How would you handle a dinner bill under these circumstances?

[Anonymous]

I am going out of my way to where this woman lives, instead of the place we had talked about before.. which is actually more like 2/3rds from me (but it's NYC) ... so I am going to her town instead. She will pick the restaurant because she knows the area and I don't.. She's older than me.. I don't know her money situation, but if she sold her house she'd probably net 7 figures from the sale (really expensive town)... so do I offer to pay the bill, or agree if she wants to split it or pay for it? I am not hurting for money, but yeah.. Also before that I'd probably suggest we continue the date maybe in private, I dunno... depending on how she responds to that would also impact how I handle it.

[MrOracle]

You should not invite anyone to a date that you aren't happily prepared to pay for yourself. But, really, this starts even before that.

You should not plan a date that involves costs that you aren't happy to pay. Why would you invite what is apparently a stranger to a dinner date, especially one that could be expensive? in my opinion, dinner dates are for women you are already in a relationship with and have vetted - early dates should be focused on talking with each other and should be kept at a minimal cost. Maybe you meet for ice cream, and walk around the city, or something along those lines, so that you can talk. Maybe you sit down in a café and get coffee. But you keep the costs down so that, should it not work out, the monetary cost is negligible.

in my opinion, it sounds like you are trying to "lead with your wallet" - impressing her with what you can pay for by taking her out to dinner. That's a big mistake. Your priorities should be to vet her morals, values, personality, and attitude, and let her do the same for you. If you lead with your wallet, she's just going to see you as a wallet.

And, yes, maybe she wouldn't have accepted a coffee or ice cream date. That's good to know up-front, because that also reveals her morals and values. If that were to happen, that's a WIN for you, not a loss. A loss is taking a stranger woman to an expensive dinner date and spending several hundred bucks potentially only for things to go nowhere.

[shades777]

Yea expensive dinner dates never turned out good for me, the cheaper the date the luckier I was

[Asker]

what are you talking about? It would be a restaurant she’s picking. And she had more money than I do. She’s a millionaire based on the value of her house alone plus whatever she has. I’ve never spent hundreds of dollars on dinner. Although when I spent like 130 something dollars on it and the girl turned out to be nasty I insisted she pay for her half. I had to get her to PayPal it to me so it was annoying but yea.. she also picked the place.

[MrOracle]

So... your own experience is that a dinner date for a stranger became a hassle, but you didn't learn from that? Why not avoid that hassle, at least until you've vetted her enough to know that you aren't likely to have that kind of problem?

YOU asked the question, and how much money she has is irrelevant. Also, why is SHE picking the restaurant? You're the man, you should be making the decisions. Do you not understand that most women are turned off when they have to make the decisions? Most women would rather go somewhere that was their 27th choice rather than be the one to pick even if that meant going to their first choice - and most of the exceptions are just gold-diggers who just want to maximize how much of your money they can get.

[MisterWack]

I’d say upfront via message before the date starts what my plan of payment method is. Personally I would go for paying for my bill and she pays for her bill though it is up to the individual to find out what works for them.

You are allowed to say you are running low on cash (don’t have to explain why) and be weary by not paying since she would appreciate the honesty, transparency, and the financial saving too at least that is how it should be. If my girlfriend was running low on money I’d understand, I don't know just my thought I guess.

[Account]

This always puzzles me and I only see it online. Why are people overthinking it? I am always inclined to pay no matter what.
Why do people think about it so much? It makes me think that they value money too much. Me and my friends always get into fights over who is going to treat the other. Same when I dated my exes. Sometimes I paid and sometimes they paid.
Why are some people so stingy to the point of overthinking about such stuff? LMAO.

[pierre7i]

Great response @Account -- agree with everything you say !

[Alwayreckles93]

Why not invited her to church or a church gathering? Personally me as a woman first I would make sure the guys is a believer and if he can actually memorize his Bible scriptures. Believers must never date unbelievers! First do your research check if she's Christian!

[Asker]

I assume you’re married with a kid? I thought I would find somebody years ago. I’m not gonna wait forever.

[Alwayreckles93]

Yes I am married to my wonderful Christian husband he also happens to be a pastor. Ok but what exactly do you know about this woman? Does she read her Bible everyday? Does she go to church each and every Sunday? Is she Christian? Does she volunteer at her church? See this question are very important to ask her. If she's Catholic then that is deal breaker for you. Catholic woman are wild demonic and crazy. Just make sure she's Christian that's all I must say.

[Alwayreckles93]

Does this woman celebrate Halloween? If she does BLOCK HER! Have you tough about joining a Christian dating app or have you try going to a Christian church for Christian singles gatherings?

[AviatorTom]

If you suggested going out to dinner, then you should offer to pay for dinner for the two of you.

[Asker]

she was not gonna be able to meet me until after six. What do you expect us to do at that time?

[Anonymous]

That you even think about the possibility of her paying for you sounds really ungallant tbh, if not a little bit self-entitled !

You should offer to pay, if she declines, as she almost certainly would, then simply split the bill 50/50 - easy, fair and surely affordable, right?

If by saying you'll probably suggest you continue the date in private you're telling her straight away you want to have sex with her?

Hmmm, first date you're expecting that? She may think you're the universe's gift to women of course, but what if she says 'no' ? !

[IridescentWave]

My rule is whoever invited pays. If I invite, I pay. If they invite, I expect them to pay. If they suggest going 50/50, then I oblige; but I'm less likely to accept later invites. Also, what happens after the date never factors into consideration of who pays for the meal.

[Staximus]

Stop being a cheapskate bum and just pay the goddamned bill. Don't be an idiot and "suggest we continue the date maybe in private" unless she said made it clear that she wants to have sex. You stated that how you handle the bill will depend on whether or not she wants to "continue the date in private", which is a shitbag move and you need to learn how to act like a gentleman and not like a fucking shit bag.

[pierre7i]

Brilliant @Staximus ! Everything you said is absolutely right !!

[Staximus]

@pierre7i this bozo thinks he's every woman's dream and is doing her a favor or something, like his dick isn't replaceable.

[pierre7i]

Agree with you - cheapskate, self-entitled and definitely ungallant !

[jshm2]

Relax, take the date and have a good time, but don't drink, and keep your wits about you.

If she's game, then pay the full bill. If she's not, then split the bill, and wish her a good night.

[Ez-Bri-Z_v2]

Just split the bill so you don't have expectations of more being required (like continuing in private) just because you paid.

[Anonymous]

That is up to you, this is always personal and sets how a relationship will work. For me as a woman I always asked to pay my share. It is how I was raised.

[Abbycado]

I always assume I am splitting if that helps.

[exitseven]

The problem with dating is that you have to invest in a relationship. I have gone through worse.

[NewWaves]

Hold up. What do you intend on doing if she doesn't want to continue in private?

[Anonymous]

And this is why I'd never let a man pay for a date

[Anonymous]

I don’t like the last sentence, makes her feel like a prostitute, but under the circumstances I think splitting the bill sounds reasonable.

[JamesRandiDebates]

First dates are Starbuck's for coffee followed by a BJ in the car. Dinners don't start until after full sex.

[Anonymous]

If you get there and she's hot, pay the bill, if not split it.

[Peridot25]

Ew! Is that how you treat human beings? That’s disgusting.

[Unit1]

@Peridot25 ew indeed. For once i agree with you there.

[KrakenAttackin]

NYC women... good luck bro.

[Asker]

she lives in Rye. So very well to do town.

[KrakenAttackin]

She will expect quite a bit from you.

[LiamJHayden]

Discuss it beforehand.

[Anonymous]

Just pay outright, that's the way it should be

[Anonymous]

What do you mean by in private?