When exactly do Gordon's intentions in "The Gift" turn?

Question

When exactly do Gordon's intentions in The Gift turn into the desire to do harm to Simon?

I just watched this the other night, the timeline is a bit confused in my mind but...

Simon and his wife Robyn run into his old classmate Gordon.

Gordon starts sending them lots of gifts, showing up to their house uninvited, etc. He's coming off as kind of creepy at this point, but hasn't openly shown any bad intentions yet... has he? Can we assume he was making a legitimate attempt to be friends at this point? Or does the movie point to his bad intentions going back even to the start?

At one point he writes his name and number on a marker board on their fridge. During one of his visits he notices his name has been wiped out and replaced with "weirdo", a nickname Simon and other kids used to tease him with back in their school days. He is visibly upset and leaves.

After that point his motives have clearly changed to questionable (though you don't find out a lot of what he did until the end of the movie.) He invites Simon and Robyn to dinner in a house that it turns out isn't his, makes up a lie to get away from them to record how they talk when he isn't around. However, it's still not clear to me if he had anything harmful planned at this point, or was just kind of trying to dig a bit more to see how they really felt about him? While he is gone Simon says a lot of bad stuff about him, which, as he has recorded it, he obviously hears at some point.

After that party ends poorly with Simon telling him to no longer contact him or Robyn, Gordon (presumably) kills the fish he gave them as a present, and (probably?) kidnaps their dog though eventually lets it go unharmed. But he also eventually writes a letter saying that he is willing to let bygones be bygones. Is there any reason to believe that he is considering this at this point? Or was he already scheming?

Robyn gets pregnant somewhere in here. She also starts feeling like she is being stalked, is having trouble sleeping, goes on pills again.

So somewhere in here Simon hunts down Gordon to try to apologize, mostly just because Robyn wants him to. It doesn't go well. I'm a bit confused on the timeline here but Gordon essentially says it is too late, and you learn out later why... he has already put some really bad stuff in motion to harm Simon with. He's clearly committed to this plan at this point.

Anyway, Simon and Robin cut him out of their lives, months pass, everything seems ok until the baby is being born and things get really crazy and then we finally see what exactly Gordon did that was so bad. (I mean, it is purposely left open as to whether he did the REALLY BAD THING he teases Simon with or not, but even if not, he still did some pretty messed up stuff.)

I guess I'm just confused as to when exactly his intentions went from ok (were ever ok?) to questionable to actively scheming to do harm to Simon (with Robyn as the means.)

And there is one specific part of the video he sends to Simon at the end to taunt him with that I can't place on my timeline... a part that shows he is stalking Simon and Robyn and filming them outside of their home. When exactly he started doing this is probably a big clue as to when he crossed into really bad intentions, but I don't really know where it fits on the timeline.

Answer 1

In the Movie "The Gift" many stones have been left unturned, but basically the plot was that Gordon wanted to give the same pain to Simon which he had to bear whole of his life.

As in the Childhood Simon fabricated a story that Gordon was found in a car being molested by an old boy. Which destroyed his life and left a scar of pain and agony over his soul.

In order to give the same his first mission was to get a soft corner in Robyn's heart by showing his innocence. He chose a gift to be the best way to get near to her.

In the ending scene we get to see that:

Robyn gives birth to child and Simon goes home and finds gift box from Gordo, containing footage of Gordo molesting Robyn after she fainted in the house. The footage cuts out suddenly. Gordo visits Robyn in the hospital to congratulate her. Simon rushes to the hospital, where Gordo calls him, taunts him and refuses to say who the baby's father is.

So his refusal to say baby's father name did two things

1. Whenever Simon will look at the baby the question about father will kill him from inside and will remind him of Gordo.In the same way the wrong notion about Gordo was fed into the mind of other children about molestation.

2. The last visit to Robyn in the hospital and showing the scar given to him by Simon was intentional for breaking the last thread of relationship between couples in this way he just separated Simon from his family In the same way he had to face after Molestation issue.

So he took full revenge from Simon. Sp I think this will answer your question about the complete scenario.

Answer 2

ref : The Gift Explained

Simon, right from school, is a bully. He does whatever it takes to get him to a better spot in life. For all you know Simon coined the name “Gordo the Weirdo”. He creates a fake story about Gordo being molested by a senior student in a car. Gordo’s dad finds out about this and beats the crap out of Gordo to an inch of his life. Years pass, Gordo’s life has been in turmoil because of that incident while Simon has made it big.

Gordon is the loner he is today because of Simon. He's never been able to get over what happened to him. When he runs into Simon and Robyn in LA, in his head he's looking for a fresh start and perhaps an apology.

Simon doesn't care or feel sorry about what he did to Gordon.

While the movie doesn’t show it, Simon would have screwed around with a lot of kids and their lives. One such victim is Gordon.

Simon doesn't consider it even a remote possibility to be friends with Gordon because they never were and they can't be now all of a sudden.

Gordon may have had no bad intentions had he seen a changed Simon or got an apology. Neither of that happened. Simon is still the same old Pr*ck. And as rightly mentioned by @Andrew Whatever in the question, Simon still refers to him as Gordo the Weirdo and writes that on the fridge.

Gordon is not mentally stable or a righteous person either. Even before the dinner invitation, Gordon decides to break in to some random house. Only at dinner Simon says that need to stop meeting and that they were never friends. Gordon drags the otherwise innocent Robyn into his revenge.

So based on all of this, Gordon has always carried hatred for Simon all the years. Him running in to Simon in LA after all the years brings back all the hate. He (in his own twisted way) tried to be the better man by being friendly (which we define as creepy). Knowing that his friendliness is belittled by Simon (the "Gordo the Weirdo would be the final nail on the coffin), his intentions turn hostile.

Answer 3

My impression is that while he didn't necessarily ever have good intentions toward Robyn and Simon, he didn't hatch his ultimate plan until after Simon told him to leave them alone.

He had a key to their house which he had to have gotten during one of his visits to Robyn, and he had the recording of Simon making fun of him in the mansion while he was "out talking to his ex-wife" so he must've had a plan early on to at least gather personal information and details from them in case he wanted to exact some revenge or blackmail. But I think the actual plan of drugging and raping Robyn came later.