第 5 季 共 19 集
播出时间：2007年9月25日
第 1 集 Large Birds, Spiders and Mom
播出时间：2007年9月25日
Jake is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.
第 2 集 Media Room Slash Dungeon
播出时间：2007年10月2日
Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.
第 3 集 Dum Diddy Dum Diddy Doo
播出时间：2007年10月9日
Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Alan's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.
第 4 集 City of Great Racks
播出时间：2007年10月16日
Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.
第 5 集 Putting Swim Fins on a Cat
播出时间：2007年10月23日
Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.
第 6 集 Help Daddy Find His Toenail
播出时间：2007年10月30日
Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.
第 7 集 Our Leather Gear Is in the Guest Room
播出时间：2007年11月6日
After Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.
第 8 集 Is There a Mrs. Waffles?
播出时间：2007年11月13日
Charlie writes a children’s song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.
第 9 集 Shoes, Hats, Pickle Jar Lids
播出时间：2007年11月20日
Charlie fights his attraction for Teddy's daughter.
第 10 集 Kinda Like Necrophilia
播出时间：2007年11月27日
Alan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.
第 11 集 Meander to Your Dander
播出时间：2008年3月18日
When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.
第 12 集 A Little Clammy and None Too Fresh
播出时间：2008年3月25日
Rose returns from England, and plays nurse rather oddly for an ill Charlie.
第 13 集 The Soil Is Moist
播出时间：2008年4月1日
Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.
第 14 集 Winky-Dink Time
播出时间：2008年4月15日
Charlie double-dates with Jake and fixes Alan up with a hooker.
第 15 集 Rough Night in Hump Junction
播出时间：2008年4月22日
Alan feels Charlie is unable to control his womanizing ways.
第 16 集 Look At Me, Mommy, I'm Pretty
播出时间：2008年4月29日
Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.
第 17 集 Fish in a Drawer
播出时间：2008年5月6日
CSIs investigate a death at Charlie's house.
第 18 集 If My Hole Could Talk
播出时间：2008年5月13日
Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.
第 19 集 Waiting for the Right Snapper
播出时间：2008年5月20日
When Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.
