Given this query:
from s in services
select new
{
    s.Id,
    s.DateTime,
    Class = s.Class.Name,
    s.Location,
    s.Price,
    HeadCount = s.Reservations.Sum(r => r.PartySize), // problem here. r.PartySize is int
    s.MaxSeats
}
If the service doesn't have any reservations, this exception is thrown:
System.InvalidOperationException: The cast to value type 'Int32' failed because the materialized value is null. Either the result type's generic parameter or the query must use a nullable type.
I get it, but how should I deal with it? My intention is if there are no reservations, then HeadCount be assigned 0.
There's an even simpler solution:
from s in services
select new
{
    s.Id,
    s.DateTime,
    Class = s.Class.Name,
    s.Location,
    s.Price,
    HeadCount = (int?)s.Reservations.Sum(r => r.PartySize), 
    s.MaxSeats
}
Note the cast. This may also produce simpler SQL than @Ahmad's suggestion.
Essentially, you're just helping out type inference.
You should check for it:
HeadCount = s.Reservations != null ? s.Reservations.Sum(r => r.PartySize) : 0,
                        This should resolve your problem: 
Try to cost the int to int?
from s in services
select new
{
    s.Id,
    s.DateTime,
    Class = s.Class.Name,
    s.Location,
    s.Price,
    HeadCount = s.Reservations.Sum(r => (int?) r.PartySize),
    s.MaxSeats
};
HeadCount = HeadCount ?? 0;
                        A simple ternary operator should fix the problem nicely...
something like this:
HeadCount = (s.Reservations != null && s.Reservations.Any()) ? s.Reservations.Sum(r => r.PartySize) : 0;
This will handle for both null and empty situations
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