Four years ago, fresh out of law school, Blessing Akinsilo was excited about her first real date in years. She had drinks with her match at a bar in Los Angeles, and the conversation felt easy. Things were going well — until he asked what she did for work.

They started guessing each other’s salary. He was an aspiring actor juggling part-time gigs. She was working in entertainment law. When her date assumed she was making more money than he was, she laughed and admitted that she had six figures of student loan debt.

His face twisted in surprise. Ten minutes later, they were splitting the check and saying awkward goodbyes. She never heard from him again.

Months later, Ms. Akinsilo and a man she had matched with on the dating app Hinge were messaging and joking about student loans. She figured it was safe to tell him how much she owed on her loan, thinking he would relate. But when he learned that her level of debt dwarfed his — he owed a quarter of what she did — the messages dried up fast.

They never made it to a first date.

“I wish I could go back in time and tell myself, ‘Don’t bring up these student loans and other things,’” said Ms. Akinsilo, now 31 and still navigating the dating scene.

For generations, couples have danced around conversations involving money in the early stage of a relationship. Whether out of discomfort, fear of being judged or simply not knowing when or how to bring it up, many people avoid talking about how much they earn, how much they owe or how they like to spend their money. More Americans feel comfortable discussing politics or religion than conversing about their finances, according to a 2024 Bankrate report.