| 1 | Kevin | McGregor | Protagonist. |
| | Liz | Hampton | Kevin's wife. Aka: Elizabeth McGregor. |
| | Janie | | Liz's sister. Kevin's sister-in-law. |
| | Tim | | Janie's husband. |
| | Luke | McGregor | Kevin and Liz's son. |
| | Josie | McGregor | Luke's twin sister. |
| | Katie | | Liz's friend. |
| | Ned | | Kevin's step-father. |
| | Caroline | McGregor | Kevin's sister. |
| 2 | Rigby | | Liz and Kevin's dog. |
| | Ryan | | Liz's uncle. |
| | Clay | Bigsby | Kevin's boss. |
| | Chase | Rogers | One of Kevin's co-workers. |
| 3 | Anne | Holloway | The protagonist of the book that Kevin is reading. Aka: Annie. |
| | Tripp | Blakely | The man Annie falls in love with. Aka: George Patrick Blakely III. |
| | Ted | Baskin | Kevin's neighbor. |
| | Trudy | Baskin | Ted's wife. |
| | Jed | | Ted and Trudy's dog. |
| | Jen | Richter | One of Annie's housemates. |
| | Sarah | Danforth | One of Annie's housemates. |
| | Maureen | Lens | One of Annie's housemates. |
| | Joseph | Holloway | Annie's father. A lawyer. Aka: Joe. |
| | Evelyn | Holloway | Annie's mother. |
| | Suzi | | One of Annie's high school best friends. |
| | Ray | Broderson | Annie's first boyfriend. |
| | Steve | Berkshire | One of Tripp's friends. |
| | Pete | O'Leary | One of Tripp's friends. |
| | Paul | Zamenski | One of Tripp's friends. |
| | Ashley | Baron | Tripp's ex-girlfriend. |
| | George | Blakely | Tripp's father. |
| | Katherine | Blakely | Tripp's mother. |
| | Coleen | Blakely | Tripp's sister. |
| | Allison | Blakely | Tripp's sister. |
| 4 | Hallie | Jergens | Kevin's ex-girlfriend. |
| | Julie | | Hallie's friend. |
| | Molly | | Hallie's friend. |
| | Keith | | Kevin's friend. |
| | Jordan | | Hallie's new boyfriend. |
| | Meg | | Maureen's sister. |
| | Knox | Pennington | Ashley's alleged lover. |
| 5 | Reed | Matthews | Kevin's classmate. |
| | Theresa | Hampton | Liz's mother. Kevin's mother-in-law. Aka: Tess. |
| | Jack | Hampton | Liz's father. |
| | Heidi | Radcliff | Annie's enemy. The new sorrority leader. |
| 6 | Eddie | | Kevin's cousin. |
| | Max | | Kevin's friend. |
| | Miles | | Kevin's friend. A musician. |
| | Kit | | Miles's wife. |
| | Laura | | Liz's friend. |
| | Ivy | | Josie's co-gymnast. Laura's daughter. |
| | John | | Laura's husband. |
| | Todd | Fielding | The police officer. |
| 7 | Elsie | | Tim and Janie's daughter. |
| | Davis | Korbin | Liz's ex-boyfriend that both Janie and Tess like. |
| | Jim | Korbin | Davis's father. A former congressman. |
| | Victoria | Korbin | Davis's mother. |
| | Libby | | Liz's roommate. |
| 8 | Courtney | | Annie's friend. |
| | Britanny | | Heidi's friend. |
| | Simone | | Brittany's friend. |
| | June | | The school's registrar. |
| 9 | Quinn | Ford | Luke's assistant coach. Kevin's friend. |
| | Jim | Benson | One of Kevin's larger clients. |
| 10 | William | Faulkner | A famous renowned author. |
| | Pat | Hastings | Ashley's ex-boyfriend. |
| | Tyler | | Pat's friend. |
| 11 | Gabby | | Kevin's office assistant. |
| | Brian | | Kevin's co-worker. |
| | Scott | Hobart | Kevin's neighbor. |
| | Kristi | Hobart | Scott's wife. |
| | Simon | McCallum | Kristi's alleged lover. |
| | Brady | | Simon's son. |
| | Zach | Potter | One of Kevin's neighborhood childhood friends. |
| | Alyssa | Potter | Zach's wife. |
| | Sierra | Potter | Zach and Alyssa's daughter. |
| | Danielle | Potter | Zach and Alyssa's daughter. |
| 12 | Steve | Jensen | Joe's friend. |
| | Charlie | Holloway | Annie's grandfather. |
| | George | Soulick | The author of Jeremy's Wish. |
| | Jeremy | Mallard | The protagonist of Jeremy's Wish. |
| | Benjamin | | Evelyn's dead son. |
| | Simone | Cooperman | An artist. Annie's friend. |
| 14 | Gopher | | Tripp's dog. |
| 15 | Hans | Jorgensen | The Hampton's friends. |
| | Carloe | Jorgensen | Hans's wife. |
| | Bobby | | Tim's brother. |
| 16 | Collette | Brinker | Tripp's ex-girlfriend in Monomoy. |
| | Ernie | Simpson | The CEO of Simpson Hughes. Tripp's boss. |
| | Susan | | Brett's secretary. |
| | Aaron | | Evelyn's new husband |
| 17 | Missy | Hillcrest | Kevin's neighbor. |
| | Baxter | Hillcrest | Missy's son. |
| 18 | Stephanie | Simpson | Ernie's wife. |
| | Gretchen | | Brett's sister. |
| | Jasper | | Brett's groomsmen. |
| | Greta | | One of Evelyn's best friends. |
| | Mila | | A psychic medium and love specialist. |
| 20 | Scarlet | Jennings | Annie's friend in law school. |
| | Neal | Wolcott | Chief Justice of State. |
| | Michael | Eshelman | Tripp's friend who was getting married. |
| | Courtney | Jacobs | Michael's
fiancé. Annie's friend. |
| | Tom | | Michael's best man. |
| | Brad | | Michael's friend. |
| | Philip | | Michael's friend. |
| 21 | Rob | | Kevin's co-worker. |
| | Kyle | | Kevin's co-worker. |
