What Is Really Behind Our Confusion About Who Pays for a Date

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I think we all have a good sense of what it means to look for validation. When we feel that we have done something well or have tried our best, we would like other people to appreciate our efforts. When we are in a work setting or even with family, we seem to be a little better at moderating our expectations and disappointment when we don’t get the validation we expected. However, something seems to happen when this dynamic ensues over the first few dates causing people to erroneously think others are complete jerks when, in reality, the expectations of the dates were not clear from the start.

Who Pays for a Date

Nothing is causing more stress and anxiety than the discussion of who pays for a date. Something that seems so innocuous has always been part of a secret code aimed at figuring out some aspect of a person’s personality. We take the other person’s behavior incredibly personally and we expect to be validated for doing the socially appropriate thing by picking up the check. Our emotional reaction to this question is very much out of balance with the actual behavioral transaction — but why?

Many of my male clients bring up the “who pays” question a lot. My general rule (and the one my grandfather taught me) was “who asks, pays.” It has only been recently that men have started questioning the “fairness” of such a rule. I welcome the discussion as it is one of the single best ways to ascertain what someone’s values around their ideal relationship really is (not what they think it should be).

The problem is that those who hark on the “fairness” issue may also have been those who, that in the past or in a different culture, had expectations that paying for an expensive date meant that there should be an exchange in sexual activity. Fairness in these circumstances definitely is more about a power struggle and entitlement issues than it is about monetary concerns. To avoid these power struggles, young women have resorted to insisting on splitting the check with everyone (regardless if they make significantly less money) in hopes to avoid the expectation that sex is expected. This is seen more often in cultures that have higher rates of rape and domestic violence.

Researchers have recently started to study the phenomenon and have uncovered data to support what we are all experiencing in real life: The “norm” is all over the place and no one really seems happy with any of the solutions. While many men and women still expect men to foot more of the bill at the beginning of dating, 76% of men in this one study felt bad for taking money from a woman yet almost half of them would stop dating her if she never contributed. 44% of women were bothered by men’s expectations that they pay but 40% were bothered when men did not allow them to pay.

It really is a no win situation. Everyone is struggling to make sense of what is the “right” thing to do. Yet, these questions are not new to the LGBTQ community who has learned different ways of defining courtship behaviors from the start. We probably could learn by asking out LGBTQ friends their views on how to navigate these situations and understand why the commitment to equality is important (not simply based on a fear mindset).

Who Pays Outside of the United States

This issue is not only affecting dating dynamics in the United States but abroad as well. My experiences in Argentina has introduced me to many men who have grown exhausted over trying to figure out which women want to split the check (and still go on a second date) and which women who expect to follow the common rule of “who asks, pays.” In the past two weeks alone, I’ve had this conversation at least ten times. All ten times the men seemed generally interested in learning how to be better about navigating this issue without feeling like they are constantly offending people. Men in Argentina claim that the Feminist movement has caused them a lot of stress and provided little answers on how best to move forward. As a result, many of them default to splitting the check even if it makes them feel very uncomfortable doing so.

To me, this is not what feminism is about. Feminism is about giving people the right to choose how one would like to be treated. It means that there should be open conversations around issues related to dating and money. It means we get to design the rules that work best for each one of us. Unfortunately, few men feel that the conversation is happening in an open and supportive manner. The result is a lot of unnecessary shame and a feeling of wanting to avoid dating altogether.

Suggestions for Navigating the “Who Pays” Scenario

Communication will become more and more necessary. We can no longer assume that someone understands our dating preferences since there are no rigid rules any longer. My suggestion is for the person who is taking the lead to simply ask prior to the date, “I would like to be respectful of your preferences — what are your views on who pays the check?” This should not launch into a debate but should just give the other person the opportunity to express any concerns before agreeing to the date. If all else fails, the “who asks, pays” rule can navigate sticky situations by simply saying to the other person, “I really enjoyed my time with you. I asked you. Let me get this one.” It leaves room for the other person to reciprocate in the future. If the date insists, do not assume splitting the check is code for being “friend-zoned.” Old rules may not apply and if you are interested in a second date, simply ask and see what happens.

If you were asked on an initial date from a dating app, one other option if you are worried about navigating this scenario, is to show up early and buy your own coffee or glass of wine/cocktail. Such a meeting should not last more than 90 minutes and will give you an idea as to how you would like to handle this situation with this person in the future. It takes the discussion off the table completely for an initial meeting which may help you relax and be fully present.

A date is an opportunity to meet someone and see if you can not only have fun together but whether there is potential for some kind of relationship. Our job on a date is not to get our own needs met but to be the best possible date we can be for the other person. As such, being a grownup who picks up the check without much concern about keeping track of the details will always be attractive. We still do this behavior in business for a reason. Generosity is never a bad way to go but we all have to be respectful where someone else is coming from. The insistence on splitting the check may come from a fear of sexual violence based on the culture you are living in, not based on something you did personally.

Why Our Deep Discomfort with Receiving Needs to Be Resolved

The other issue that needs to be resolved is our deep issues with receptive energy. We are all very much trained to try to be the giver when, in reality, we all need more practice on receiving the generosity of others. So many of us rob our dates of the joy of giving that it is little wonder why fewer people are reporting having sexual chemistry with people. Real intimacy requires real comfort with not only giving but receiving. Someone paying for your date should cause the same amount of joy that paying for that date brings. It is a gift to allow the space for someone to step in and have the honor of treating you. I’m sure you do this all the time. It is appropriate for you to find balance within yourself of giving and receiving. Being comfortable with receiving is a very powerful life tool that few of us truly master. It is the embodiment of gratitude and more of us need to practice embracing this in the context of connecting with other people. It is not giving up your power. On the contrary, being comfortable with receiving and expressing gratitude puts you in a far more powerful position to negotiate the future of your courtship.

Why Knowing Who You Are is Necessary

We can no longer show up on a date and wing the situation without some very awkward consequences. We have to know what our ideal relationship looks like and our preferences when we are dating. Then we need to be comfortable in our role. Confusion is much more likely to happen if you believe you are a more “traditional” dater but then insist on splitting the check (or vice versa). If you are constantly having trouble with the issue of who pays on a date, the issue may be in your screening process of who is a good fit for you. If you cannot own what it is you want and be the person you really are, you will end up in a multitude of awkward situations with the wrong people.

And perhaps that is what is really going on — we are dating the wrong people because we don’t know what we want and who we really are.

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