Dealing with Dinner Tab Dilemmas

Back in the day, a man asked a woman out. When they went out, he paid for the date. Then women’s lib happened and women asked men out and they paid for the date. The 1990’s happened, and women asked men out and still expected the man to pay for a date. Okay, so now that there are all these sticky situations in the dating world: who pays for what?

Sticky Situation 1: A man asks a woman out to dinner. If a man asks a woman out to dinner and he should pay. Call me old-fashioned, but if you ask someone out, you should pay for the meal. Here is how I get out of this situation. When the bill comes, ask what your side is, a true gentleman will tell you not to worry about it and he’ll appreciate the fact that you at least offered. It’s like extra brownie points. If he tells you what you owe him for dinner, pay for it. If it’s the first date, don’t go out with him again.

Sticky Situation 2: A woman asks a man out.Technically, you ask him out, it should be the exact same situation as situation number one. You ask, you pay. If he grabs the check, you can tell him it’s not necessary, if he doesn’t, you asked anyway, it should be a no-brainer.

Sticky Situation 3: It’s your third date and he’s been doing the asking. Around this time, a woman might feel inclined to pick up the check, especially if he’s paid for everything up until this point. At the very least, around this time if you haven’t done so already, you should at least offer to pick up your half or the whole thing. If he lets you, it shouldn’t be a big deal at this point.

Sticky Situation 4: More than one activity date.If you are really concerned about money, divide up what is spent and by who. If you go to a movie, one pays for the tickets and the other pays for the food (food unfortunately is expensive enough that it works out to be just about even).

Sticky Situation 5: One activity is really expensive. So you go to a sporting event, a play, or do something really lavish, now what? If you are really concerned by this, pay for your half. Going dutch can never go wrong. If you feel really obligated to contribute, go to a nice dinner and foot the bill. The next time you get tickets to something, take your boyfriend.

Sticky Situation 6: You go on vacation. All right I’m at a loss for this one. Vacations depend on several things. First, what is the event? Is it your anniversary or V-day? Or is it a business function and he gets to take a date? The differences are very vast, but either way, people feel obliged to do something in return. Of course, if you are at the point in your relationship where you are going on vacations together, you should feel comfortable enough to ask if there is anything you can pay for. If there isn’t, bring a nice bottle of wine or get him a present at the hotel like a massage on you. (Or you can massage him yourself, wink.)

Sticky Situation 7: You’ve been dating for a while. Like going out with your best friend, I have a philosophy, it all evens out in the end. One pays for dinner here, the other pays for lunch there. I buy your coffee, you buy my soda. It’s just a higher form of going dutch. Nine times out of ten, this equation works out all right.

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