A young friend of mine, Max, recently complained to me that his now ex-girlfriend of 3.5 months never paid when they went out. He resented it, yet as a self-described feminist he didn’t want to impose his expectations on her. She could have shared expenses, but chose not to. Respecting her choice, he violated his own by paying full freight.

Listening to Max describe this no-win situation, my first thought was that he backed himself into a corner by overthinking the situation. Why not just say something and clear the air? If she doesn’t like it, maybe she’s not the right one for him. (As it turned out, she wasn’t.)

But, upon reflection, it occurred to me that Max and his generation are caught in the crosshairs of slow-to-change social norms and rapidly changing expectations, which affect dating and relationships, household formation and finances.

When reality doesn’t match expectations, things can get complicated. Today most young men and women expect to share the cost of a date, yet men still feel pressured to pay, while women are happy to let them. Today women expect to marry their equal, but college educated professional women now outnumber “qualified” men. Today young people expect to equally share home and work responsibilities, yet women, who often out earn their partners, still bare the brunt of domestic duty, especially when kids are involved.

Something isn’t adding up. In spite of their strong belief in gender equality, Max and his generation naturally default to traditional sex roles. No wonder he’s befuddled.

When it comes to dating there is no simple solution. Men typically pick up the check on the first date and continue to pay because they don’t want to be seen as cheap. Even though most young women don’t mind chipping in, they tend to reinforce traditional dating behavior by measuring a man’s interest through payment. If he doesn’t pay, she feels he’s not interested. If he does, he’s a nice guy and chivalrous. (Ironically, while she sees him as chivalrous, he doesn’t want to appear chauvinistic by denying her the opportunity to pay her share.)

So when it comes to paying for dating, how can millennials find the right balance between their modern views and traditional tendencies? Some just take a practical approach:

• Alternate who pays.

• The one who asks pays.

• The one who makes more pays more.

No matter what approach you take, it all boils down to communication. Discuss who’s going to pay for what. If you can’t have this conversation, you’re not with the right person, as Max now knows.