealthy men with girls who are more of a filler, botox, surgery, tighter clothes, fake lashes and dark tan. I’m more light tan, lash lift and a cashmere jumper!

And then “I have no idea what to wear?! As I’m sure he’s used to tiny dresses and big heels - those girls look amazing but I’d look ridiculous”

It doesn’t sound like you feel inferior OP, it sounds like you think you’re much better than “those girls”. You are being disingenuous when you say they look amazing, as you’ve described a very particular look, and then yourself as “lash lift and cashmere”. Just admit it, you think you’re classy but dressing it up as being ‘inferior’. Stealth boast much? AIBU - This rich successful businessman wants to take me on a date to a fancy restaurant.

Stop being so looks obsessed and find out a bit more about him as a person. Wear whatever you would normally wear when you go to a Michelin star restaurant, as you say you have.

everychildmatters · 21/10/2025 22:30

@Bobiverse @TakenewNn Well I'm married now, but when I was dating I was definitely looking for an equal relationship. Personal preference was I didn't want someone "treating" me; and more so someone I'd never met. I can pay my own way - did do and still do.

StokePotteries · 21/10/2025 22:04

OP, you really don't need to take it so seriously. In the past I've been on dates with a rock star whose coat cost more than i esrned in a year, a very pretty but cheesy international playboy type who rocked up in his Rolls Royce and several other men who I knew I wasn't right for but it was fun for a while. Let a bit of glamour into your life and have fun.

Bobiverse · 21/10/2025 22:02

everychildmatters · 21/10/2025 21:35

He wouldn't be my cup of tea, but if that's the sort of relationship you're looking for then go for it!

What specifically would not be your cup of tea? You know nothing about him other than he has grown up kids and earns well.