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How to Avoid “Who Pays for the Bill?” Dating Anxiety While Increasing Emotional Connection on Dates: A practical approach to money and dating that is equal parts feminist, realist and idealist.

1 Heart it! Regina Fletcher 224
July 5, 2018
Regina Fletcher
1 Heart it! 224

“I’m suggesting you take a short break from online dating, maybe one month to six weeks.”

I’ll never forget the look of horror and panic I saw on my client face at hearing this suggestion.

“But, that feels like I’m doing nothing. I mean, all my friends are meeting their partners online. I’m almost 35!”

I took a deep breath and remembered the difference between teaching state mandated curriculum in public school and coaching adults with disposable income who pay me at will.

“Ok. How about a compromise: no proactive work with dating apps. You can respond to people who send you messages, but only if there is a compelling message or indicator in their profile. No browsing, no swiping. We’ll try for one month.”

Tears welled up, she took a deep breath and said, “Ok, I’ll try. Just one month”

I went home and calculated the financial impact of losing this client, and revised my Yelp profile. The next week I saw her, and she reported that she was at the type of Jewish professionals party where she typically already knows half the people, when she met a gem, a few months out of a long distance relationship, with whom she had unmistakable chemistry. It was a while before they would go on the kind of date that involved splitting a bill. Instead they traded long, heartfelt, text messages, and eventually realized that the timing of their relationship was off. Never again did my client settle for a guilt-ridden high end first and last dinner date.

It is seeing this transformation from having unfulfilling consumption-oriented dates to finding romance in connection-heavy environments, that I have come to champion the non-bill splitting “date” (you’ll later see why I put the term in quotes).

As a relationship coach who advocates both for the personal relationship success of my clients, and as an activist who advocates for a more equitable world in which excessive consumption is decreased, I often get into this bind: How do I advise my clients to create the relationships they desire, when the easiest, sometimes most effective, dating techniques perpetuate gender inequality and excessive consumption?

I want to tell my hetero male clients to assume that the women they date are their financial equals and that it’s very respectful to assume they will split the bill, and yet I know that when men don’t offer to pay for the bill, many women are turned off. Many of those women are self-proclaimed feminists with the most acrobatic explanation for why male strangers should treat them to meals. This has led me to rethink the way I advocate for my clients and the more equitable, fun world many of us want to live in.

A bit of housekeeping before we begin: I refer to common dynamics in hetero romantic relationships, but with a little flexibility, you can apply these principles to genderfluid or LGBTQI romantic or sexual connection as well.

So how exactly do you date without bill-splitting?

I’m going to be honest, and start by telling you that my answers involve patience, intentionally slowing down and welcoming ambiguity. If you are firmly attached to planting three Tinder dates into your jam-packed week, you can stop reading right now. If you can’t tolerate the thought of getting into situations in which you think “Wait, is this a date or not?” these techniques will not work for you. If you find spending a couple hours getting to know an interesting human being with whom you eventually decide you have no romantic future is a waste of time, then these techniques will waste your time.

However, if you are frustrated with how much time, money and energy you put into thinking about how to manage and pay for your dates with strangers, read on!

Let me start with a few assumptions I make so we can get on the same page:


Assumption #1: Traditional Hetero Dating Involves Men Leading Women

The act of a man offering to pay for a first dinner date is rarely the only instance of male leadership in a dating context. So often the same women who expect men to pay for a first date, also expect him to express more clear enthusiasm for a second date, and initiate romantic or sexual interest.

I find this to be a dysfunctional tradition, because much of society agrees that women are more intuitive, have been groomed more to navigating social cues, and are more likely to face sexual harassment. All the above reasons would point to women (or people who embody feminine energy) being the much better suited gender for taking the lead in the world of navigating new relationships. From what my clients share with me, I notice that the assumption that men will take leadership in dating leads to confusion and inaccurate assumptions. I often counsel women I work with to know that if they don’t make their interest in someone clear after a first date, someone else with less attachment to traditional gender roles will do so before them.


Assumption #2: The Tradition of Men Leading Women in Dating Stems From a History of Men Leading Important Decision Making (and this doesn’t mean that men who like to pay for women are bad)

We all know that much of Western history has included women being barred from owning property, voting and having the financial means to make their own decisions. While the dynamic of masculine energy being rooted in providing and protecting can be very admirable and nourishing, paying for a date doesn’t actually demonstrate providing very much. Charging a fancy dinner to your credit card does not demonstrate being a provider more than texting you will be five minutes late because you last minute volunteered to drop your nephew off at soccer practice because his mom got sick. The current expectation that men should pay for dates comes from the expectation that men have been in positions of financial and political dominance over women. There are much better ways to demonstrate your ability to be generous or to be a provider.


Assumption #3: Stress About Bill Paying Causes Unnecessary Emotional and Financial Strain

You are probably reading this article because you are anxious or annoyed at how much space this issue occupies in your life or your bank account. You’re probably more interested in figuring out how to quickly get into interesting conversation topics, how to show affection in ways that are well-received, and how to choose people who are aligned with your values.


Men of diverse financial means share their woes about dating with me. High-income earning men share how used they feel when several first dates in a row don’t even offer to share the bill. This often leads to bitterness about dating and suspicion of future dates. Even though it’s a drop in the bucket of their bank accounts, it creates a ripple effects in their overall attitude about dating and their likability. Men of limited financial means tell me about the bind they find themselves in. Does it make sense to spend your limited disposable income on people you don’t yet know, especially at the cost not of spending money with friends and family who have already demonstrated years of loyalty and love?


Are we still on the same page about how this tradition can be harmful? Ok, the truth is, I have let men pay for me on dates and I know it can work well for many people, but I never go on “dates” with people until we have already established a reasonable assumption of ongoing interest.


How do I do this? Here are some of my techniques:


Technique #1: Put yourself in situations that are likely to generate interesting new connections with people you might want to date.

You know how some of your friends met their partners in school, at work, through friends, and didn’t actually go on “dates” until they had known each other for months? Part of the reason those relationships go so smoothly is that by the time they found themselves at an expensive dinner, they knew a little bit about one another’s financial situation, and they genuinely knew that there was enough rapport for one person to truly get joy from paying for the other person.

“But I already know my friend’s friends, I can’t date at work and I’m not in school! That’s why I’m swiping right so much!” Don’t worry! I hear you. By intentionally talking to new people at parties, enrolling in interesting classes or going to interactive workshops you can start to expand the amount of people you connect with in contexts where people are supposed to be having rewarding or enjoyable interactions. Remember, you still need to make the first move and initiate socializing outside of the group context (a.k.a “asking them out”) regardless of your gender because you cannot assume that anyone at these events are reading your mind.


Technique #2: Invite people to non-date like activities before you get into a bill splitting situation.

This one works best when you know enough about someone to realize you have a shared passion or interest. It is possible to do this with dating apps, but with little space given to personal descriptions on many of the apps, it can be tricky. Here are some examples of how I quickly transition into an activity that doesn’t involve bill splitting.


“I saw you like art. Want to check out some (free) art galleries?”


“You said you do yoga. I’m already going to a talk on Yoga in the West. Do you want to see if there are still tickets left and join me?”


“You said you like dogs. Want to volunteer at this animal shelter event in a couple weeks?”


All of the above invitations will put you in free or low-cost environments that give you opportunities to connect without paying for a bill. After spending a few hours doing one of the above activities, it will probably feel natural and authentic for one person to say “Let me get lunch! I was really inspired by how you volunteered to clean up dog poop even though you were assigned to guest check in. It would bring me so much happiness to treat you to lunch.”


Technique #3: Give authentic, personal reasons for your preference around how to handle paying for activities


As I said, I have let men pay for me before even I though I believe this gesture stems from a history of male financial dominance, but there is always a warm, sometimes playful explanation for how we manage this. Here’s how some of these conversations go:


“Please, in my culture/generation it feels really sweet to treat someone someone to dinner, when you are getting to know them.  Would you mind if I got this bill this time?”


“I have had wonderful time with you and I’d like to make plans for the future. As a principled feminist, it really means a lot to me to split the bill equally. Would you mind if we split the bill?”


“Look, I know you are very busy raising kids on your own/doing an undervalued service-oriented job. I really appreciate you taking one of your only free Saturdays with me. It only feels right for me to treat you. Would that be ok?”


“I don’t know what to expect at this new-agey woo, woo event I invited you to. Honestly, I don’t know if you’re going to even like it, so could I treat you to the tickets?”

All of these techniques involve being more personalized and vulnerable in your connections with people, and I know that can be scary. If you aren’t used to interacting in these ways, it might be useful to go to workshops, work with a relationship professional or see a therapist to help you become more confident and comfortable with yourself. While these techniques are slower than matching with dozens of dating app profiles, you’ll spend less time and money with people you don’t end up connecting with, and the money and time you do spend will be more aligned with your values.


Once you have adjusted your framework about dating to include non-bill splitting activities, and you have practiced voicing your financial and social truth, you’ll be navigating bill paying with so much grace that you’ll be thinking more about getting to know the person you’re spending time with than figuring out how to handle the bill.


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1 Heart it! Regina Fletcher 224
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