Dating Dilemma: Who Picks Up The Tab?

Dating Dilemma: Who Picks Up The Tab?

For Valentine’s Day, we asked LearnVest readers the question: Who pays on a date? It was a close tie between: “After date one, split the bill or take turns” and “I’m kind of still old fashioned; I’d rather the man pay.” Interestingly enough, not many of you think income level should come into play.


Image of Who Should Pay Poll ResultsNonetheless, times were simpler when men made all the money and nontraditional couples were few and far between. In an age of higher earnings for women and online dating—in which nothing is traditional—it’s tempting to land on the side of “who the hell knows nowadays?” (which, as a matter of fact, got 16%).

Dates 3 to 10: Murky Waters.

Most agree that whoever does the inviting is the one who should pay—this often means that the guy pays the first few times. Of course, the dynamic is fuzzier with same-sex couples, or once the pair passes beyond the initial threshold but hasn’t yet entered into couple territory. One of our friends offered to pay on the third date, the guy accepted her offer, and from then on every time the bill came, there was an awkward silence. She didn't want him to stop treating, but they've been splitting the bill ever since, and it has dampened her enthusiasm.

What's the solution? We suggest a little role-playing and surprise.

Money doesn't have to become an awkward accounting between two people dating; it can be an opportunity to show your affection in unique and fun ways. We're not a fan of splitting bills because it can feel unromantic. Alternating who pays can work, but it often evokes keeping track, and it's awkward if one person makes a lot less than the other (Jean Georges one night and McDonald's the next?).

Here are three solutions we propose, which work just as well in dating or relationships (if you are dating, it may be more unspoken):

1. Role Play.

One of our friend's boyfriends makes about six times as much as she does. But never opening your wallet may make the guy feel unappreciated, and the girl feel like a kept woman. They decided to be “cab girl” and "dinner guy.” The roles are clear, and both are contributing to the costs whenever they go out. This cute system works beyond the dating stage into couplehood as well. Other ways you could split:

  • Concert tickets --- gas
  • Babysitting costs --- an evening out
  • Groceries for a home-cooked meal --- dinners out
  • Airline tickets --- the rest of the vacation

There are a lot of creative ways to think about this, and contributions can be sensitive to what you each make.

2. Frequency Trumps Amount.

The point is to show that both of you are invested and appreciate the other person, not to keep score. So, think frequency rather than amount. It makes a positive impact if both parties are contributing on a regular basis--thoughtful gestures like picking up his favorite donuts, getting the popcorn at the movies, or tipping the bellman can go far in making the dating dynamic feel more natural and like there's a two-way flow.

3. Mix It Up.

Don't fall into rote habits or roles with your financial contributions to the relationship. Keep things interesting (it goes for life as well as money). After he's treated you to an indulgent dinner, swing by a bodega to pick up his favorite clove cigarettes, or by the deli to grab the Ben & Jerry's for later. Surprise her with the latest issue of her favorite newsstand magazine. Spontaneity and thoughtfulness will go far in keeping the relationship out of a (financial or otherwise) rut.

The Bottom Line.

Don’t think he doesn’t care about you just because he lets you pay your way—the men we spoke with were very chivalrous but said they take a woman's offer to pay somewhat seriously, believing the woman wants to assert her financial independence. If you feel like he should pay, let him--instead of the "faux reach" (which you'd better be willing to follow through on without resentment if you make it!), find other small ways to thank him or contribute.

Everyone's trying to figure out what the rules are, men and women. If you find yourself staring awkwardly at the bill once too often, don’t be afraid to have a conversation about it--just keep it light and appropriate for that stage of dating. (The prenup talk can wait.)


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