class Foo(models.Model):
    ...

class UserFoo(models.Model):
    user = models.ForeignKey(User)
    foo = models.ForeignKey(Foo)
    ...

    class Meta:
        unique_together = ("user", "foo")

foos = Foo.objects.raw("SELECT foo.* FROM foo LEFT OUTER JOIN userfoo ON (foo.id = userfoo.foo_id AND foo.user_id = %s)", [request.user.id])

def userfoo_retriever(qs):
    userfoos = dict((i.pk, i) for i in UserFoo.objects.filter(foo__in=qs))
    for i in qs:
        i.userfoo = userfoos.get(i.pk, None)

for foo in Foo.objects.filter(…).tranform(userfoo_retriever):
    print foo.userfoo