Taboo topic of the week: money in dating and relationships

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Money is not the most pleasant topic to discuss in mainstream western culture. Sally Draper (Mad Men) asks her mom: “Are we rich?” Betty Draper (Sally’s mom) says, “It is very impolite to talk about money.” Clearly, many individuals find it uncomfortable while talking about money. Yet in a romantic relationship, money is probably the most paramount topic – I know this doesn’t sound romantic at all.

  • Do not be afraid to discuss personal finances in dating & relationships.

When you believe that money is an awkward topic, it becomes even more awkward. But when you are completely relaxed while mentioning this topic, your girlfriend will feel less awkward – you are a team!

However, when both of you find it too awkward to talk about money, it only means you two are not a team. Here is why:

  • If you are a team, you would trust each other.
  • If you are not a team, you avoid talking about money but you can’t stop thinking about money or worrying about personal finances. That’s exactly how manipulation arises in many romantic relationships.

So, from now on, I’d like you to have this new mindset: it’s perfectly okay to discuss money with your girlfriend as a real relationship should be best characterized by honesty. In the long run, you’ll have less stress and drama if both of you are on the same page in terms of money. That is to say, because you discuss difficult topics early in this romantic relationship, your love life will become easier to manage in the long term.

Tim Ferriss famously said, “Easy decisions, hard life. Hard decisions, easy life.” I couldn’t agree more!money love

  • How to talk about money in dating and relationships:

Speaking of serious topics, most people do not like surprises. Therefore, if you assume you are dating a rich woman but she turns out to be a bum or a basic bitch, you will be very surprised or even shocked.

Thus, it’s crucial to know your girlfriend’s personal finances early in the relationship.

Here is the million-dollar question: How should you talk about money in dating &romantic relationships?

As you are looking at someone’s online dating profile, you may estimate this individual’s income according to her lifestyle in her profile photos. But the first impression is oftentimes NOT the last impression in dating! This is very sad, but very true.

Nevertheless, in most superficial relationships, the first impression is the last impression as well. For example, when a new employee gets the employer’s approval during the job interview, the first impression may be the last impression as expectations in the workplace are not too hard to meet. No one will think too much in professional relationships.

Yet if you plan to marry a woman, it’s a totally different situation. Basically, the first impression is not the last impression in a romantic in dating and relationships

Never be fooled by the first impression that a woman has given you. A lot of people can’t wait to display their luxurious lifestyle on their dating profiles; however, how many of them are actually wealthy? Usually, a truly rich person wants to be low-profile, whereas many bums want to show off!

So, if you think you are dating a rich lady, you must find out these two things very early in the relationship: 1) Where does she live? If she lives in an affluent neighborhood, her wealth is more likely to be real. Although you don’t really have to know her exact address, at least you can ask which area she lives. 2) Where does she work? If she is the CEO of a wildly successful business, chances are she is seriously rich.

That’s how you evaluate a woman’s wealth without directly talking about money in online date

  • How to test if a rich sugar momma is for real:

When you are dating a sugar momma who is keen to have a dinner date with you, you can say this to her, “Why don’t we fly to Hawaii for a romantic date? We can go to XYZ restaurant there and join a concert. Today I can book the flight on your card.

If this sugar momma is for real, your suggestion will be fine so long as she has the time to do something spontaneous.

I understand that not everybody is a con artist who pretends to be affluent so as to get something from other people. There are lots of high-value women who are single, wealthy and very generous. Therefore, it’s normal to talk about money in dating when you know money is not an issue for your sugar momma.

  • Trust is the prerequisite of talking about money in dating and relationships.

The less you avoid a difficult topic, the easier your conversation with a woman will get.

This is a list of key questions that you may ask your girlfriend:

  1. What is your Money Dial?” (A Money Dial: something that you do not mind spending lots of money on, i.e. things you highly value.)
  2. What’s your money management routine?” (Some people have a money timeby themselves every week, e.g. every Monday they sit down and check their money.)
  3. What’s your money goal?” (Some individuals plan to save $100,000 in 3 years; some individuals plan to make $100,000 every year.)

In order to help you talk about money in dating with ease, I’d like to give you another strategy: you would be well-advised to use “we”, “us” & “our” more frequently in conversations so that your girlfriend will feel closer to you women date


  1. Every fortnight we should have a money time so we may look at our personal finances together.”
  2. We’ll need to have a monthly budget so that we can have a better financial future.”
  3. Should we open a shared bank account?”

Yes, talking about money in dating doesn’t have to be difficult.

  • A typical single woman’s reality in this day and age:

I know a woman who is artistic, creative, intelligent, wealthy and attractive. More importantly, she is single and that’s her choice.

This woman is a freelancer who works from home. She teaches some English programs online and writes several columns for newspapers & magazines. When she was young, her dream was to become Carrie Bradshaw, and now she is living her dreams in Miami!

She isn’t seriously rich and certainly is not a sugar momma. But she is financially free – she has her own property, her own business & she doesn’t lack money. What’s more, she manages her own timetable and has a lot of freedom.

A woman like that doesn’t care whether she has a partner or not because she is very secure and happy.

“When I am old, I will sell my house and go to the nursing home,” says this lady, “Right now I only want to enjoy life!”


 Talking about money in dating and relationships isn’t the easiest thing in the world, but it is a super important topic!

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