As the Heavy, Scout, and Soldier return from a mission to capture a briefcase, Miss Pauling video calls them to ask how the mission went. She is slightly irritated that they left witnesses that she has to take care of for them. After arriving back at the base, Scout tries to ask her out, but he is unable to think of anything to say to her.
At the base, they hear bad news from Engineer and Medic: teleporting bread results in large green tumors inside, leading them to conclude that the mercenaries have the tumors as well, and will all die. The Medic estimates that each team member has about three days left to live. Engineer provides each team member with a wristwatch that will count down to the time of the mercenaries' demises.
In face of this news, Spy decides to collect a bucket list in a literal bucket. Spy delegated the task of collecting wishes to Scout, who has filled it with drawings of the Spy being hit by a car and having a romantic relationship with the Eiffel Tower. Spy remarks that his time has been wasted, and angrily bids the team farewell, after giving the Soldier the bucket. The Soldier then takes his bucket and picks up a loaf of bread dropped by the Medic.
Afterwards, Scout comes to Spy's smoking room to apologize and seek his help. He confides that he did have a real wish for the bucket list: a date with Miss Pauling. Scout admits to Spy that while he himself is good with girls (a scene with the Tramp Girl appears), he is vastly outclassed by Spy when it comes to ladies. Scout then admits Spy is better than him, and Spy demands that broadcast around the base as payment for his services.
Spy agrees to coach Scout in how to behave around a lady. While Scout shows some progress, Spy ultimately declares Scout a failure. When Scout retaliates towards Spy's attitude, Scout decides to do things his own way, which appears to have surprised and impressed the Spy.
With two hours left on his death watch, Scout decides to take things into his own hands. He calls Miss Pauling to the base by pressing the alarm button for the briefcase being stolen. She hurriedly arrives on the scene, but is infuriated upon learning that the briefcase is actually secure. While trying to talk to Pauling, the Soldier, Spy and Demoman spectate from another room. Spy is surprised that Scout is doing surprisingly well.
Meanwhile, through experimentation, Medic and Engineer have come to the conclusion that the growths in the bread are, in fact, not tumors at all, but a self-aware birthmark that can only thrive in pure wheat. This means none of the mercenaries have tumors, and thus are not going to die. They enter the room that Soldier, Spy and Demoman are in and inform them that they are fine as long as no more bread is teleported. To their horror, though, it seems that Soldier's last wish has been to do nothing but teleport bread for the past three days.
Upset at Scout for wasting her "one day off a year", Miss Pauling begins to leave. As Scout attempts to get her to stay, he opens a door, only to be confronted by a giant Bread Monster. A fight breaks out, with the other mercenaries rushing to their aid. One of the Medic's pet doves ends up eaten by the monster.
During the fight, Miss Pauling attempts to blow up the Bread Monster by using a Payload cart, strapping the Scout's death watch to it to serve as a timer. As Scout attempts to help her, she and Scout end up trapped on the wrong side of the blast doors as the bomb is about to blow up. The two notice that the dove that the Bread Monster ate is flying harmlessly out of the mouth of the monster. They wordlessly agree to jump into the mouth of the Bread Monster, which they proceed to do in the nick of time. The Payload cart subsequently blows up, killing the Bread Monster.
Stunned by the blast, Miss Pauling and Scout painfully but quickly recover inside the bread monster. Once she recovers, Miss Pauling admits that the experience was fun. Scout tells her about the death prognosis just as the two are helped out of the remains of the gigantic Bread Monster by the rest of the team. The Medic informs them that only bread mutates, and that they will all be fine (after the Soldier mistakenly states that they will live forever), while the Pyro starts playfully chasing down the remaining small Bread Monster.
The story ends with Scout trying to get another date, but Miss Pauling having to decline due to already having spent her one day of vacation this year. She does, however, offer to have Scout to come along at work, though he declines each task Pauling lists until she comes to the task of killing the one who pulled the briefcase alarm, which she says that Scout will already be at.
