Snooze. It's fine, but a bit matey for my liking. I'd rather pay for the whole thing than split it. "I'll get this" is so much smoother than "if I give you this £20... and you give me that £5 and all that change. Then we'll use this other tenner as part of the tip and..." Get lost, you massive bore. Bill-paying time - if there's any discussion about who should pay - weeds out the dickheads. If he says "do you wanna pay because you're like, a feminist, or something" tell him to pay for dinner, then your eye rolling injury surgery and never see him again.
So should one person pay for everything all night?
If someone buys you a whole dinner, don't be a spoilt brat about it - buy a round of cocktails or something. Buy the gig tickets for next time without making it into an issue. You're an adult person with a life. This isn't a Nineties family holiday in Mallorca.
Do you have to sleep with the person who buys you dinner?
If they expect that, they belong in jail.
Does spending a lot of money on you mean they like you more?
No. Giving money emotional value it dangerous game - it's about making the other person feel valued. If it was a business lunch, you wouldn't make your clients pay. If it was a weird scientology centre which you got suckered into by the free street "personality test", then they would provide the biscuits. Value other people, make sure people value you.
Being financially dependable and generous is good but not everything: personality, appearance, beliefs, morals, kindness, funniness, intellect will all come first. Buying dinner is nowhere near the most important thing you can do for someone else but it's a nice thing to do. So, it's fine to let someone buy you dinner but when they do, appreciate it. How? As your mother told you in the beginning, the one simple rule is to always say "thank you".
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