This will give you one element for each group:
List<dynamic> data = new List<dynamic>
{
new {ID = 1, Message = "Hello", GroupId = 1, Date = DateTime.Now},
new {ID = 2, Message = "Hello", GroupId = 1, Date = DateTime.Now},
new {ID = 3, Message = "Hey", GroupId = 2, Date = DateTime.Now},
new {ID = 4, Message = "Dude", GroupId = 3, Date = DateTime.Now},
new {ID = 5, Message = "Dude", GroupId = 3, Date = DateTime.Now},
};
var result = data.GroupBy(item => item.GroupId)
.Select(grouping => grouping.FirstOrDefault())
.OrderByDescending(item => item.Date)
.ToList();
var result = data.GroupBy(item => item.GroupId)
.SelectMany(grouping => grouping.Take(1))
.OrderByDescending(item => item.Date)
.ToList();
OrderBy, :
var result = data.GroupBy(item => item.GroupId)
.SelectMany(grouping => grouping.OrderBy(item => item.Date).Take(1))
.OrderByDescending(item => item.Date)
.ToList();