Something like this perhaps?

--DDL and some data:

create table Dates (

UserID int not null,

InDate date not null,

Weeks int not null);

insert into Dates (UserID,InDate, Weeks)

select 1,'8/31/2012',5 union

select 2,'9/14/2012',2;

--Expected results:

--UserID,OutDates

--1,9/7/2012

--1,9/14/2012

--1,9/21/2012

--1,9/28/2012

--1,10/5/2012

--2,9/21/2012

--2,9/28/2012

with cteTally(n) as (

select top (select max(d1.Weeks) from Dates d1)

row_number() over (order by (select null)) as n

from

sys.all_columns a

cross join sys.all_columns b

)

select

d.UserID,

dateadd(wk, t.n, d.InDate) OutDates

from

Dates d

cross join cteTally t

where

t.n <= d.Weeks

order by

d.UserID,

OutDates

;

go

drop table Dates;

go