Money Questions to ask on a date 

May is Money Month

May is money month! We’ve had 4 months of recovering from 2022 and now is the time to focus. And what better way than through reviewing and refreshing those early date questions you love to pull out? No more questions on favourite colours and animals. Dates 2-5 are about digging a little deeper. 

This is part of a series of money questions one needs to ask when first dating someone. Money is one of the main reasons couples break up and the reasons vary from overspending, under  earning, risks etc. People don’t often realise until it’s too late how important a shared approach to money is.

Money Questions aren’t easy as many are private so be cautious and don’t grill the other person. One must be prepared to share details about your own money situation without sounding like you’re on the poverty line or bragging. It’s a tricky balance.. Talk about what’s important to you financially as well. E.g. security or experiences? 

Disclaimer: Most people either lie or lack self awareness so don’t take what they say or write to you as gospel. It’s more their attitude and values that are important to you as opposed to what they have to share. Assume they will share nothing with you whilst dating. Sorry if gifts is your love language. Cozzie Livs means that everyone is less generous with the 


Assets can be tricky as nobody wants to be deemed a gold digger. It’s important to know how much someone has accumulated in assets. This matters less in your 20s when you are both in that first few jobs stage of life but post 35 this is something that one would assume that someone has semi sorted. The etiquette rule here is that you want someone who has similar or more than you in assets but not significantly more that you feel uncomfortable.  This is trickier in;

a) certain circles where women are earning more than men;

b) with the wage gap where certain industries and positions have ethnic and gender pay gaps; 

c) where there are dependents e.g.children or in some cultures family (Black Tax is real oh!); 

d) there is inherited assets 

e) there has been a recent division of assets e.g. divorce / breakup and; 

f) there is a significant age gap between the two.

One can’t assume anything about these assets but they are the basis for understanding the other person’s financial base. Also these assets may not actually belong to the person fully. These could either be in trust or be part of a company or be shared assets with family so, again, ask don’t assume. Another common one is shared ownership. A bugger to get out of. 

Assets Examples

An example is that I don’t own a car. It’s a depreciating asset and I don’t understand men who are into cars. But it’s a car. Asking details on why that car, the pros and cons of leasing vs. buying gives me an insight into how he thinks. I have an ex who loves both expensive and classic cars. He leases them on the weekend, showing off and luring in women who are impressed by cars. He was broke!

Another is that I have a mortgage so I don’t really have to navigate the London rental market. However I am aware that Parisiens and New Yorkers are fans of renting so Londoners are a bit of an anomaly. Someone not owning isn’t that surprising in these times but this would depend on age. Younger people are less into ownership. 

So be clear on what matters to you and why. You don’t want to be one of those people who use dating as a financial leg up but at the same time you don’t want to be with someone who is on the brink of bankruptcy either. 


So you meet him and it sounds like he has a solid job. But they have an ex in the Home Counties with 2-3 children in private or boarding school. These are not cheap to maintain especially if supporting more than one household. Alimony is a huge burden sometimes and can leave people having to work paycheque to paycheque.  

So if they are divorced you need to find out how they co parent and if they have enough disposable income to date in the way you want to date. No point planning that Maldives trip if they’re more RyanAir to somewhere in Spain kinda person.

Alimony is a sensitive issue and can bring some bitterness or anger so be sensitive when asking about this and understanding. Maybe why they’re not suggesting fancy eateries on early dates. 

We’ll move onto the Bs later in the week (including Bills and bankruptcy) but until then, welcome to Money May! Happy Dating!

© Chelsea Black ® 2023

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