How To Ask If He's Financially Stable WITHOUT Feeling Super Awkward

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Rarely would someone choose to date a guy who’s more concerned with pinching pennies than enjoying the moment. But dating a beau who lives and breathes the YOLO mantra might potentially lead to fiscal fighting down the road. 

According to this study, 42 percent of men bring debt into a new relationship, while only 29 percent of women do. What kind of debt? The WORST. It’s reported that men, on average, have $4,100 in credit card debt. 

But don’t forget about possible student and car loans. By the time you walk down the aisle, you two could face a serious financial mountain. 

Don’t wait until it’s too late! Determine whether you share the same level of financial responsibility, which will avoid major headache down the road. Here are some red flags to watch for in the early stages of dating:

  • He pulls out all the stops at the mercy of his plastic.
  • He actually uses the YOLO mantra (slightly kidding).
  • Every time you go shopping, you fear the magnetic strip will melt by the end of the "damage" spree.

Just like Goldilocks, you need to find a guy that spends just right.

Too Tight

Your date insists that you walk to the restaurant to save on gas. Halfway there, he insists you and your five-inch heels turn around because he forgot his Groupon code.

Too Loose

The day of your big date, he sends three dozen long-stemmed roses to your office. He picks you up in a nice Benz and pulls out all the stops with fine food, top-shelf liquor and box seats to the playoff game. Unless you know he's loaded and has no financial worries, this should raise concern.

Just Right

You start with a walk in a local park and cool down by sharing a triple scoop vanilla ice cream cone. Later in the afternoon, you end up at a local café. You order some tasty appetizers and cocktails and talk into the night.

A Few Safe Money Questions For Early On In The Relationship

1. Make a probing statement. If he has a nice car (and I mean really nice), it’s fair game to say, “I can’t wait until I make enough to own something like this.” It's a probing statement, and if you have an honest man, he may offer up some details. For example, whether he owns it or leases it or maybe a rough payment amount.

2. Student loan repayment programs? They're a good start. If you know that he went to college, you could ask, “Honestly, in school I never dreamed the payments would be this high on my student loans, did you?” Again, if he's open, he might respond, “Yeah, I'm drowning.” Or, “Actually, I was fortunate enough to have a good paying job during my internship, so it’s almost paid off.”

3. Try to delicately touch on the topic of financial responsibility. “It’s a struggle sometimes not to put things on my credit card. Did you know that the average American household has over $15,000 in credit card debt?” 

Based on his answers, you can get a good sense of what financial behavior he believes in. For example, if he says, “We’re always going to have debt. What's the big deal?" (YIKES. Run!) Or, “My parents taught me to pay cash rather than charge.”

There you go, a simple guide to help you wade through the debtors — I mean, dating pool.

For more advice on how being on the same financial page will strengthen your relationship in the future, visit and fill out the Free Assessment.