For the past several weeks, author Moira Weigel has been on tour for her new book Labor of Love, a bestseller about the history of dating. Her readings are followed by a brief Q&A session; almost always, someone asks her who she thinks should pick up the check on a first date.

Usually, it’s a guy asking if it’s appropriate for him to pay. Other times, it’s an older woman curious whether men still pick up the check these days. “It’s a question people worry about a lot, and I wish I had more direct ‘do this’ kind of answer,” Weigel says.

Even for an expert like her, even in these increasingly progressive times, society still hasn’t reach a consensus about what the etiquette is when the checkbook comes.

What we now call dating is a relatively new practice in the span of human history, according to Weigel. Prior to the 1900s, courtship in America was like something pulled from a Jane Austen novel — a young man would enter a family’s parlor room to call on their daughter, eventually asking for her hand in marriage.

Marriages weren’t arranged, but they were largely transactional. Romantic love played a role in mate selection, but economic factors were much more explicit than they are today. The more a man had to offer financially — land, money, a family business — the more desirable he was (not that that’s not still the case). Conversely, women were considered property by law. Ownership was transferred from father to husband, a tradition we honor by having dads walk their daughters down the aisle to “give them away.”

The term “date” didn’t enter the lexicon until 1896, Weigel says, when it appeared in George Ade’s Chicago Record column “Stories of the Streets and Town.” It was called a date because you put it in your datebook as an after-work appointment.

But it wasn’t until 20 years later, when dating was mentioned in Ladies’ Home Journal, that the practice was deemed socially acceptable for upper-class women. “I always joke that dating was invented in 1896, and by 1916, it’s gone respectable,” Weigel says.

Before that, dating was viewed as akin to prostitution. Single, upper-class women were rarely seen in public before the turn of the 20th century, so when women starting dating, they were often mistaken for working girls. (The term “public woman” was a euphemism for prostitute.)

Economic inequality between men and women only strengthened the association. Men always picked up the tab then, mainly because women were shut out of the workforce and had virtually no earning power. But dating was such a novelty that the act was frequently misperceived as the man actually paying for sex. “Women were actually arrested on prostitution charges for letting men buy them dinner,” Weigel says. (Interestingly, many of the sex workers Weigel interviewed for her book referred to their client appointments as “dates.”)

This gave dating a “prostitution complex,” she says — a hang-up that continues to complicate the economics of straight dating and makes the simple act of picking up the check a fraught experience.

“There are a lot of contrary expectations” regarding who should grab that first check, says Eva Glasrud, a 29-year-old life coach in the Bay Area. Glasrud blames the lack of consensus on our general unease with discussing money.

Splitting it would seem the obvious solution, but even that can foster confusion and worry — many consider splitting the check as an act of public friend-zoning.

“Some women think that if it’s split, it’s not a legitimate romantic date,” Glasrud says. “It puts guys in a tough position between potentially offending somebody [by paying], or sending mixed signals about how much you like somebody or if you even considered it a date.”

Nick Layon — a recently married 30-year-old man in Miami — has a similar view: “The few times I went out with someone and the woman was gracious enough to split the check with me, that was usually an indicator she wasn’t interested.”

Weigel recently had a conversation with a female friend who grew anxious when it came to pay for a first date. The friend was unsure whether the man would pay, and if he didn’t, Was that a signal he wasn’t into her? Would he feel emasculated if she insisted on paying her share?

For others, though, splitting the check is a given. Jordan, a 33-year-old single man in Portland, has been on a dozen first dates this summer alone, and has never felt compelled to pick up the check. “I’m more interested in an equitable relationship where everybody is relatively balanced and one person isn’t looking for support from the other,” he says. He can count on one hand the number of times he picked up the whole check over the past decade, and even then it was always a matter of circumstance, such as the woman forgetting her wallet.

The expectation that men should pay was a function out of our patriarchal past, when men were the sole breadwinners and thus had to prove their ability to provide, Devereaux says. “It was an inherently unequal system, as opposed to now, where people are looking for much broader array of types of relationships.”

Yet Derek Comeau — a pickup artist who uses the moniker “Cajun” and the CEO of Love Systems, a dating consultancy for men looking to attract women — advises all his clients to pay the bill on a first date. It’s not about a man demonstrating his financial prowess, though. “I suggest they say, ‘You can get it next time.’ It cuts through the awkwardness and implies there’s a second date.”

The lack of clarity on this issue has produced what some call the fake purse (or wallet) reach — when the woman grabs for her purse at the end of a date, even though she fully expects the man to pay for the entire meal. It’s both an empty gesture and a test — will the man insist on paying, thus signaling he enjoyed himself on the date, or will he let her follow through on what was intended as a polite but insincere gesture?

Watching someone do a fake reach at a birthday lunch is the closest I'll ever come to know what it's like to go on a first date with a girl — Michelle Markowitz (@michmarkowitz) February 18, 2015

That some women will feign trying to pay in order to appear courteous is a testament to the complexity of the economics of straight dating. Indeed, some men and women can’t even make up their own minds on the matter.

Four years ago, Layon commented on question-and-answer site Quora that a woman would “lose points” if she failed to do the fake purse reach on a date. He said he appreciated gesture, even if he suspected it was feigned. But Layon, who’s since married, says he’s now anti-reach. “It rings hollow. It’s a veneer. It’s saccharine, it’s fake. It wouldn’t sit well with me now.”

Meanwhile, Stella*, a 32-year-old single woman in Boston, says both parties should enter the date expecting to pay their respective shares. That said, “men should offer to pay, not out of chivalry, but because there’s still a difference in the amount of money men and women make,” she says. “It’s not easy squaring those things.”

And this all before factoring in sex.

“There’s always this anxiety [on dates] about what the other person is in it for,” Weigel says. “Are they there because they actually want me, or because they expect something?” Specifically, men worry the woman is just hitting them up for a free meal, and women worry that if they let the man pay, he’ll expect to sleep with them afterward, she explains.

Glasrud says the expectation is real (and problematic) — a function of our instant gratification culture. Technology has socialized men into believing life is a series of checkpoints with defined rewards. You kiss after the first date, go home together after the third.

“Men’s social development isn’t what it used to be, and that’s because they get so much of their entertainment and interaction online,” she says. “But women aren’t algorithms. We’re not a series of ‘if-then’ statements.”

There was one thing everyone agreed on, though: Once a couple gets past the awkward, early dating phase and settles into a committed relationship, they should split it, every time.

The question of who should pay for a date came up in two of Weigel’s Q&A sessions recently.

“In both cases, women in the audience have said, ‘No, most men still do pay.’ One woman was in her 20s, and another was in her 40s, divorced and dating again. “I don’t have rigorous data to support this, but I do think it’s still a norm for men to pay for dates,” Weigel says. But she doesn’t see this as inherently anti-feminist.

“If women paid for their dates more, it wouldn’t change the underlying economic reality [that women earn less than men, on average].” In this way, men paying for dates isn’t patriarchal, it’s an accepted form of “wage redistribution,” she jokes.

Her comments suggest that the only real way to rid ourselves of this angst is to close the pay gap. Any lingering anxiety about who pays for a date “comes very directly out of structural wage inequality,” Weigel says. “And this is something that remains with us in 2016.”