In Nowhere to Run, now that Jake and Clare broke up Jake was sad so he invited some friends to his cabin. Alli was sad about her recent break up with Dave so she went with them too. They both needed a rebound and were sitting close by the fire they made roasting marshmallows. It was the perfect moment, so Alli looked up at him and they kissed. Clare and Bianca arrived just in time to watch, ruining Alli's friendship with Clare. Ever since, Alli and Jake have been strictly friends.
In LoveGame, Alli and Jake walk past each other when he walks into Clare's house. They stop, smile, and look at each other. Alli tells Clare he is cute and she tells her he was a jerk when they were kids. Alli leaves but is sure to tell Jake goodbye and blush while doing so. Later Alli is at Above The Dot after school with Dave, K.C., and Sadie. Clare and Jake arrive and Clare formally introduces her, Sadie, Dave and K.C. to Jake. Alli then asks Clare if he has met Eli and Clare gets annoyed. The next day, Clare tells her she and Jake kissed and Alli looks shocked.
In Cry Me A River (1), Jake is seen setting up an Orienteering booth at the Clubs Fair when Alli says that Clare should join (referring to the Jake and Clare kiss in LoveGame). Clare then exclaims that she is not interested and that she and Jake were a one time thing. Alli smiles.In Nowhere to Run, Dave confesses to Alli that he cheated on her with Jacinta. They break up and Alli is very upset. Jake sees her downtown while he is upset and his friends are trying to cheer him up from Clare's break up, and he invites Alli and the rest to his cabin to get away from everything and have fun. So they go to the cabin, and when they want a campfire, Jake picks Alli to come help him get firewood. They make the fire together, and after talking about their sad lovelives, end up sharing a kiss. Clare comes just in time to find them and this ruins Alli and Clare's friendship. Jake apologizes but Alli ignores him and runs to try to fix things with Clare, until she runs alone into the woods. Alli goes back inside and pouts about Clare being alone and it being her fault.
In Not Ready To Make Nice (1), Clare is mad that Jake is supposedly dating a new girl and assumes its Alli since the two kissed. The girls yell at each other in the classroom and it turns out that Jenna has been hanging out with Jake. Clare then brings up K.C. and calls her the boyfriend stealer. Later in the season Jenna finally confirms her and Jake are only friends, and Clare claims to be over him anyways.
From here on out, Jake and Alli remained strictly friends to avoid drama.
In Come As You Are (2), she ask Jake to help Clare with her Eli problems, and he jokingly walks away but Alli calls his name in a serious voice and he comes back. They talk and seem to be normal after everything that happened a couple months ago.
- Jake is the second boy that Clare liked that Alli kissed. The first is K.C. but Clare did not know about that.
- Jake dated Alli's best friend Clare.
- Jake's first line was about Alli.
- Both Jake and Alli are friends with Eli.
- Alli is dating Jake's rival, Dallas.