Feeling bad that her relationship with Dean (recurring guest star JARED PADALECKI) has become awkward, Lorelai suggests that she and Luke go on a double date with Rory and Dean. But Lorelai's plans go awry when Luke is unable to disguise the fact that he thinks Dean isn't good enough for Rory. Meanwhile, Emily and Richard are lonely and a little lost without each other, but neither one can take the first step towards reconciliation.