Two and a Half Men — Season 5 CBS Ended Comedy 19 Episodes · Premiered September 24, 2007 · Ended May 19, 2008 ← Season 4 All Seasons Season 6 → Episodes E01 Large Birds, Spiders and Mom Tue, Sep 25 2007 1:00 AM GMT+0000 30 min ★ 6.8 ▶ Charlie and Alan try to prepare Jake for his first day of Junior High, but may wind up traumatizing him instead. E02 Media Room Slash Dungeon Tue, Oct 2 2007 1:00 AM GMT+0000 30 min ★ 8 ▶ Charlie reacts oddly after an evening with his mother, and Alan's date reacts oddly after having sex with him. E03 Dum Diddy Dum Diddy Doo Tue, Oct 9 2007 1:00 AM GMT+0000 30 min ★ 7.1 ▶ Suffering from bimbo fatigue, Charlie lets Alan set him up with a woman his own age. E04 City of Great Racks Tue, Oct 16 2007 1:00 AM GMT+0000 30 min ★ 7.1 ▶ Charlie gets closer to consummating his relationship with Linda, but begins to see Rose's face everywhere he turns. E05 Putting Swim Fins on a Cat Tue, Oct 23 2007 1:00 AM GMT+0000 30 min ★ 7.5 ▶ Charlie has to find creative ways to entertain his girlfriend's 4-year-old son, while Alan becomes a human guinea pig. E06 Help Daddy Find His Toenail Tue, Oct 30 2007 1:00 AM GMT+0000 30 min ★ 6.9 ▶ Charlie's girlfriend is embarrassed to be seen with him in public. Meanwhile, Jake sneaks out to a concert despite Alan's forbiddance. E07 Our Leather Gear Is in the Guest Room Tue, Nov 6 2007 2:00 AM GMT+0000 30 min ★ 6.5 ▶ Charlie and Alan butt heads over Alan's place in the house, prompting Alan and Jake to move in with Evelyn. E08 Is There a Mrs. Waffles? Tue, Nov 13 2007 2:00 AM GMT+0000 30 min ★ 8.4 ▶ Charlie finds success as a children's singing star, which makes Alan miserable. E09 Tight's Good Tue, Nov 20 2007 2:00 AM GMT+0000 30 min ★ 6.8 ▶ Charlie tries to resist his attraction to his soon-to-be step sister. E10 Kinda Like Necrophilia Tue, Nov 27 2007 2:00 AM GMT+0000 30 min ★ 7.6 ▶ Alan seeks revenge when he discovers that Charlie stole his high school girlfriend. E11 Meander to Your Dander Tue, Mar 18 2008 1:00 AM GMT+0000 30 min ★ 7.5 ▶ Charlie coaches Alan in the fine art of breaking up with a woman. E12 A Little Clammy and None Too Fresh Tue, Mar 25 2008 1:00 AM GMT+0000 30 min ★ 6.8 ▶ Rose is back from England and takes very strange care of a very sick Charlie. E13 The Soil Is Moist Tue, Apr 1 2008 1:00 AM GMT+0000 30 min ★ 7.6 ▶ Alan dates one of his ex-wife's friends who reveals a secret about Judith's sex life. E14 Winky-Dink Time Tue, Apr 15 2008 1:00 AM GMT+0000 30 min ★ 7.5 ▶ Charlie goes with Jake on a double date and sets Alan up with a prostitute. E15 Rough Night in Hump Junction Tue, Apr 22 2008 1:00 AM GMT+0000 30 min ★ 7.7 ▶ Alan worries that Charlie's womanizing is out of control. E16 Look at Me, Mommy, I'm Pretty Tue, Apr 29 2008 1:00 AM GMT+0000 30 min ★ 7.1 ▶ Alan plans Evelyn's wedding while Charlie pursues his future step-sister. E17 Fish in a Drawer Tue, May 6 2008 1:00 AM GMT+0000 30 min ★ 8.2 ▶ The team from CSI investigates a mysterious death at Charlie's house. E18 If My Hole Could Talk Tue, May 13 2008 1:00 AM GMT+0000 30 min ★ 7.1 ▶ Charlie finds himself attracted to an older woman who writes self-help books, while Alan and Jake battle over a school assignment. E19 Waiting for the Right Snapper Tue, May 20 2008 1:00 AM GMT+0000 30 min ★ 7.5 ▶ Charlie tries to resist temptation when he meets the grown daughter of the woman he's dating and realizes they've met before. ← Season 4 All Seasons Season 6 → Similar Shows Cristela ABC New Girl FOX The Mysteries of Laura NBC Bob's Burgers FOX Parenthood NBC The Carrie Diaries The CW Top Rated Shows Breaking Bad AMC ★ 9.2 Band of Brothers HBO ★ 9 Game of Thrones HBO ★ 8.9 The Wire HBO ★ 8.9 Firefly FOX ★ 8.9 Sherlock BBC One ★ 8.9 More on CBS The Twilight Zone ★ 8.9 Person of Interest ★ 8.8 M*A*S*H ★ 8.5 Elementary ★ 8.3 The Unit ★ 8.3 The Mentalist ★ 8.2