Shepherd's pie is a rich, warming dish that pairs nicely with a traditional dessert.  So, yes, you should serve a dessert with shepherd's pie. Some good options include a scoop of ice cream, apple crumble, or a tart.  You can also make the classic English trifle, which is made with layers of custard, cake, and fruit. Other desserts that pair well with shepherd's pie are berry cobbler, brownies, or even a simple bowl of fresh fruit.