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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:
TakenewNn · 21/10/2025 20:37

In the kindest way, you need to get over yourself. Just go on the date and see what happens. What’s the worst that could happen?

ainsleysanob · 21/10/2025 20:37

youalright · 21/10/2025 19:30

Maybe, I just know people who have been in this situation. The man ends up being married and has different women at all his business trip locations. He wines and dines them pays for everything including the hotel room for the night.

Bloke I know doesn’t have a penny to scratch his arse with was watching telly with his wife about 18 months ago at his home in South Yorkshire, when his wife scrolled through Facebook she saw he’d been tagged by his secret’ girlfriend’ at their baby shower, in Birmingham. For their second baby…. 4 months ago, it came to light he’d also got a third family! Those construction labourers don’t half get about! It’s got nothing to do with them being rich m, it’s about whether they’re a twat or not.

CheeseSandwich1 · 21/10/2025 20:33

TableLegs001 · 21/10/2025 19:51

I think I would be wary if this guy already has an ex-wife and children. Paying for an expensive meal for someone he hasn’t met is extravagant. Coffee or drinks would make more sense (if you met for mid-afternoon drinks then off to dinner if things click). I don’t think OP that you should bring the insecurity about looks into the whole thing or say anything about your worries to him either. I can just see some man being ‘charmed by the freshness of it compared to all other girls’ (aka knowing he can take advantage).

If this was my DD going, I would be a little worried.

He doesn’t have an ex-wife, he had children very young so they’re grown up. I haven’t told him about my insecurities and I probably come across very confident to him.

I think it’s more that I’m worried I’m not his type. My ex is quite wealthy but in a horsey/farmer type way so his type was more country girl which I guess is more me. He’s clearly self made and I know it’s a vast generalisation but I tend to see men like that with more ‘done up’ women.

OP posts:
Skippydoodle · 21/10/2025 20:32

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?!?!

Just go. Don’t fret, you will click or not - luck of the draw! Could be fabulous or disastrous. Let us all know, fingers crossed for you xx

CheeseSandwich1 · 21/10/2025 20:29

AutumnCosy2025 · 21/10/2025 19:47

Well, of course that happens, but so do 'dates'

💁🏻‍♀️

and dinner at a run of the mill restaurant doesn't mean he's not married

He absolutely is not married. He doesn’t live too far and his socials show he is clearly not married. He has children but they’re grown up as he had them very young.

OP posts:
roycroppersshopper · 21/10/2025 20:05

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 thats why you should go. He chose YOU. Yes, you! Based on your clear pictures, he knows what he is getting and wants to date you. Have a word with yourself and go.

What do you have to lose? About 3 hours of your life. That's all.

Go and report back, I want to know how it goes.

MyLimeGuide · 21/10/2025 20:00

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?!?!

Nooo way!! Go for it girl!!

MoominMai · 21/10/2025 20:00

Owlmoonstar · 21/10/2025 19:14

Light tan and lash lift. If that's natural then god knows what I am. A sewer rat? 🤣

You'll be fine. Do it and chalk it up as life experience.

🤣

This made me chuckle lol. I must be a creature of the night as well haha. I will dab some concealer on any blemishes but that’s it! Ya take it or leave it! 😅

racierach · 21/10/2025 19:59

Why would you presume that’s the kind of girl he prefers ? I don’t understand your logic.

TableLegs001 · 21/10/2025 19:51

I think I would be wary if this guy already has an ex-wife and children. Paying for an expensive meal for someone he hasn’t met is extravagant. Coffee or drinks would make more sense (if you met for mid-afternoon drinks then off to dinner if things click). I don’t think OP that you should bring the insecurity about looks into the whole thing or say anything about your worries to him either. I can just see some man being ‘charmed by the freshness of it compared to all other girls’ (aka knowing he can take advantage).

If this was my DD going, I would be a little worried.

IvePiercedMyFootOnASpike · 21/10/2025 19:51
  1. Go. Be safe.
  2. Be yourself/ wear your usual style
  3. Most important: Let us know how it went 🙂
AutumnCosy2025 · 21/10/2025 19:47

youalright · 21/10/2025 19:30

Maybe, I just know people who have been in this situation. The man ends up being married and has different women at all his business trip locations. He wines and dines them pays for everything including the hotel room for the night.

Well, of course that happens, but so do 'dates'

💁🏻‍♀️

and dinner at a run of the mill restaurant doesn't mean he's not married

Sassylovesbooks · 21/10/2025 19:38

If this man had wanted Miss Botox, with her fake eyelashes, fake tan etc, he'd have chosen a woman who looks like that. He's chosen you! He probably didn't tell you he owns a company, or made it common knowledge on his profile, because he knows it would attract women, who are only interested in what he can give them. You don't have to wear a little black dresses with heels, if that's not your style. What is your style? What about a jumpsuit? There are some gorgeous ones around. He likes what he sees, don't try to talk yourself out of the date, by imagining what you think he should want in a woman. The only way to overcome your fears is to face them. Cancelling the date is running away. You liked him enough to give him your number, so go on the date, see if there's chemistry. If you cancel, you'll never know if this man might have been the right one for you. I met my now husband online dating, 19 years ago - it does work - but only if you go on the actual date!!

Cucy · 21/10/2025 19:31

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!

Where do you see these men?

On social media where everything is fake?

I too panic like this.
But what is the absolute worst thing that’s going to happen - not much.

It would be much worse for this poor man if he thinks you’re not interested or was wasting your time.
So think of it as you’re doing him a favour by going.

Please update us afterwards!!

youalright · 21/10/2025 19:30

AutumnCosy2025 · 21/10/2025 19:12

The man has money, he wants to go somewhere he enjoys. He's happy to treat the OP. Having money but feeling forced to eat somewhere more 'main stream' is a bit miserable. He wants to have a nice night out, with a self acclaimed 'foodie' who will appreciate if (unlike me 😂😂) is not a bloody crime.

Maybe, I just know people who have been in this situation. The man ends up being married and has different women at all his business trip locations. He wines and dines them pays for everything including the hotel room for the night.

Thistooshallpsss · 21/10/2025 19:23

My mum think late 1940s with a council house upbringing seemed to date a few wealthy men and went to dinner at one man’s house where is was asked by the father where she lived then asked how many acres? !!!! She must have carried it off she always did

RitaFromThePitCanteen · 21/10/2025 19:21

I think instead of making assumptions about him (that he can only like women with fake tan and fillers) you should judge him based on the evidence: he invited you out for dinner. Therefore he (presumably) likes the look of you.

Go as yourself. Wear something nice that you already own. Don't stress too much. You aren't beholden to seeing him again if things don't feel right.

londongirl12 · 21/10/2025 19:19

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!

Wow. Don’t judge the poor man before you know him! He must like you otherwise why would he waste his time.

gannett · 21/10/2025 19:16

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 was attracted to "those girls" he would be dating (or trying to date) them.

He is dating you for who you are, he does not expect or want you to try to be a different kind of woman. Wear what you like to wear.

If you're into your food and he's picked a fancy restaurant then I would assume that firstly he's trying to impress you with something you'd be into, and secondly if he's into food too then I imagine that's what he thinks you'll bond over.

(People who go to Michelin restaurants tend to really enjoy talking about food!)

Aside from anything else it's got to the point where it's too rude to cancel unless you have a very good reason (like, you've discovered something horrendous or unsafe about him). So go, enjoy the food and the absolute worst it'll be is a slightly awkward evening.

ACynicalDad · 21/10/2025 19:15

just go, but him losing that deposit will feel much less than you using it if you decide not to go

AutumnCosy2025 · 21/10/2025 19:15

Summerhillsquare · 21/10/2025 19:05

On the contrary OP they like women they can feel powerful over. I'd be wary of that.

'They'🙄🙄🙄🙄🙄

Says more about you than this man.

Owlmoonstar · 21/10/2025 19:14

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!

Light tan and lash lift. If that's natural then god knows what I am. A sewer rat? 🤣

You'll be fine. Do it and chalk it up as life experience.

AutumnCosy2025 · 21/10/2025 19:12

youalright · 21/10/2025 19:03

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

The man has money, he wants to go somewhere he enjoys. He's happy to treat the OP. Having money but feeling forced to eat somewhere more 'main stream' is a bit miserable. He wants to have a nice night out, with a self acclaimed 'foodie' who will appreciate if (unlike me 😂😂) is not a bloody crime.

Bobiverse · 21/10/2025 19:11

Just go!
I’m late 30s, single mum. And I met a guy through online dating who is late 40s and I thought he had a normal too. But turned out he’s a vice president in a bank, and wealthy. I am about as opposite of “love island” as you can get. It doesn’t matter! If your photos are truthful then he knows what you look like. It doesn’t matter. The difference in finances doesn’t matter. We’ve been together over 2 years now.

I wanted to pay my way, so we go places within my budget and split the bill. Except for Christmas, birthdays and anniversaries. He covers those, someplace nice. And he covers the trips away. I’ll buy us a lunch or drinks during a trip but he covers the rest. He wants to, and I don’t take advantage, and we’re happy. Because the rest of the time, we’re evenly matched.

HoskinsChoice · 21/10/2025 19:09

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!

I am going to go against everyone else. If you are so judgey about people with money, have a complete lack of understanding of wealth and have so little respect for him if you assume he wants fake and botox, you're probably not right for him.

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