Out of curiosity, I started thinking about how people bring up money conversations while dating. The topic actually came up during catch-up seshs with my friends, and honestly—I was shooketh. A few of them are settling down with their partners, and apparently... they never really had the money talk. Or if they do, it's just above the surface talk.
For me, at least in theory, it’s something I’d definitely want to discuss especially before making long-term commitments. But I also get it. Talking about money can feel awkward. I’ve been on dates where people brought it up in roundabout ways, and I wasn’t always sure how to respond.
Here are some questions I asked ChatGPT:
1) If you’re on a blind date, do you think the conversation of money (whether as direct as earnings/debt or spending habits) should be brought up?
Great question. On a blind date, diving too deep into money topics—like exact earnings or debt—can come off a bit intense unless the conversation naturally leans that way. But bringing up money values? Totally fair game.
Stuff like:
- "I prefer experiences over things"
- "I’m pretty frugal unless it’s on travel or food"
- "I’m trying to hit some financial goals this year"
—these can reveal a lot about someone without making it awkward.
If both people vibe well and the convo flows, then more direct money talk (like budgeting styles, views on debt, or FIRE) might organically come up in future dates. But first date? Keep it casual, curious, and lightly insightful.
In the Head Over Heels Podcast in one of the episode titled 50/50 In a Relationship?, Mr Money’s response within minute 16:06 - 17:18. To quote, rather than asking directly how much a person is making, to do a simple calculation on their lifestyle by asking about their spending habits and assessing how they respond to it.
This, I think is a great idea! Tho again, when a relationship progress, I still expect more monies-related conversations.
2) I have been on dates where the guys tries to assess my money habits indirectly and I find that annoying? Personally I’d rather they be direct.
Totally fair—and honestly, that makes a lot of sense. The indirect probing can feel sneaky or patronizing, like they’re trying to test you instead of just having an honest conversation. It’s way more respectful (and refreshing) when someone’s upfront: “I care a lot about financial compatibility—mind if I ask how you feel about saving or spending?”
And it’s cool that you’d prefer directness. It signals confidence and emotional maturity on both sides. Money is a big part of relationships; why tiptoe around it like it’s taboo?
3) I have been on dates where the guys either or for real indirectly flaunt their simple lifestyle (ie say they have no money). I think it’s their way of saying, I don’t want a gold digger and all. I’ve heard one list down stuff like, “the shoes RM11, singlets RM10, etc.”.
I didn’t know what to say but showed him the unsuspecting branded bag (my first’s) I brought that day LOL. Why do you think guys do this? What’s the proper reaction? How would you use this to get into money conversation?
Guys who do that often think they’re being strategic—like, subtly testing to see if you’re “materialistic” or if your values align with theirs. But it can come off as insecure, performative, or like they’ve been burned before. Flaunting simplicity is still… flaunting. And the irony? It can feel as off-putting as flaunting wealth.
Why they do it:
- Preemptive defense: They’re guarding against being “used” for money.
- Signal of values: Trying to communicate frugality, minimalism, or FIRE goals.
- Social test: Want to see how you react—will you get uncomfortable, brag back, or dismiss them?
Proper reaction?
Depends on the vibe, but something like: “That’s cool you know your priorities. I like nice things, but I’m intentional with money—I don’t buy stuff just to impress.”
That keeps it open and invites a real convo without letting them assume anything.
How to pivot into a better money convo:
You could say:
- “Sounds like you’re pretty conscious about spending—is that a personal philosophy or more from experience?”
- “Do you follow a budget, or just naturally spend less?”
Or even playful:
- “RM11 shoes? That’s impressive detective work—what do you splurge on, if anything?”
That way, you flip the script: now you’re curious about them, and it opens the door to deeper values chat—debt, FIRE, investing, lifestyle goals—all without making it an interview.
4) While I would be put off by display of branded stuff from a guy, I wouldn’t go for overly cheap guys. What’s your take on this?
That’s a totally reasonable stance, and honestly, I think a lot of people feel the same way but don’t always know how to articulate it.
Branded peacocking can feel shallow, like they’re using stuff to mask a lack of depth or trying to buy admiration. But on the flip side, guys who are too cheap—where every decision is about saving the next RM2—can come across as rigid, anxious, or even stingy with other forms of generosity, not just money.
It’s really about balance, right?
Attractive:
- Intentional spending
- Financial awareness
- Generosity without expectation
- Knows when to save, when to enjoy
Unattractive:
- Obsessive frugality that turns into control
- Bragging (whether about riches or thriftiness)
- Expecting others to conform to their money habits
Your take makes sense: it’s not about how much they spend, but how they value things. If they spend thoughtfully, show confidence in their choices, and aren’t trying to make you pass hidden “tests”—that’s way more appealing than either extreme.
While here I say “flaunting branded stuff”, I also meant flaunting wealth too much. As in show off-ish lah. For myself, a guy with too much ego is too tiring to handle.
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