I'm assuming I'm getting this error because I'm reading the same CSV twice (I don't fully understand why this is an issue tho) but I need the code below to do the following 2 things...

1) Give me a the total count of all the rows in the CSV.

2) Give me the first two lines only of the data for me to display back to the user.

file = upload.filepath
#I READ THE FILE
file_read = csv.reader(file)

#GET THE COUNT I.E. 100 ROWS
row_count = sum(1 for row in file_read)

#ADD TO DATA JUST THE FIRST TWO ROWS THAT I WILL USE TO DISPLAY BACK TO THE USER
data = []
for i in range(2):
    data.append(file_read.next())

How can I achieve this?

Why not reverse the two statements? You can read the first two lines in using your:

#ADD TO DATA JUST THE FIRST TWO ROWS THAT I WILL USE TO DISPLAY BACK TO THE USER
data = []
for i in range(2):
    data.append(file_read.next())

Then do the row count for the remaining rows, and add 2:

#GET THE COUNT I.E. 100 ROWS
row_count = 2 + sum(1 for row in file_read)

However, will give incorrect results if you have <2 rows. A better solution may be to simply read in the whole file, then count the rows in the resulting list.

import csv

# Open the file upload.filepath, get a pointer in file
# file automatically closed at end of 'with' context
with open(upload.filepath, 'r') as file:

    #I READ THE FILE
    file_read = csv.reader(file)

    data = []
    for row in file_read:
        data.append(row)

    rows = len(data)
    first_two_rows = data[:2]

If it's a massive file, and your worried about memory, you can add a count variable, and only append to data when its <=2

data = []
rows = 0
for row in file_read:
    rows += 1
    if rows<3:
        data.append(row)