Top 10 Awkward Money Scenarios to Avoid on a First Date

That first date can be stressful enough — imagine if an awkward money situation arises on top of all the other things you’re worried could go wrong. Even a great date can go downhill quickly if someone makes a financial faux pas.

The key is to be prepared for any scenario so you can respond appropriately. Here are 10 awkward money moments that can happen — and dating advice on how to handle them with grace and ease.

couple, couples, dating, first date


Your Date Forgets His Wallet

Imagine going on a first date with someone who says he forgot his wallet when the check comes. Talk about embarrassing — for both of you. This actually happened to “The Recovering Spender” author Lauren Greutman, who blogs about frugal living at

She and her date were in their 20s and in college. “After we were done eating, he went to pull out his debit card to pay and realized he had left his wallet at home,” Greutman said. “I thankfully had my wallet with me, so I paid.” She didn’t think much of that awkward first date and gave him another chance. Now they’re married with four kids.

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