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For many women, they find it more comfortable to reach for a check than to have an awkward conversation. Wallets at the ready, chaps. Like drinks at happy hour.

If someone suggests the Eiffel Tower restaurant they should stump up for the airfare and meal and pick somewhere less tacky. Regardless of your feelings on the matter, whatever you do, don't leave the house without enough money to pay for at least your share.

First Dates: Who Should Pay…and Why

I remember one time a former boss of mine kept persuading me to go to a Thai restaurant with him. He kept saying it was so amazing and that I should go. I just wanted to get fast food so that I could work on my work without taking like an entire hour away from it. Yet he kept insisting and so I reluctantly went to Thai restaurant with him. After we ate the waiter asked about the bill and he said to split the bill. I was taken back since I thought, for sure, he'd pay in this case. Unfortunately I didn't have enough cash so I offered to pay with the credit card. The waiter said they can't accept a credit card. Meanwhile the boss is watching me and still not doing anything. So they told me there was an ATM at a gas station across the street, so I cross the street, withdraw some cash, come back, and pay for the bill. And at that point I thought my boss was such a cheapskate. If I relate it to the work analogy, if a colleague of mine asks to hang out for drinks after work, he might be the one asking but we're colleagues; we're mutually hanging out; no one is leading and no one is following. And in that case I'd expect to split the bill. But when the boss asks, then that's a very different dynamic. He's taking the reigns. He's leading in that case, and we're following. Even if the leader asks for suggestions, he always makes the executive decision in that scenario.

When one solo's flush and the other's not, the person with the bigger bank account should do more of the treating. And you do that by talking. This means she has to feel protected and safe in his company—both from outside forces—and from him. If I had to pay or go halves, that would put me off a man. Dating stage 3: Fifth dates and afterwards After the fourth or fifth date, you should be comfortable enough to take it in turns to pay for each date. On our way to a local bookstore to sit on the terrace with vodka and a few magazines, this guy let out a.