There are only three scenarios: the man pays, the woman pays, or the meal is Dutch, that is, both participants pay their way. On a “traditional” first date, where the man has invited the woman to a meal, he should always pay. Among friends, checks are usually split, or people take turns paying for meals.
• Is there a current rule-of-thumb for who pays on dates? Whoever initiated the event should pay. So, if a woman has asked a man out, she should pay. If a man feels uncomfortable with this, he can reciprocate on a second date.
• If one person wants to pay, what’s the most graceful way to do so to avoid awkwardness? Whoever has asked the other person out should just pick up the check the minute the waiter brings it to the table. It’s that simple.
• I’ve heard it suggested that whoever wants to pay should excuse him/herself for a moment and leave a credit card with the waiter so it’s all taken care of and the check is never sent over. What’s your take on that? This works with business associates, as more than one person often reaches for the bill even though one person did the inviting. In this case, the senior executive should pick up the check. Paying ahead also a good idea for outings with friends when you want to treat the other person or persons.
• What happens when a man never lets a women pay? On a first “traditional” date, the man should always pay. If the dates progress, the woman can offer to chip in with a Sunday brunch or a home-cooked meal. If there is a great disparity in the two people’s incomes, the person who has more money can and probably should pay most of the time, as long as the other person agrees.
• When (if ever) is it okay for a guy to suggest splitting the bill, if his date doesn’t offer outright? There’s nothing wrong with going Dutch, but this should always be proposed and agreed to at the beginning of the meal ahead of time. The awkward part is when the bill comes, and one party does not know this is the case. With group dating, there is an unspoken rule that everyone splits equally.