Tool Academy (season 2)

Original Broadcast - First aired August 30, 2009[6][7]

• Lesson of the Week: Dedication
• Challenge: Testing their dedication from Relationship
• Challenge Reward: A romantic dinner
• Challenge Winner: Justin "J Daddy" and Kathleen
• Bottom 3: John L., Josh, Stew
• Eliminated: Josh (Jamie decided to stay with Josh)
• Episode Notes: After being eliminated, Josh did not go out the main door to meet his girlfriend, Jamie. He said that he would not go out and make himself look like an idiot being the first one to leave. The producer and head of security gave him chances to walk out, saying he was now trespassing, but Josh refused so he was forcibly removed by security, when even there, he hesitated. Jordan ran out, yelling at Josh that he had to leave ("You're a tool, you've been expelled, get the fuck out!"). Security led him out the backway. Josh and Jamie wouldn't leave because Josh wanted the car to be brought to him. Jamie decided to stay with Josh after he said "honest" to her, letting her know he was telling the truth.

Original Broadcast - First aired September 6, 2009[8][9]

• Lesson of the Week: Fidelity
• Challenge: Choreographing a cheer on the good and bad of their relationship
• Challenge Reward: Sexy Photoshoot and Hot Date
• Challenge Winner: Stew and Amanda
• Bottom 3: Dan, Dre P., and Jon S.
• Eliminated: Jon S. (Jon S. decided to leave Tracey)

First aired September 20, 2009

• Lesson of the Week: Modesty
• Challenge: Beet Farmers
• Challenge Reward: Drive-in movie
• Bottom 3: John L., Charm, J Daddy
• Eliminated: J Daddy (Kathleen decided to leave J Daddy)
• Episode Notes: Despite a somewhat strong showing in the previous episodes, J Daddy took neither the mirror exercise, nor the beet picking challenge seriously. Also, Kat and Leah revealed that they work as strippers, which ignited an argument over "ruining happy homes" from Shannon.

First aired September 27, 2009

• Lesson of the Week: Appreciation
• Challenge: The tools must watch their girls go on dates with true gentlemen.
• Bottom 3: John L., Frank, Mike A.

First aired October 4, 2009

• Lesson of the Week: Maturity
• Challenge: Delivering eggs to the "nest".
• Challenge Reward: Romantic Dinner
• Challenge Winner: T Shaw (Terry) and Nicole
• Bottom 3: Stew, T Shaw (Terry), John L.
• Eliminated: John L. (Sarah decided to stay with John L.)
• Episode Notes: The reason for John L.'s elimination was his lack of maturity and his loss of temper, resulting in the damage of school property. He had promised to calm down and not lose his temper as much, but proved he was not able to do so. Terry was almost eliminated because during the therapy session, he blamed his problems on Nicole once again and made excuses. Also, during the challenge, he was more focused on winning than helping Nicole. At the end of the challenge, Shealyn had a sharp pain in her chest. While being checked by the paramedics, Tyler stayed with her the whole time. Therefore, he was first to receive his Maturity badge.

First aired October 11, 2009

• Lesson of the Week: Communication
• Challenge: Build A Living Room
• Challenge Reward: Flat Screen TV, Conjugal Visit Room
• Challenge Winner: Tyler and shealyn
• Eliminated: Dan (Shannon decided to stay with Dan)
  • Bottom 3: Charm, Dre P., Frank
• Eliminated: Dre P. (Leah decided to stay with Dre P.)
• Episode Notes: This episode had a double elimination.
• Reason for Dan's elimination: He couldn't give clear instructions to Shannon, during the challenge, and yelled at her.
• Reason for Dre P.'s elimination: He and Leah were like bombs and they couldn't control their anger.

First aired October 18, 2009

• Lesson of the Week: Trust
• Challenge: Lie Detector Test, Obstacle Course
• Challenge Reward: Romantic Date
• Challenge Winner: Stew
• Bottom 2: Charm, Frank
• Eliminated: Frank (Christina decided to leave Frank)

First aired October 25, 2009

• Lesson of the Week: Romance
• Challenge: Camping Trip
• Challenge Reward: Date (How it was set is determined depending on how they place)
• Challenge Winner: Tyler and Shay (1st), Stew and Amanda (2nd), T-Shaw (Terry) and Nicole(3rd), Charm and Andrea (Last)
• Bottom: Charm, Stew
• Eliminated: Charm (Andrea decided to stay with Charm)

First aired November 1, 2009

• Lesson of the Week: Family Values
• Special Guests: The Tools and Girlfriends Parents
• Challenge: Taking Care of Piglets
• To Do: Catch, Feed, Clean, Change the Piglets
• Challenge Reward: None (Girlfriend, Parent, Tool Baby Shower)
• Challenge Winner: No One
• Bottom 3: Stew, T Shaw, Tyler
• Eliminated: Stew (Amanda decided to stay with Stew)

First aired November 8, 2009

• Final Lesson: Commitment
• Challenge: Clean Mini Van
• Challenge Reward: Romantic Date
• Challenge Winner: Tyler and Shealyn
• Special Guests: Charm, Frank, Stew
• Runner-Up: Tyler (Shealyn decided to stay with Tyler)
• Winner: T Shaw (Nicole and T Shaw got engaged)