Timeline List of "May I Help You" (Spoilers)

Since so many people seem confused as to what the timeframe of the drama is, let me help you out with a coherent timeline table. All dates I am using are either taken from the first episode or the visual clues about dates documents/dates of admission of the deceased/people at the obiturary room's sign gives us. Plus a little bit of deduction through what the characters tell in their dialogue is used here too. Spoilers, obviously, so go watch the drama first and come back if you need clarification regarding its timeline.

• End of 2019/Begin/Mid 2020 - FL Baek Dongjoo injures her foot at a ping pong tournament and has to give up her professional career. Starts studying for civil exam for a couple of months, but fails to pass. Takes up a job interview as a funeral director to earn money instead.
• First Half Of 2020 ML Kim Tahee graduates from medical school and starts working as a doctor at the local hospital.
• October, 9th 2020 - Ten year old Kim Jeon Ho who is Taehee's kid brother dies in car accident. Dongjoo starts working at the funeral hall at the same time and has her supernatural encounter with the same boy who died in the accident. She flees from the job at day one, scared out of her wits.  About at the same time ML Kim Taehee breaks up with his first love and fellow medical alumni Chungha, too burden with guilt about the accident to continue their relationship.
  October/November 2020- Blaming himself for the incident, Taehee hands in his resignation as a doctor and leaves Seoul to do his 18 months of mandatory military service, cutting ties with everyone. 
• November 2020- January/February 2022 Dongjoo goes back to studying for the civil exam, while completely ignoring the supernatural event that took place. She suffers a streak of bad luck/injuries as consequence for not helping to fulfill the last wishes of the dead people, as she is supposed to.
• February/March 2022 After an extensive talk with a priest named Michael at church, (who knows of her abilities and is her uncle) and another injury suffered that has her temporarily wheelchair-bound, Dongjoo decides to go back working at the same Funeral Hall to fulfill her duty toward the dead people and their wishes. So that she can end her streak of bad luck and be freed of this involuntary task and job in six months. She has to fulfill 21 wishes in total. Since the occupation is looked down upon and due to her father's strong objections toward it the last time, she doesn't tell him she is working again as Funeral Director and pretends to continue studying instead.
• April/May 2022 Taehee returns from military service to Seoul and starts living with his uncle Vincent, who is about to open up his own business; a helper service named "A Dime A Job." Taehee remains distant to his parents/family outside of Vincent.
• May/End of May 2022 ( : Starting events of the drama take place (episode 1-3, since DJ's birthday is in eps 2 and shown to be on 5/24/98 on the birth certificate) Taehee begins working at his uncle's helper service company. With the case of the cheaters solved in episode 1, Dongjoo has  now only 12 dead people left to help. Dongjoo and Taehee meet when DJ's boyfriend hires TH's services to deliver his breakup message to her, which goes as well as you think it would. Their paths keeps crossing after that, again and again, turning bickering strangers into sort of-friends. Dongjoo moves out from her father's home into the vacant first floor apartment of the house Taehee's uncle Vincent owns/lives in with Taehee. Taehee starts to become romantically interested into Dongjoo (the shift of his tone toward and amount of flirting with her in episode 3 is very telling, lol)
• June-Juli 2022: Time of events in the drama of eps 4-8, which takes place over a few weeks. (Apple Mom's death is shown to be around 6/9/22.) DJ moves back into Vincent's house after her misunderstanding with Taehee is cleared. TH and DJ help a ghostly client together in the countryside. Now there are 9 dead people's wishes left. Finding comfort/a kindred spirit in each other, TH and DJ are growing closer and closer together. To the point where TH opens up about his past trauma/feeling of guilt to her. Chungha learns of Taehee's return to Seoul and reappears in his life, uninvited.  
• August - September 2022 There are more timejumps/blanks in the drama timeline of the eps 9-10 going forward. Dates from the obituary room and mobile phone show that it skips a few weeks ahead here and there. It becomes more inconsistent with what is shown, since the plot/events feel like happening in a matter of days. Oh well, lol. The whole confrontation with Chungha in episode 9 for example happened around 8/23/2022, so she stays at his house for 2-3 days, since the reservation for the dinner for two one she made is on 8/26/2022. Dongjoo confesses to Taehee on the same evening. Which means we have around a week blanks/awkward denial/rejection limbo between the leads (?), because the wedding they are invited to is on 09/04/2022. On the same evening TH apologizes and confesses to DJ. They share their first kiss and start dating. 
• September - October 2022 Timeline of the episodes 11-12. Timeskippy ahoi., it gets wild date-wise. Because while the first bit is set right after their kiss, DJ/TH's dating era starts with a montage that suggests a timespan of a month, because as soon we see another date it is October. So what looked like two days of dating at best was moments of a month of dating. Cool. Chungha's mother's date of admission is the 10/03/2022 in the funeral hall and Kim Joon-ho's second death anniversary is on the 9th of October 2022. Dongjoo and Taehee know each other for almost five months now. So when exactly is their wedding?

Glad it helps :) As for when she searches for the ring and her seeking out the home of the family, it is not explicitly stated. Seeing how the boy haunted her mind to the point she did hide under her blanket, i think it is around a couple of days up to a week after she ran away from her job in fear (and avoidance became too hard)

At least enough time must have passed after the boy's funeral for Taehee's family to be able to pack up things and leave the city. So a week sounds about right.

Also in a talk with the priest Michael later on where DJ voices her regrets of failing to fulfill the boy's wish, he mentioned that Dongjoo tried a lot to find them, contacting institutions etc for their whereabouts, but to no avail. This fact will also help to soothe Taehee's likely anger that finding the ring at DJ's place (which is bound to happen soon, lol) will cause, i am sure.  

 Ivy:

What gets me is that she lasted 2 years being haunted by the kid?! 

Right? Never underestimate the power of ignorance is bliss I guess hahaha. But I feel it is the normal reaction to compartmentalize it this way at first before believing you can wake up dead people with your touch and talk to them about their last wish xD (And technically it was just a bit more than a year before she started working as funeral director again.) 

So it is no surprise that Taehee thought her a looney bin at first when he popped into the funeral parlor before she was done talking with a client, and saw her holding a corpse xD

 Miannag:

But I can't understand how was she taken back to work there after she flees from her job two years ago... who would accept her ?

I mean i don't disagree, but i think this is a mixture of dramalogic (tm) and the fact that funeral director as a job is a) not very popular in SK due to the social stigma the occupation brings with it (hands being "dirty" thru touching corpses, misfortune because they are surrounded by death) b) due to they most likely not overrun by job applications and it sorta is "take what ppl you can get." situation for the employer. Plus, she COULD reason that she was too shaken by the corpse of a child being her first job there to continue, that it was too great a shock or something, and we have got to know her team leader to be a pretty empathic, understanding guy. Thus why he gives her a second chance and maybe took her under his wings for the first times or so. (we only meet her when she is already working for nearly three months there after all) 

But mostly her return to the job is needed for the story to be able take place haha.

Thanks for your explanation bloomingtide.

I don't know how to quote you.

I really appreciate you typing this out! I've been catching up on this drama and while I'm enjoying it, the timeline had me confused, and I wasn't totally sure I was piecing it together right. Thanks again :)

Thank you for this. It told me instead of getting back to it I should rewatch the 6 episodes I have watched over again, or wait until it's completely finished.