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Who Pays On The First Date, Who Doesn't & Why

It’s still the norm that the vast majority of women are free loaders. They rarely offer to pay their fair share. Last week this woman I met suggested a fancy restaurant and insisted on making us a reservation. When the check arrived, I put my $70 down and told her that it was $70 each. She said she had no money and left for the bathroom as she now suddenly had an emergency. She is an executive at Disney, but like the vast majority of women, go to great lengths to con a man into paying for everything. Even when a man refuses they usually come with the “I have no money on me” con job.

I'm not sure how many dates preceded this night. I'm assuming this was a first date. Regardless, you were in no way obligated to go to the restaurant she chose. You chose to go along with her request. You always had the ability to Google this venue to get a sense of the pricing of its offerings. If you felt the place was too expensive, you had the agency to speak up and suggest a different location for your date. Instead, you went along with the request knowing she was probably expecting you to pay. In a nutshell, you set this woman up to fail, and fail she did.

It's not that most women are con artists waiting to bleed an unsuspecting man dry. It's that you - subconsciously or otherwise - put yourself in situations for this behavior to unfold. This is a classic example of confirmation bias. You believe women are freeloaders. You enter into a scenario you know in advance will probably leave you feeling used. As predicted, you do and you blame the woman when you are equally to blame. Was she wrong for choosing fancy place then expecting you to pay? Absolutely. That kind of entitlement is boorish and unacceptable. Were you wrong for sitting back and waiting for her to fulfill your prophecy so you could continue believing all women are grifters? You bet. The minute you decided to acquiesce, you waived your right to complain.

If the goal is to avoid this scenario, here are a few things to remember:

When it comes to planning a date, let the person presumed (but not expected) to be paying to select the venue. That's simple etiquette. Therefore, this woman was out of line for choosing to go to a place she knew was expensive. That said...

You pick, you pay. - If you're the one who wants to go an upscale bar or pricey restaurant, plan on paying the tab. Again, this is basic etiquette.

If your date is with someone you met online, you're both on the hook for the bill. - Ever wonder why some people take FOREVER to suggest an offline date? Sometimes, it's because they know if they do the onus will be on them to pay. You're both on that dating site to get dates. When you're chatting, it's assumed there's mutual interest. In this context, it's not fair to stand on principle and expect the one asking to pay.

If your date tells you to pick a spot, be reasonable. - Sometimes, a request like this is a test. If the person chooses a high-end venue, the date is mysteriously canceled OR the saga depicted above occurs. Find a place that is centrally located between both of you that is moderately priced. Then, tell them the name of the place you found so they can Google it and determine if its within their budget.

Always plan to pay your half. - This woman's lame excuse of not having money on her isn't just flimsy, it's impossible. Nobody leaves their home without a debit or credit card. She excused herself to go to the bathroom hoping he'd pay the bill before she got back. I don't know what adult needs to be told never to buy anything they can't afford to pay cash for in that moment. That includes dates.

Never upgrade the date. - A drinks date is just that. It's not open to interpretation. Again, follow the lead of the person presumed to be paying the tab. If they suggest food and you're hungry, by all means order something, but nothing too extravagant.

Never assume what they can afford because of their profession, where they live, etc. - It's not your place to determine someone else's financial situation. You don't know what they're dealing with behind the scenes. If it's "just" a cup of coffee or "just" a glass of wine, then you shouldn't mind paying for it.

If your date suggests another round or to order food and you're not interested in seeing them, politely say no. - If you know you're not interested in having another date, don't take advantage. Conversely...

If you suggest another cocktail or appetizer and they decline, read the room. - This is the universal cue for "I'm not feeling it." They're telling you in an indirect way they don't wish to prolong the date and want to leave.

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