Jim Jennings

Principal Jennings, a character in the My Two First Loves book, is Childhood Crush's father and the principal of Eastridge High. Although he is first mentioned in Chapter 1, he makes his first appearance in Chapter 8.

Appearance
Jim's appearance is determined by which character model is chosen for Childhood Crush.

Personality
Principal Jennings is an ex-military officer who runs the school with an iron fist. He says he is a man of his word. According to his son, Jim is a master manipulator who magnifies everyone else's flaws but can't seem to see his own.

My Two First Loves

 * Chapter 1: The Secret (Mentioned)
 * Chapter 4: The Cheer Squad (Mentioned)
 * Chapter 5: Favors and Fights (Mentioned)
 * Chapter 7: Red-Handed (Mentioned)
 * Chapter 8: The Knives Are Out
 * Chapter 12: The Cover Story (Mentioned)
 * Chapter 13: Polite Company
 * Chapter 22: Trust Fall
 * Chapter 23: Aftermath (Mentioned)
 * Chapter 27: The Meeting (Mentioned; Determinant)
 * Chapter 31: Best Laid Plans (Mentioned)
 * Chapter 36: The Other Boy
 * Chapter 38: Decisions, Decisions
 * Chapter 41: The Half of It
 * Chapter 44: The Whole Truth (Mentioned)
 * Chapter 46: New Tricks (Mentioned)
 * Chapter 47: Overexposed
 * Chapter 49: Up in the Air
 * Chapter 50: What's Not Earned
 * Chapter 53: Miss Movin' On (Mentioned)
 * Chapter 54: Truth, Dare, or Consequences
 * Chapter 55: Friends in Low Places
 * Chapter 56: Inside Man (Mentioned)
 * Chapter 57: Out in the Cold (Offscreen)
 * Chapter 58: Building Bridges
 * Chapter 59: Square One (Mentioned; Determinant)
 * Chapter 60: Slippery Slopes (Mentioned; Determinant)
 * Chapter 62: Cold Blooded
 * Chapter 63: Blank Check
 * Chapter 66: Be My Guest
 * Chapter 67: Crowded Heart
 * Chapter 68: Steamed Up
 * Chapter 70: All Downhill From Here (Mentioned)
 * Chapter 71: What's Done In the Dark...
 * Chapter 72: ...Comes to the Light
 * Chapter 73: Off the Beaten Path (Offscreen)
 * Chapter 74: Staying Alive (Mentioned)
 * Chapter 75: Santa Baby (Mentioned)
 * Chapter 76: Good Tidings We (Mentioned)
 * Chapter 77: Old Acquaintance Be Forgot (Mentioned)
 * Chapter 79: All That Glitters
 * Chapter 80: Enemy of My Enemy (Mentioned)
 * Chapter 82: Nothing but the Truth
 * Chapter 83: Whatever It Takes
 * Chapter 84: Unlikely Allies
 * Chapter 85: Out of the Pan, Into the Fire
 * Chapter 86: Blood, Sweat, and Tears
 * Chapter 87: The A Team (Mentioned)
 * Chapter 89: State's Witness (Mentioned)
 * Chapter 90: Proving the Exception
 * Chapter 91: The Defense Rests
 * Chapter 92: Pleased to Inform You (Mentioned)
 * Chapter 93: Ex Scientia Tridens
 * Chapter 100: Back to the Future (Mentioned)

Childhood Crush
If Main Character asks Childhood Crush about his dad and how he has been over the summer, he'll say that his father is still fuming ever since the Air Force bowl team lost to Berkeley seven months ago. Childhood Crush says that he "collects grudges like badges. And you know how much he loves badges."

In Chapter 23, while Main Character is at the nurse's office, Childhood Crush tells her that he didn't kill Bad Boy but his father came close to killing the both of them for fighting on school grounds. In Chapter 31, Childhood Crush tells Main Character that his dad has been breathing down his neck about his future ever since he started high school. Because Jim went to the Air Force Academy himself, he has always insisted that his son do the same.

In Chapter 63, when Main Character is able to save the arts program with a generous check given by a fan of her photographs, Jim apologizes to her and later to his son. They start to rebuild their relationship but Childhood Crush knows it will take time. In Chapter 66, when Childhood Crush invites Main Character, her family, and Bad Boy to join them on their ski trip during winter break, Jim is angry. He thinks that Bad Boy must be giving his son drugs because there would be no other reason to invite him along. However, he allows the invitations to stand and says he will try to trust his son's judgement.

Main Character
At the end of Chapter 7, Main Character and Bad Boy are summoned to his office. Main Character thinks she's in serious trouble, especially when he is friends with her dad, but he lets her go. Main Character is surprised by it but runs out without questioning it.

In Chapter 13, Main Character, her dad, and her sister meet the Jennings for dinner and Mackenzie wonders how they can afford living in a mansion on a high school principal's salary. If Main Character decided to visit the hot tub earlier with Childhood Crush in Chapter 9, she would share the same question as her sister. During the dinner, he doesn't mention her being sent to his office for breaking school rules and she can choose to tell him that "there are lots of paths to success" or that "sometimes you learn more when you break the rules".

As Main Character begins to assert her own independence and hang out with Bad Boy more, Jim feels she is a bad influence on his son. When Childhood Crush takes her to the beach to try to capture the sunrise on film, Jim refuses to listen to him and angrily throws his son's belongs out of their house. Main Character can do nothing to stop him but leaves as they take their conversation inside their home, away from her.

Best Friend
In Chapter 4, Best Friend suggests they repeat the 'Down and Dirty' routine from sophomore year. Main Character points out that it almost got them expelled as Principal Jennings called it NC-17. At dinner, he appears to agree with Linda's sentiment that Best Friend is a great match for their son.

In Chapter 66, he invites Best Friend to accompany them on their annual ski trip during the winter break.

Bad Boy
At the end of Chapter 7, Main Character and Bad Boy are summoned to his office. While he is talking to Bad Boy in his office, she overhears him mentioning a deal but cannot make out any details.

When Childhood Crush and Bad Boy recall the events that happened during their freshman year to her, Main Character finds out that the two boys had become best friends. Childhood Crush had given Bad Boy the security code to their home as a refuge for whenever Bad Boy needed a break from his family. Bad Boy's older brother, Elijah, had convinced Bad Boy to help him rob the Jennings's home, and on that night, Jim shot Bad Boy, believing the younger boy to be a thief. When his son took Bad Boy to the hospital, Jim identified Bad Boy to the police officers and did not appear remorseful to what had just occurred.

Dave Price
Main Character's dad and Principal Jennings are old friends. Even though their family and the Jennings used to be close when she was younger, they hadn't kept in touch after her mother passed away. They try to maintain a superficial friendship, but in Chapter 72 when the facade cracks, Jim tells them the farce of their friendship should end.

Despite Jim's words, Dave comes to the former's aid when he suffers a heart attack. Dave also monitors him in the hospital after paramedics transport him down from the Jennings' mountain cabin. This appears to be their last interaction before Jim is arrested and incarcerated.

Linda Jennings
In Chapter 100, Childhood Crush mentions that his father reached out to Linda and she has been visiting him in jail for a few months.

Other Looks

 * -|Face 1=

Trivia

 * His character model for face 1 resembles Rodger Crandall from the High School Story: Class Act series; for face 2, he resembles Professor Englund from The Elementalists series; for face 3, he resembles Elliott Taylor from America's Most Eligible.
 * He shares his first name with Jim from the High School Story: Class Act series and Jim Kelly from Endless Summer, Book 3.
 * He shares the same surname as Morgan Jennings from the High School Story series. Jennings is also the default surname of the MC from Save the Date.
 * In Chapter 5, it is mentioned that he was a quarterback when he was in high school.
 * A portrait of him from his Air Force days hangs on the wall of the dining room.
 * In Chapter 54, Childhood Crush will reveal depending on choices that his father likes to sing show tunes while he air dries and gives "You Can't Stop the Beat" from the musical Hairspray as example.
 * In Chapter 72, he falls unconscious due to a heart attack, but survives.
 * in Chapter 82, the group suspects him of accepting bribes from parents to get their children into good universities. This is confirmed in Chapter 89, when Elijah gives the group a ledger with a list of families he accepted bribes from.
 * His crimes include bribery and fraud. In Chapter 92, it is confirmed that he was arrested between the hearing and Spring Break. Following his arrest, he was removed from the position of principal.