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The Awkward-Proof Guide to Handling the Check on a First Date

How to Handle the Check on a First Date Without Making It Awkward

Nothing can disrupt the mood on a first date more than the bill being dropped on your table. Sure, the cocktails were killer with the conversation flowing freely, but just like that, the air shifts. It’s a stiff standoff as you and your date both awkwardly fumble for your wallets.

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Perhaps they reach for their card with no intention of actually paying, forcing you to repeatedly insist that you’d like to treat. Or perhaps you assumed you’d go dutch, but your date isn’t even attempting to contribute. There are lots of potential misunderstandings that can happen when the check comes, but luckily, it’s totally possible to avoid them altogether.

According to a recent survey of 300,000 single Americans, a whopping two-thirds (63 percent) of guys think that the man should pay on a first date. However, less than half of women (46 percent) agree. And while nearly one in five women prefers going dutch, less than one in 10 men are down to split the bill evenly. Sounds troublesome, right?

In reality, handling the check doesn’t have to be such a conundrum. The key is to go into the date with a specific intention, set that expectation ahead of time and stick to your guns. As for after the first date … well, then it gets a little more complicated — but we’ve got you covered. Below, we’ll go over how to handle the bill at every stage of your relationship.

How to Handle the Check on the First Date

According to etiquette and relationship expert April Masini, figuring out who should pay actually has nothing to do with gender. If you’re looking for a rule you can stick to that will simplify things, she’s got one.

“Whoever does the asking should do the paying,” she says. “In other words, if you ask someone out on a date, the polite thing to do is to treat them.”

Basically, if it was your idea to grab drinks or hit up that new restaurant, the gracious thing would be to cover the bill on your dime. That said, there’s still a chance that your date will try to contribute when the check comes. In order to minimize any potential awkwardness, Masini recommends being very clear about your invitation from the get-go.

For example, you might say “Let me buy you dinner,” or “Let me take you out, I’d love to treat you.” That way, your date can relax when the check comes as you’ve already made things clear ahead of time.

On the other hand, if you’re the one who was invited on the date and you feel uneasy about letting the other person pay, Masini suggests offering to cover the tab if/when you decide to go out again.

How to Handle the Check on the Third Date

Once you’ve gone out a few times, the dynamic may shift a bit. If one person initially paid the bill, the other person may decide to pick up some of the slack. But there are a few factors at play here: who did the inviting, like before, and who’s in a financial position to treat.

“If you both make similar amounts of money, then you can start alternating who pays for dates,” says Masini. “This should happen organically and casually. For instance, the person who has not been paying may pick up tickets to a concert and invite the other person. Or they may invite the other person for a home-cooked meal that they shop for and prepare.”

While some couples may opt to go dutch, Masini notes that it’s less romantic than switching off who pays the check.

“It doesn’t create a feeling of taking care of one another, which is a nice part of relationships,” she explains.

How to Handle the Check Once You’ve Started a Relationship

By the time you’re in a committed relationship, the status quo changes again. Very often, as that initial courting stage ends, both people in the relationship expect each other to pull their own weight. This is especially true once you move in together, blending your finances together as one.

“You both know more about how much you each make, save and spend,” says Masini, “and it’s easier to know who can afford to treat, and how you want to handle money as a couple. If you’re living together, you don’t just have dates to think about — you have to think about paying rent or mortgage and who pays what, who’s on title or on the lease and how you save and spend separately and together. By the time you’re living together, who pays for dates is a much smaller blip on the radar, and it’s dwarfed by who pays for groceries and how you’re saving for vacations and retirement together.”

Of course, income still comes into play when deciding who will foot the bill on dates. According to Masini, if there’s a significant difference in how much both partners are earning, the person who has the vastly higher income should pay for a larger portion of the dates as the relationship progresses. That being said, there are ways for the partner who earns less to contribute financially in their own way.

For example, if the higher earner picks up dinner on date night, the other partner can grab breakfast (or just coffee) the next morning. It’s important to note that it’s always better to openly discuss this kind of financial understanding than it is to make assumptions. While it may feel awkward to bring up who’s paying for what, it’s the only way to ensure you’re both on the same page, thus preventing the kind of misunderstandings that breed resentment or lead to conflict.

And any perceived awkwardness around the bill typically stems from your internal anxieties or beliefs.

“It’s often carried over from the way money was handled or taught growing up,” notes Masini. “If you expect to pay for a date because you invited someone out to dinner, then there’s no awkwardness. And if you expect to be treated to dinner because someone invited you, there is no awkwardness.”

Paying for a date is a very personal thing, and the status quo will vary from couple to couple, depending on their personalities, preferences, incomes, and other factors.

“In some cases, it’s more important to one person — regardless of whether they have more or less money than a partner — to do the paying because it makes them feel more capable and chivalrous,” adds Masini.

In other words, there is no perfect rule or formula for figuring out who should pay on a date. Generally, if you invite someone out, it’s a good idea to cover the costs — at least in the very beginning of the relationship. But when in doubt, talk it out. Once your relationship begins to progress, your dynamic will undoubtedly change, explaining why constant communication is key. The best part? Having these tough money talks early on will only make your relationship stronger (and will help keep from spoiling your dinner).

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