Dear Helena,
I go on a lot of first dates on, and it’s getting really expensive. If I see a woman more than once, she usually offers to pay on the second date, but if there’s no second date, it doesn’t seem fair that I should pay for the first date. It’s not as if I asked her out—it was a mutually agreed upon thing that happened through email. Must I, as the guy, always be the one who pays for the first date? Why can’t we split the tab?
—Buy Your Own Drink

Dear Buy Your Own Drink,
Like it or not, most women expect that the man will pay for the first date, be it drinks, dinner, or both. Failing to treat is usually a deal-breaker—far worse than having garlic breath or neurotic dietary restrictions. All the hetero women I talked to said as much, regardless of how much money they make or how strong their belief in sexual equality. Feel free to stand up for men’s rights by splitting the tab. But know that you then risk letting somebody you might otherwise have had a great relationship with slip through your fingers.

The woman should offer to pay her share on a first date, but this is merely a gesture. Jane Coloccia, who works in marketing and public relations, went on about 200 Internet dates over a period of eight years. The man nearly always paid, she says. Only the stingiest accepted her offer to split the check. “One time I went out to a bar with a guy and I had an iced tea. He had a couple of beers and a bunch of apps, and at the end he said, ‘Your half is …'” Needless to say, there was no second date. (Using a coupon on a first date isn’t kosher either.)

The expectation that he pay can be pretty hard on the man’s wallet, especially now that online dating makes dozens of first dates possible. Mark*, an experienced online dater in San Francisco, says: “If I’m going on a couple of dates a week, that adds up. Even if we just go for drinks, that’s $20 or $25 per date.” He’s pretty frustrated with the situation. “The idea that the man should always pay the first time is kind of like [men buying] engagement rings. If the genders were reversed, the custom would have ended a long time ago.”

Without extensive research, it’s impossible to generalize about gay and lesbian dating mores. My survey of lesbian friends suggested that there is no clear etiquette on who pays for the first date in the lesbian world, though respondents wished there were. But a gay source stated that men should split the bill on a first date. This is ideal. Though in general I don’t recommend check-splitting, it makes sense on first dates, where being treated can lead to an uneasy sense of obligation. Plus, when you treat a friend, you know he’ll treat you in turn next time. On first dates, you never know if you’re going to see the other person again.

But what if you are certain that you don’t want a second date? It’s bad enough that you wasted two hours listening to some stranger tell you stories about her cat, why should you shell out for artisanal cocktails too? Samantha Daniels, founder of Samantha’s Table, a professional matchmaking service, says that selective treating could backfire though. “Pick and choose which women you pay for and you’ll end up with a bad reputation. Maybe you don’t want to pay for Amanda, but then three weeks later you meet her best friend who you might really like, but Amanda might tell her: ‘You don’t want to date that guy, he’s cheap.'”

*He did not wish his real name to be used.

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