“An optimist is a person who has no trouble seeing the bright side of your problems” was printed in the Green Bay (WI) Press-Gazette on June 25, 1983, by American humor columnist Doug Larson (1926-2017). The same saying appeared in Larson’s columns on September 24, 1999, and on January 12, 2000.
   
“Milton Berle used to say that an optimist is a man who always sees the bright side of YOUR problem” was printed in the book I’m the Other Man in My Own Marriage!: A Frustrating and Funny Look at Family Living (2000) by Howard Noel. “An optimist is someone who always sees the bright side of your problem” is another form of the saying, but there is no evidence that American comedian and actor Milton Berle (1908-2002) ever said it.
   
 
Wikipedia: Doug Larson
Doug Larson (February 10, 1926 to April 1, 2017) was a columnist and editor for the Door County Advocate (1953–1964) and wrote a daily column, “Doug’s Dugout,” for the Green Bay Press-Gazette (1964–1988), both Wisconsin-based newspapers. The column was originally syndicated through United Media under the title “Senator Soaper Says”; Larson took over authorship in 1980. Previously, it had been written by Bill Vaughn of the Kansas City Star. Larson was born in Sturgeon Bay, Wisconsin.
 
25 June 1983, Green Bay (WI) Press-Gazette, Doug Larson column, pg. A-15, col. 5:
An optimist is a person who has no trouble seeing the bright side of your problems.
     
Google Groups: rec.org.sca
Let’s calm down…
Vern Hall
12/29/94
(...)
Optimist: One who sees the bright side of your problems
 
24 September 1999, Green Bay (WI) Press-Gazette, Doug Larson column, pg. D-2, col. 5:
An optimist is a person who has no trouble seeing the bright side of your problems.
   
Google Books
I’m the Other Man in My Own Marriage!:
A Frustrating and Funny Look at Family Living
By Howard Noel
San Jose, CA: Writers Club Press
2000
Pg. 95:
Milton Berle used to say that an optimist is a man who always sees the bright side of YOUR problem.
 
12 January 2000, Green Bay (WI) Press-Gazette, Doug Larson column, pg. D-2, col. 4:
An optimist is a person who has no trouble seeing the bright side of your problems.
     
Twitter
Michelle E. Vasquez
@MEVasquezLPC
Great one liners: An optimist is someone who always sees the bright side of your problem. #fb
9:24 AM - 21 Oct 2010
 
Google Books
Happiness Guaranteed or Your Misery Back:
How to Be Happy No Matter What!
By J. Morton Davis and Ruki D. Renov
New York, NY: Page Publishing, Inc.
2018
Pg. ?:
An optimist is someone who always sees the bright side of your problem.
   
Twitter
Gayland Anderson
@GaylandAnderson
An optimist is someone who always sees the bright side of your problem.
9:59 AM - 10 Aug 2018