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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:
TwistedWonder · 21/10/2025 18:44

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 making assumptions and pre judging him
based on nothing.

Go on the date - it’s one evening of your life.

You never know you might actually enjoy it.

NameChangeForThisQuestionOnly · 21/10/2025 18:44

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?!?!

Don’t make judgements about him based on his job or how much money you think he has. Judge him on how he treats you on the date, how he speaks to you, whether you have chemistry.

Arlanymor · 21/10/2025 18:42

Why do you feel inferior? I think that's something you need to get to grips with if you intend on using OLD because it is not a place for the faint hearted. I would rip the bandaid off and just go - what's the worst that can happen? You have a middle-of-the-road date, a nice meal and then call it a day?

CheeseSandwich1 · 21/10/2025 18:41

Whatsthatsheila · 21/10/2025 18:38

why do you feel inferior?

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?!?!

OP posts:
NameChangeForThisQuestionOnly · 21/10/2025 18:41

Why do you feel inferior? Just go, it’s his treat, he offered, go and enjoy it. There’s no obligation for it to become anything other than a nice night out.

MrsMoastyToasty · 21/10/2025 18:40

Fake it until you make it.

blackrabbitwhiterabbit · 21/10/2025 18:39

Just go!

Whatsthatsheila · 21/10/2025 18:38

why do you feel inferior?