Ask The Coach: When Should A Man Pay?

Written by: Love Coach Natalina | Team, Tech & Systems Maven

Love Coach Natalina is a Certified Life & Relationship Coach Who Works With Fellow Adventurers Around The World To Create INSTANT Connection and GET the love they dream of...

September 28, 2019


NZK-2277-L A Recent Letter With A Great Question:

I’m back in the dating game again after a little hiatus, and I’m brushing up on some of (Rori Raye’s) fabulous material!! And there is one topic that I’d love to submit to you..MONEY.It’s a 2-part question:
  1.  When casually dating a man (pre-the exclusivity conversation that he should lead), at what point should a woman offer to pay for something? (My “M.O” is usually on maybe a 4th date, if we’re meeting at the lake for a walk and I’m getting coffee on the way, to also grab him one (small gestures of appreciation), but I’m not sure at what point I should physically pick up a tab for something.
  2. And in follow-up: when exclusively dating a man, do you have any guidance on how paying for things should work? For example, I make a great salary, but when I’m with a man who makes 3x as much as me, and therefore can afford 3 European trips to my one annual trip, do you have any suggestions on how to handle it when he invites me along, but I know the plane ticket is out of my budget? (do just tell him I’d love to go but it isn’t in my budget and then let him pay if he offers, while also being fine with it if he doesn’t?)

The reason I’m asking is that while I’m not uncomfortable being honest about something being out of my budget, or after a few dates chipping in for something small to show appreciation, what I AM concerned about is the balance of letting him be the man vs. making him feel taken advantage of. And, men nowadays – especially in their late 30’s – are SO different where they almost have an expectation that the woman is going to start chipping in immediately, or offer to split the bill. I do NOT date those guys as soon as I realize they are that way, but interacting with so many men like that really does a number on my muscle-memory for when I DO meet a great guy who wants to treat me like a lady. (see the attached image for reference on what it’s like to date in your 30’s nowadays..:)

Do you have any tips on how to mentally balance the payment thing out from your perspective, which is the one that always feels the most correct to me?

From Coach Natalina:

Beautiful Question!

I’m happy to share a few tips that should resonate for the modern woman and the women with old fashioned hearts and souls…so let’s dig in!

The emphasis on wanting to make sure no one feels ‘wronged’ or ‘taken advantage of’ is a great place to start, the energy of this intention often enough will carry it’s weight in gold, but I know you want more than that…

Money issues are still one of the biggest reasons why relationships fail…

Even though views on money have changed, and are changing still, and we are all more progressive with:

– how money is spent
-what it is spent on
-and who is doing the spending …

this territory is still radically diverse with opinions.

In fact! Just today I saw an ad from a reputable credit card company sharing statistics that the average millennial woman feels guilty about many of the purchases she makes, while the average millennial man…. doesn’t. WOAH!

Isn’t that wild?!!

Back to your question  — when casually dating, when should a feminine woman ‘chip in’ ?

my quick answer is, “whenever…” (**with a playful shrug)

because there is no fail-safe formula ‘catch all’ here.

A more detailed cut and dry advice:
“when he asks, and she want to.” The Guideline I stick to and share with most all of my clients is that
it simply feels romantic when a man picks up the bill…

(even when I feel awkward about the gesture, it’s still gets sorted into ‘romantic gestures’) and, this is important because I want to let as many romantic gestures flow in as possible.

I love that you do the coffee sharing, and that is absolutely perfect!

You can extend this to make it your delight to bring enough to share… as opposed to ‘paying him back’ or ‘getting even’.

be willing to feel!

there still isn’t an exact math or science on when and how much to ‘chip in’.

I’m willing to bet that when he’s upset about the arrangment you have together… or If you are feeling uncomfortable…

often enough…WE CAN TELL when our partner is upset…

If you are picking up a sense that he is always the one to pay….and it’s a stress…

would you be willing to have that intimate conversation?

here’s a sample script for a conversation of that nature:

“hey, __________(date’s name), I love our outings together — and I don’t want to put put pressure on you…. like you have to pay every time we go and do anything…. don’t get me wrong…. i find it wildly attractive…what do you think?”

see what he says…!

this is where the awkward can turn into intimacy, are you game for that?

you may be surprised to find that he really does want to pick up the tab

or maybe he tells you directly that he hasn’t been feeling appriciated…

or he may want to take the lead in other ways and hearing verbally from you gives him the green light…

When a woman can feel and receive a man’s gestures of giving…. that may be all he really wants in return.

This has been true for me even with platonic male friends!

so…!!  Stay curious, Babes.

Notice if it’s just your head making up stories about what is ‘right’ and ‘fair’…be willing to feel… and get curious!

this will be interesting for you when the triggers set in, but I promise it’s worth it!

Part 2:

How do you do money when you are more solidly committed and exclusive with a man?

It still feels devastatingly romantic when a man makes an invitation and only wants/needs a, “yes…I’m willing” in order to make arrangements for an ‘Us’.

If you are more of a high powered woman that can flawlessly book a flight, hotel, meals, excursions…. etc…. and ‘keep up’ with him without breaking a sweat or a fingernail…do what feels good.

if that isn’t you… let’s explore that.

say a man, like yours – earning 3x as much as you do, invites you on the kind of trip that you only have in your budget to go one once…once a year…once in a lifetime…

The situation alone will present some wild emotions, in simply receiving the invitation.

…and we haven’t even gotten to any details!

so step one: let’s honor those chaotic feelings first.

how does it feel to get invited to ….. (insert dream trip with dream man here) ?

your mind might immediately get sucked into the ‘how!?’ and ‘…is he going to pay?’ any and all of the mind chatter, and the desire to act…. (or at least I caught myself going there before I even heard the whole invitation… haha… so, nice catch!)

Come back to your breathing, check your gorgeous goddess body for tension, and let yourself melt and soften consciously.

My intention is to savor all of the giving he is doing here…. and his invitation, regardless of how thorough, thought-out and effortless it is for us to say yes… the giving has begun!

(cheering, whistling, hollering and hooting from a stadium crowd)

**i’m curious to know how this piece alone will shift your vibe, and generate connection…

then we choose our words, receive with our whole energy and aura…and then choose the words for the next bit of the dance.

again before diving into the logistics and cutting straight to budget talk, are you willing to respond from the space of how it would feel to go adventuring together around the world?

I hope you said yes…

I hope you said yes to entertaining that bit of romantic bliss.

here’s a sample script for this part:

“a trip with you… like that…. feels ________.”  (feels magical to me. magical…I feel giddy thinking about a trip like that with you….)

And then the real hard core details start to settle in,

“I feel giddy at the idea…it feels magical being asked….what’s the plan…tell me more 🙂 what are you thinking?”

and let him tell you….maybe you will be surprised….

I love your note on not feeling afraid to tell your man something ‘is not in my budget…” and let the chips fall where they may….but I wonder if there is an opportunity for even more connection in these tricky moments.

are you really ‘fine’ if you are invited to do something ridiculously fantasy inducing ?

with the hanging thought that …you can’t or won’t be giving it to yourself…

and you aren’t really sure if this guy is dangling his ‘cool life’ in front of you like a carrot…

(a metaphor for how I am feeling being in the scenario…wow, thank you for telling me about your gorgeous life…. see you later i guess? ) yuck. 🙁

so, explore your options – and keep your heart open – not just being ‘okay’ with various forms of disappointment…

lead with curiosity.

“that feels fun! what’s the plan?!”

let him share, and see how intimate you can share yourself…even when talking plane tickets.

“I feel giddy thinking about going together… can we talk budgeting?”

again — see what he says, you may want to set up another time to talk nitty gritty finances, and there may be some good deal of back-and-forth.

you seem to be a woman who can confidently say, “it feels good to contribute!” financially and otherwise…

“it feels good to contribute…and I feel scared….that I might have to say no …and i’m afraid I’ll feel resentful trying to keep up with you financially….can we talk money?…. what do you think?”

you may be surprised at what happens in a conversation like that, about what you learn about yourself – as well as how many men out there are willing to go deep with you.

I don’t know about being the most correct way or that this way will always feel ‘right’ …but you may find these money decisions do start becoming easier, you may also find the dating pool…fills up….mysteriously… with men who are starving for a woman who will have these types of conversations from the bottom of her soul.


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