Tom had to
Тому надо было придерживаться правил.
Tom should have followed the rules.
Tom should have said yes.
Тому надо было ещё на пару часов остаться.
Tom should have stayed for another couple of hours.
Тому надо было обнять Мэри.
Tom should have hugged Mary.
Tom should have gone with you.
Tom should have arrived earlier.
Tom should have asked.
Тому надо было быть адвокатом.
Tom should have been a lawyer.
Тому надо было меня подождать.
Tom had to wait for me.
Tom should have stayed.