Linq query with nullable sum

You want to use the nullable form of Sum, so try casting your value to a nullable:

from i in Db.Items
select new VotedItem
{
    ItemId = i.ItemId,
    Points = (from v in Db.Votes
              where b.ItemId == v.ItemId
              select v.Points).Sum(r => (decimal?) r.Points)
}

Your issue is discussed here in more detail:

http://weblogs.asp.net/zeeshanhirani/archive/2008/07/15/applying-aggregates-to-empty-collections-causes-exception-in-linq-to-sql.aspx