Released May 29, 2014. Rodrick gets HOLLY to date GREG when a love plan for Heather Hills backfires, and Rodrick is grounded for three and a half months.
This book covers the months of May, June and July. On May 1, Greg is preparing for the skateboarding competiton.
On May 7, Rodrick tries to steal his skateboard, but he is bagged by Mom and Dad and is grounded until the start of the competition. Greg wins the auditions by doing a 900, indy, impossible and 996 others.
512 students enter the compeition, and, Patty Farell and the We Want Greg To Suffer And Die In Pain kids enter to hurt Greg, but Rowley makes it backfire by jetpacking into Patty, Bryce and Shelly. Then, after the first round, Rodrick tosses Greg's third diary (The Last Straw) to Heather Hills, but THAT plan for love backfires when she throws it to Holly Hills, which led to her learning Greg's feelings and going after him (secretly for now)
In the second round, Rodrick, one of the 256 remaining students, tries to outpeform Greg, which fails as he is distracted by Emma Ontario, the most popular girl in her class. He falls, making Greg laugh at him.
In the Round 2-3 intermission, Holly tosses Greg's third journal to him, which leads to him practially fainting when she notes in HIS diary "You are the most adorable person I've ever met. Can I ask you out?" Rodrick sees the note and gets even more mad, but Heather Hills notes to RODRICK "You are probably jealous of your own younger brother." which he is, but before he can note back to Heather, he is knocked out of round 2, and they move on to the last 128 students, including Greg and MANNY (a ten year old sixth grader in BlazeRush7's Fandom.) Susan sees Holly Hills' note to Greg when he throws the journal to her, and wildly approves of it. Greg knows that his biggest compeitior in round three is James Stewart, and he has to pull off a 900 if he wants to succeed, because James can pull off a 720 indy. He sucessfully pulls off the 900 Indy, and knocks James out. Manny is still going in the last 64 students, and the round 3-4 intermission starts. Rodrick notes back "Can we go out after this?" Heather replies "Yes, but not today." Rodrick is overjoyed by that statement, because she usually screamed "NOOO" He replies "Why?." "Because now I have to cope with Greg for the next day. Make it two days." "Oh. Maybe we should use email." "Yeah. I was thinking that as well."
Greg finally gets chance to respond to Holly's note with "YES YES YES YES YES!!!", to which they agree to go out after the skateboarding compeition, and stay over. After, he asks Mom, which was stupid, as she said YES YES YES YES YES!!!. He then shows every kid in his grade that Holly asked him out, with Frank (Not Greg's dad) moaning "Looks like we have to compete for the FIFTH-prettiest girl now." Shelly, the fifth-prettiest girl, is OVERJOYED because now she has 30 roping for love. Then Round 4 starts. Greg feels that everything's turning his way. No military school, Holly (yay), and better Phys Ed grades (C instead of a D-) He rocks the last 64, with Manny, Elina and Heather Hills not far behind him. Rowley gets knocked out of round 5. It was starting to get intense at the round 4-5 intermission, as there are only 32 of the 512 students still in the compeition, after only 35 minutes. Holly Hills notes to Greg "Do you think Abigali will keep Rowley?" to which he replies "No. He's already made 16 bad impressions on her. I counted." Greg is passed to round 6 AND round 7/quarter finals because he had most points in rounds 1-5 overall. Rodrick, watching Greg and Manny flippin' it out together, decides to train up for next year. Meanwhile, Shelby is already being laughed at by Holly Hills because she fell from fourth to fifth prettiest because she had plastic surgery. And is now having 17 boys trying to win her love. Manny hits the fifth round to another pass. Rodrick wonders why Greg and Manny are so good at skateboarding. He suddenly rerembered that Greg was learning for eight years then when Manny was six he taught him how to skateboard, and he taught Lily to skateboard when she was five and a half. Only 16 students left. 496 students knocked out.
Greg thought "God. Gettin' intense." he flips over and does a 1460, which got him 600,000 points.and a world record. Holly Hills nearly breaks her leg. However, Holly notes to him "Abigali's dumping Rowley."
He eventually, on the finals, is put up against Manny. He wins by 60 points. Then there is a small blizzard, but it didn't stop Greg and Holly's date. At their date (two days), Heather Hills texts Rodrick that he can come round as soon as Greg leaves. But, the snow melts, and floods every single house with an inch of water. Somehow, it doesn't affect their electricity, water and food supplies. Greg did need a cushion to play video games for two weeks, because the floor was soaked. Same for him and Holly's second date.
School starts up from summer again, and Greg has to introduce Manny to middle school, before he gets shocked to realise that he wants to start a band. But, this time, good music. He starts a band, and he rises to #1 most popular.
"Rodrick tried to STEAL my SKATEBOARD. Grounded for a long time."
"RODRICK BACKFIRED AGAIN!" (every time something went wrong with Heather Hills)
"Boom. 600 points is so damn easy." (3 times, Round 1)
"WHO LET HEATHER HILLS READ MY DIARY!!! ESPECIALLY THAT ONE!!!"
"Yes! Round 2's 1600 points!"
(after Heather Hills tossed Greg's third diary to Holly) "Best move she's ever done. This might help her understand my feelings."
"(speechless, after Holly asked him out) "YES!! *runs off to show Rowley*"
"*after* Yay, Holly likes me."
"Right. Let's get serious. Guys, I really do have Holly Hills. Look at this note."
"Who the heck is Emma Ontario?!"
"Round 5. Here we go. 32 left."
"THERE GOES HEATHER HILLS!!!" (Round 7)
"Aww. Holly's out." (Round 8)
"YES! I WON!"
"Small blizzards don't matter."
"I kissed Holly. Really, I swear."
"Well an inch isn't Hurricane Katrina. "
"Hey, that was fun splashing around in your own house." (Holly Hills' reply: Yes. It was so epically awesome."
"Ahh. A cushion.
"Second date may be a bit wet."
"Kissed Holly about five times and talked to her about 600.
"Next time, Rodrick, you will get your dream love. in fact, you went out with her."