Dating: Does The Guy Always Have To Pay For The Date Or Should The Bill Be Split

Should you split the bill? This story about saying what you mean when paying or splitting the bill makes me sad. Is it only worrywarts who experience recurring snapshots from the distant past that still make them sad?
Years ago, my parents went to dinner with the parents of my close friend. My mom and dad were of modest means and Close Friend’s parents owned Impressionist paintings. At the end of dinner, my father — ever the gentleman — offered to pick up the tab for the whole dinner. My friend’s father, a most charming and quirky man, said OK and thanks.

My mother told me this story, with a tsk-tsk undertone. My friend’s mother was also tsk-tsking. On the one hand, I can’t hold it against my friend’s father, because I know what a direct guy he was, one who always said what he meant and expected others to do the same. (I myself am so literal that when someone tells a joke, I think it really happened that a priest, a rabbi and a minister were in a bar… “No kidding!” I say.)

On the other hand, I would have expected human understanding to have kicked in and that Friend’s Father would have offered at least to split the cost of dinner. All this raises the general question: Should you split the bill? I nearly always offer to pay more if I order more; at Hank’s Oyster Bar, my favorite D.C. eating place, I become non-negotiable about paying for my indulgences when I can’t decide between the lobster roll dinner and the fried clams dinner, so I order both. At coffee with a friend, I simply cannot abide the “I’ll pay, you can pay next time” approach. It’s the kind of thing I would run home and put on my week-at-a-glance iCal and have to keep forwarding to remind myself. If I think a coffee or dinner mate is not rich enough to benefit from tax breaks for the wealthy (as for me, I can afford name-brand running shoes and organic kibbles for my beagle), I try to tip the pay scale my way.

On the other hand, when I’m with someone who owns an airplane, I might offer to pay half, but I don’t argue if he reaches for the bill with authority. A 60-year-old woman friend of mine insists on splitting the bill, especially on a first date. Otherwise, she feels beholden and obligated to go on a second date, even if she doesn’t want to, so that she can pay. As for younger singles, I found this comment on the Internet: If a guy agrees to split the bill on the first date, he is unlikely to ever have a second date. But if she isn’t chipping in by the third date, that is a sign she is a taker and not a giver. No man wants to date a taker. When going out in a group, some young people drink Coke, others imbibe multiple beers; some order a salad, others a steak.

Often, those in their teens and twenties need to spend prudently. One suggestion when anticipating an imbalance is to bring cash (preferably in small denominations) and, as soon as the bill comes, put your share on the table; be sure to include tax and tip (roughly 20 to 25% of your tab). Alternatively, invite your parents along and let them pay.

How do you deal with splitting the bill?