WTF Friday: Should her date subsidize her babysitter costs?

I’ve been having a blast dating and have met lots of nice guys, many of whom turn into second dates and beyond. The problem comes when the dinner or bar bill arrives. I expect them to pick up the tab since I am usually paying for a sitter while I’m out (which I let them know), and I can tell that ticks them off. If the guy is a single dad, we go out on one of the many nights his kids are with their moms, or if they don’t have kids, I feel they have far more disposable income and should pick up the tab. Many of them feel differently.

What do you think?

Going broke in Bushwick, Brooklyn

Dear Broke,

We don’t live in communist Cuba where resources are (supposedly) distributed among the masses. We live in the hotbed of capitalism where single moms may or may not qualify for state support and the poor are getting poorer and the rich are destroying the environment and moving good jobs overseas and laughing all the way to the bank. Politics aside, the rule is: You have kids, you pay for them. Here’s why:

1. That’s just the rule.

2. None of us knows what another’s financial situation truly is. Even if you know a person’s income, how many kids he has and what his home is worth, any number of other factors could be at play: debt, support of an elderly parent, a spendy sex addiction, etc. It’s a first date. You’re not going to get all the details yet. Don’t assume he has more than you.

3. Make a good first impression. I have struggled to reconcile my feminism with my gut feeling that guys should pick up the tab on a first date — a conundrum I explored in this story. The bottom line: It’s good to get relationships off on the right foot; guys feel like men when they pay; but any many man worth sitting through a second round of Negra Modelos will appreciate you make “the reach” — a lame yet requisite attempt to pick up the bill with the assumption that he will insist. Otherwise, you come across as entitled and/or a gold-digger.

Now, here’s the exception: You become involved, everyone gets a rough sense of the other party’s financial situation and you just work it out. My last boyfriend and I eventually found ourselves more or less taking turns because when we sussed up each other’s finances, our incomes and expenses were probably about equal. But he won a soft spot in my heart when — several months into dating — he instituted the rule that any time I was paying for a sitter while we were out, the dinner was on him.