Financial First Date Questions

Given my amazing relationship skills (yes, like my investing, blind luck can be passed off as a skill), I figured I’d help out some folks with a set of useful questions that you can ask on your first date to find out if that person is compatible with you (or not), and has no Financial Skeletons in the Closet. I actually stole the concept from Reddit, but I have put a very financial spin on things, and please add your own questions in the comments, if I miss any good ones.

Rubik's Cube

Some Say Relationships are like a Rubik’s Cube

  1. How many credit cards do you have in your wallet? How many total?
    Note, if the answer is more than 4, run, don’t walk to the exit door
  2. Have you declared bankruptcy in the past 10 years ?
    This might even be a pre-first date question.
  3. How much did that purse cost? -or- How much did that watch cost ?
    If the purse cost more than your monthly rent, you are out with someone who likes the finer things in life (and that is not a compliment).
  4. Do you smoke?
    Any answer other than “no” means higher insurance rates later in life.
  5. Active, Passive or Dividend Investing?
    If the answer is, “I beg  your pardon?”, steeee-rike three!!! Can a dividend investor live happily with an active investor?
  6. Would you rather owe 100 people $10 or 1 person $1000 ?
    Again, there is no correct answer, the correct answer is, “Why would I owe people money?”
  7. When you need cash, do you use a “white” or no-name ATM?
    There is no way you should stay with someone who thinks $3 a withdrawal is OK.
  8. TFSA or RRSP ?
    Again, the answer “What?!?” is an automatic FAIL! However, if they answer TSFA, be on your guard.
  9. How much debt are you currently carrying, and what is your plan to pay it off (if you have debt)?
    If the answer is, “I have no debt”, he or she is a keeper! However, if they say they are carrying $120K in student loans, ask what their profession is, if they are a Dentist, Doctor or some other well-paying professional, then you might be OK, but be wary.

Who said romance is dead? Best to ask these questions so you don’t end up in a Loveless, Sexless Marriage.

Symantec CA


{ 8 comments… add one }
  • Beth May 14, 2015, 7:00 AM

    Too funny! Another red flag: your date is bragging about their stuff. Gentlemen, I’m more likely to be impressed by the size of your TFSA and RRSP, not the size of your truck or hot tub!

    One guy I dated told me before our first date that he’d walk a few extra blocks to get free parking and pay for a good steak at the restaurant. To me, that was someone who was smart enough to not spend on things he didn’t value (parking) and spend on things that do bring him value (a good steak — something that he usually prepares at home.)

    • bigcajunman May 14, 2015, 7:05 AM

      Did he drop you off at the restaurant first? Chivalry is still possible, even if you are trying to be frugal.

  • Barry @ Moneywehave May 13, 2015, 11:20 PM

    No coupons on the first date guys!

    • bigcajunman May 14, 2015, 5:26 AM

      But that would show how frugal you are 🙂

  • aB May 13, 2015, 11:02 AM

    No questions on who’s paying?

    • bigcajunman May 13, 2015, 11:36 AM

      Very true, the infamous,

      “I forgot my wallet, you are OK with paying for this, right?” trick 🙂

  • RICARDO May 13, 2015, 9:50 AM

    All valid questions to find out if the other person, male or female, knows how to manage money and not jsut spend it.
    However if someone asked me these questions on a first date I would be out of there so fast.
    No need to have someone controllng my life – and my money

    • bigcajunman May 13, 2015, 10:00 AM

      Better to get it out of the way first 🙂


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