The series begins in April, but the year is unknown. There are several possible years which the series could be in.
The series can be considered to start in the year it was released, 2011-2012. The technology mentioned in the series appears to match that time as well (PSP's, iPhone 4s, etc.).
A second possibility is revealed in light novel Volume 4. In chapter 1, there is mention of Saburo Omura returning to play for the Chiba Lotte Marines baseball team. He was traded midway through the 2011 baseball season (April - October). After the season he re-signed with the Marines for the 2012 season. This sets an exact date of August 2012, and dates the series as 2012. It might just be an author oversight as this novel released in 2012.
A third possibility is when the anime was released in 2013. Many posters in the show are labelled to say 2013.
A fourth possibility is revealed in Season 2 Episode 3. At one point in Season 2 Episode 3 a calendar showing "Monday the 1st" with only 30 days in the month. There are only 3 months from 2010-2015 that this could be. The episode happens in November and the only date this matches is November 2010, setting a possible timeline for 2010-2011. However the 8th is a holiday that does not match that particular date.Anachronism: In Volume 14, Hachiman makes reference to the Reiwa era of the Japanese calendar, which did not begin until 2019.
Second Year Middle School
Hachiman accidentally talks to a girl. It was the last time he talked to a girl until he met Yukino.
Third Year Middle School
First Year High School
- Hachiman's accident. Hachiman was riding his bike to school an hour early. He happened to see a dog run into the street which he rode into the street to retrieve. He was hit by a limousine/private car fracturing his left foot, making him miss the first two weeks of school.
- Yui visits Hachiman at his home, he hides from her. Yui meets Komachi.
Second Year High School
- Iroha Isshiki's birthday is April 16.
- The Service Club is formed
- Komachi meets Taishi at cram school.
- Volume 3
- Yui's birthday is June 18.
- Minami's birthday is June 26.
- It is the start of Summer Break
- Volume 4
- Hachiman's birthday is August 8.
- Volume 5
- Kakeru's birthday is August 29.
- Volume 5, Chapter 7 is August 31
- Volume 5, Chapter 8 is September 1, and the first day at school after summer break.
- Hayato's birthday is September 28.
- Volume 7.5 Side A - OVA
- Volume 7.5 Short Story 2
- Volume 7.5 Short Story 3
- Volume 7.5 Short Story 4
- Saki's birthday is October 26.
- Roughly the time of the Kyoto trip.
- Yoshiteru's birthday is November 23.
- Volume 8 Chapter 7
- Volume 8 Chapter 9
- Yumiko's birthday is December 12.
- Volume 9 Chapter 0
- Mid December is the start of Winter Break.
- Christmas Eve December 24 is the Christmas Collaboration event.
- Volume 6.5 Drama CD Christmas Day, December 25.
- Volume 10
- January 2 Yui and Hachiman shop for Yukino's birthday present. They meet Yukino and her mother at the mall.
- Yukino's birthday is January 3.
- January 4, first day back from Winter Break.
- Meguri's birthday is January 21.
- The School Marathon is held at the end of January (It's normally early February).
- Volume 10.5
- Volume 10.5 Chapter 3
- Volume 11
- February 13 is the Pre-Valentine's Day event.
- February 14 is Valentine's Day, the Aquarium date, and the first day of Komachi's Sobu exam.
- February 15 is the second day of Komachi's Sobu exam.
- Volume 12
Third Year High School
- ↑ Volume 1: Chapter 1 indicates April or May.
- ↑ Volume 2, Chapter 4 indicates its after April.
- ↑ The judo tournament takes place before Summer break.
- ↑ Volume 4: Chapter 1 Mentions July has ended. Volume 5 Chapter 1 mentions Volume 4 happened in early august.
- ↑ Volume 5: Chapter 5 mentions they are in the second half of August.
- ↑ Volume 6 Chapter 1 Mentions they are a few days into September and nearing the Second semester.
- ↑ Fall/Autumn after the culture festival. Questionable. It mentions its after the Culture Festival. However the first mention of of the email consultations is technically in Volume 6.5, so this goes after both Festivals.
- ↑ It is mid autumn. Short Story 1 is the prelude.
- ↑ Fall/Autumn is intensifying.
- ↑ The height of autumn.
- ↑ Volume 7 Chapter 1 says the year is over in less than 2 months, November. Chapter 5 says late autumn.
- ↑ Its halfway through December.
- ↑ Chapter 1 mentions Its almost New Years.
- ↑ Its the end of January, to early February.
- ↑ Starts 2nd week of February