Poll: Who Should Pay For Dinner On A First Date? By YourTango. Posted on Nov 9th 2008. EmailPrint Comment? Picking up the check etiquette. On a first date, does the feminist in you insist on going dutch or are you happy to have him pay? Sound in. Poll: Who Should Pay For Dinner On A First Date?: He should. Have all the perks gone out of dating? I should. It sets a bad tone for the relationship if I let him pick up the check. It depends on who asks who. The peson who initiates the date pays. Both of us. It's the 21st century!