Portrayed by: Jean-Luc Bilodeau
- The Bartender
- Bumbling Dad
- The Casanova: Though downplayed due to the love triangle, Ben is nevertheless shown to be a constant womanizer. After all, that's how he got Emma.
- Embarrassing Nickname: Riley called him "Ben-Wetter" in the first episode, but it hasn't shown up again since.
- Green-Eyed Monster: Gets it hard in "There's Something Fitchy Going On", though he also admits that he's still figuring things out and, at the least, he loves Riley enough as a friend to avoid being completely destructive.
- The Hero
- Oblivious to Love: Ben has no clue Riley loves him.
- The Unfavorite: While he was never treated badly, Bonnie tends to dote on pro-athlete Danny and seems more indifferent to former troublemaker Ben (she mentioned in one episode he got really good at making fake IDs.) When moving things out of storage, the majority of the stuff she brought them was boxes of Danny's trophies.
- "Well Done, Son!" Guy: Occurs in "The Wheeler and The Dealer" where everyone thinks he's basically a lazy unmotivated person and he's intent on proving them wrong. It's suggested that this sort of attitude and behavior has been going on for a while. That said, he kind of is Brilliant, but Lazy - his mom points out that he can't just jump in for two days and suddenly become Danny's manager when his actual manager (their mom) has spent years supporting Danny, taking him to practice, going to games, and otherwise being there.
Portrayed by: Tahj Mowry
- Big Guy, Little Guy: The Little Guy to Danny's Big Guy.
- Berserk Button: Don't eat his food.
- Black Best Friend
- Butt Monkey
- Deadpan Snarker: Especially during the moments when he is aware of his status as a Butt Monkey.
- Honourary Uncle: To Emma. He even calls himself her "fruncle".note
- The Lancer
- The Napoleon
- Odd Friendship: With Bonnie.
- Only Sane Man
- Those Two Guys: With Danny. In late season 2 as the Love Triangle between Danny/Riley/Ben takes precedence, he does it with Bonnie.
- Token Minority
Portrayed by: Derek Theler
- Beware the Nice Ones: He's mostly a sweet-hearted lug who a little bit of a Momma's Boy, but if you hurt someone he cares about (especially Riley,) you will regret it.
- The Big Guy
- Big Guy, Little Guy: The Big Guy to Tucker's Little Guy.
- Big Brother Instinct: When one of Riley's boyfriends punched Ben, Danny immediately stepped in:Danny: Big mistake. [punches him in the face]
- Cool Big Bro: To Ben.
- Cool Uncle: To Emma.
- Dogged Nice Guy: When it comes to Riley, he's the complete polar opposite to everything he normally is.
- Dumb Muscle: At times, Danny doesn't come across as too bright.Bonnie: It takes him a while, but he gets there eventually.
- Embarrassing Tattoo: He plans to get his girlfriend Amy's name tattooed on his wrist to show his devotion to her, but because he's so heavily drunk, he ends up with Riley's name. He eventually does get the "Amy" tattoo on his other wrist... only hours before Amy dumps him.
- Gentle Giant: Especially whenever he's with Emma.
- Ladykiller in Love: Towards Riley.
- Lovable Jock: He's a pro-hockey player who clearly loves and prioritizes his friends and family over the visages of wealth.
- Momma's Boy: He's still very close to Bonnie and is actually a pretty positive example, however, in "Go Brit or Go Home," once he realizes that Bonnie's been running interference to help his hockey career, he does tell her she needs to back off and let him fight his own battles.
- Mr. Fanservice: It's apparently in Derek Theler's contract that he appears shirtless at least once every second or third episode.
- One Head Taller: Derek Theler is 6'5 so he ends up being comically taller the rest of the cast.
- Security Blanket: His lucky jersey from high school, which he wore under his uniform at every game (and never washed). Until Tucker shredded it in the washing machine, then he realized he could move a lot better without the undersized garment restricting his movement.
- Those Two Guys: With Tucker.
- Violently Protective Boyfriend: Interestingly enough, despite never actually having been Riley's boyfriend, Danny still fits in this role. Hurt her in any way, and you will have six-and-a-half feet of pissed-off pro-athlete raining down on you. His own brother Ben has found this out repeatedly.
Portrayed by: Melissa Peterman
- Action Mom
- Christmas Cake
- Deadpan Snarker
- Doting Parent: To Danny, but not so much with Ben. She's also become a doting grandmother to Emma.
- Former Teen Rebel: She was a bit of a wild child when she was young as seen when Riley finds out about Bonnie's first wedding in Vegas when she was eighteen.
- Genki Girl
- Girly Bruiser
- Jerk with a Heart of Gold: She's pushy and thoughtless at times, but she wants the best for her sons and granddaughter.
- Mama Bear
- My Beloved Smother: She has no boundaries when it comes to her sons.
- Odd Friendship: With Tucker.
- Playing Gertrude: Although Bonnie's Vegas wedding at eighteen implied she was fairly wild as a child, Melissa Peterman was still only fifteen when Derek Theler (Danny) was born.
- Statuesque Stunner
- Team Mom
- Obliquely Obfuscated Occupation: Averted in the sense that she said in a video dating profile she was unemployed, but it still leave the question: How the hell does she have the money to live in New York City [while it isn't the most expensive city in the world anymore (that's Tokyo,) it's still up there,] and spoil Emma at every opportunity? The closest thing we've had to an explanation is revealing her ex-husband was a successful realtor, so she might just be leeching off alimony. She's also revealed to be Danny's manager so while she may not consider that her 'job' (in that she does it as much to protect Danny as anything else), he or the team may still pay her or otherwise cut her into his salary. Later on, she's seen wandering from job to job, such as selling real estate and giving makeovers.
- She is now married to ANOTHER successful realtor.
Portrayed by: Chelsea Staub
- Berserk Button: Do not call Riley "Fat Pants" or she will put you in a headlock and slam your head into hockey glass.
- Beware the Nice Ones: When she got fired from her job at a law firm for being "too nice" and not having the killer instinct a lawyer needs, she (thanks to a Wounded Gazelle Gambit from Bonnie) threatened to sue the firm for Bonnie's (pretend) injuries, and threatened to make every single dirty trick the firm ever did a matter of public record. She ended the whole thing with a big smile and saying "Who's too nice now?" She got her job back.
- Butt Monkey: On more than one occasion, the insanity of Ben and Co. has spilled over to cause mayhem in her life.
- Childhood Friends: With the Wheeler brothers.
- Competition Freak: As seen in "Take Her Out of the Ball Game".
- Cute Bruiser: Riley was known for playing field hockey and beating up Ben when they were kids and she's still very much capable of taking down a huge hockey player like Danny.
- Deadpan Snarker
- Embarrassing Nickname: "Fat Pants" and "Rigantor".
- First Love: Riley is suggested to be this to Danny since he's had a crush on her since they were little. Considering how completely devoted he is to her, there's the implication that every other relationship he's had ultimately fails because they never compare and because ultimately, he's emotionally committed to Riley. See "I'm Not That Guy" where the moment Riley is in trouble he rushes to the rescue - despite that he's suppose to be going on a date with the girl he's seeing.
- Formerly Fat
- Go-Getter Girl: Riley has devoted herself to graduating from college, getting into law school, and successfully transforming herself from Fat Pants Perrin to Hello, Attorney!. Though living up to the image she's created can sometimes get to her.
- Honourary Aunt: To Emma.
- Oblivious to Love: Riley is really clueless about Danny. In "There's Something Fitchy Going On", she finds out and it's implied she was ready to return the sentiment... until Danny's current girlfriend turns into a Moment Killer.
- Passionate Sports Girl: She was really into sports as a teenager and "Take Her Out of the Ball Game" shows that she's still got it.
- The Smart Girl
Portrayed by: Ali and Susanne Hartman in Season 1, Zoey and Mila Beske is Season 2, Ember and Harper Husak in Season 3.
- The Cutie
- The Other Darrin: They rotate in a new set of twins to play her every season.
- Has Three Daddies
- Missing Mom
- Tagalong Kid