Notable love interests
Joanie is the daughter of Frankie, a single mother on the run from her In-Laws after her husband’s death during season 1. While Frankie was aided by Alan and Charlie at their house, Joanie developed an instant crush on Jake. She tried to pursue her crush by playing games with Jake, and having the same choice of lunch as his. Jake, however, did not return her feelings, when Joanie kissed him bye, he responded by “Oh Man!” and cleaning her kissed spot from his hand.
Unseen in the series, Robin Newberry was a classmate of Jake in season 3. She had a crush on Jake, showing her feelings by giving him cupcakes. Jake turned to Charlie for advice regarding an appropriate response, to which Charlie told him to enjoy the cupcakes without any obligation to like her back. Alan considered it as a wrong advice, and asked Jake not to do so. Jake went on to become exclusive with Robin in order to get daily cupcakes. When Robin dumped him, he learned to bake cupcakes himself.
Another unseen character, Wendy was Jake's first real girlfriend. First mentioned by Jake as the smartest girl in his class, their relationship began at Wendy's party in season 3's ‘Just Once With Aunt Sophie' after Charlie gave Jake advice on how to approach her. She broke up with him in season 4's ‘A Pot Smoking Monkey’; due to the differences in their academic abilities.
Seen in season 4's ‘Release the Dogs’, Taylor was a friend of Jake’s on whom he had a crush on. He invited her over for a play date. However, their relationship was made awkward when Charlie meet and went out with Taylor's mom Kelly, even though he had promised Jake otherwise.
Featured in season 4's ‘Tucked, Taped and Gorgeous’, Sophie is the daughter of Greg, Alan’s gay friend. The pair is taken by their parents on movies and boating. Sophie is shown to be attracted to Jake too, as she openly wants to kiss him, but Jake’s lack of intelligence prevents it. They presumably stopped seeing each other because Jake accused Alan of "breaking up with" Greg after the latter found Charlie "attractive."
Dubbed the ‘hottest girl in Jake's class’, Nicole is mentioned in season 5's ‘Kinda Like Necrophilia’. Jake asks her out when Charlie advises so, and though initially confused as to who he was, Nicole accepts to go out with Jake. In season 7's ‘Fart Jokes, Pie And Celeste’, a girl referred to only as Nicole calls Jake and invites him down to the pier after she hears he broke up with Celeste. It is unknown if this is Nicole O'Malley; Jake tells Alan he doesn't know who she is, but it's possible he simply doesn't remember her. In season 7’s ‘Tinkle like a Princess’, Jake is seen on Charlie's deck with a girl named Nicole, who claimed they were dating but its unknown if she was the same Nicole.
Celeste was Jake’s first girlfriend who lasted a little longer than others. She was first featured in season 6, when she moved in with her father in Charlie’s neighborhood. Later, Jake goes out on a date with her. She later appears in season 7, once seen controlling Jake, and later breaking-off with him when Jake cheats with her during Christmas, though that was due to Charlie’s ill advice.
Tiffany & Joanne
Two different girls shown during season 8, it is highly possible that Jake had his first adult relation with them. Caught sneaking out from Charlie’s home first, they are later seen by Charlie sneaking out from Judith’s home too, implying that Jake was with them both.Megan is introduced in Season 8, who is with Jake, but leaves presumably due to Charlie’s drunken behavior. She later appears in Season 9 after Charlie's death as Jake’s chemistry tutor in Thank You For The Intercourse, and seemingly gets attracted to Walden, but when she couldn’t get him, she shows the same feelings to Jake. They seemingly start a relationship. It is assumed that she and Jake are no longer together, as he had sex with a older woman named Jennifer in "Not In My Mouth!".
A bubbly woman who lives in Zoey's building, who appears in "Not In My Mouth!". Walden attempts to begin a new relationship with her after Zoey refused to him he loved her. He brought her to the beach house to get better acquainted with ber but she unintentionally walked in on a conversation he was having with Zoey via FaceTime. Jake is instantly smitten with her and lies about his age in an attempt to get close to her. In an unexplained move, he eventually sleeps with her (offscreen) while the adults are gone and tells a friend (possibly Eldridge) over the phone that they had sex 5 times in a 30 minute period, claiming it to be the best half hour of his life. This could only imply that he pre-ejaculated several times.
Dated Jake. They broke up because Jake said to her that she is old.
In You Know What The Lollipop Is For when Missi visits Walden's beach house, Jake returns for one weekend to the beach house and he immediately become interested in Missi. They walk around in the beach and they kissed. They have sex and Jake thinks he and she began a relationship, until Missi reveals that she has a boyfriend so they broke up. Missi re-appears in Avoid The Chinese Mustard when they comeback together, but Jake is forced to go back to the army, so Jake planned to escape with her because he thinks they love each other, but they broke up again because Missi couldn't say that she loved him.
A 36 year old woman that Jake met when he walked into a tattoo store, called Tammy's Tatties, owned by Tammy
Ashley is Tammy's 18 year old daughter, who Jake cheated on Tammy with. Tammy gets angry and confronts Jake, but Ashley later shows up and reunites with him. She leaves at the end of the episode when she agrees to marry her older ex-boyfriend with the promise of a new car. She is portrayed by Emily Osment.
Note: During the episode, Walden refers to Ashley as "Hannah Montana." Emily Osment had a main role on Hannah Montana playing Lily Truscott. She co-starred along with Miley Cyrus, who played Missi in "You Do Know What The Lollipop's For" and "Avoid The Chinese Mustard."