This scenario is certainly one of the few most enigmatic, ambiguous, puzzling moments of this book. Dylan and his mother meet at the foot of the stairs (a reoccurring theme between the two in the book), and he makes a point of revealing a flask that he’d acquired of which she knew nothing about then shows her that he and Robyn barely drank any of the peppermint schnapps from it and most important of all, he emphasizes to her that she can trust him and reiterates this a second time.
How he words this seems important..
“I want you to know you can trust me and you can trust Robyn.
I had filled this so we could drink it tonight. I want you to see only a little tiny bit is missing.” “We had a little bit to drink at the beginning of the evening but no more after that. See? It’s close to the top.”
and a second time:
“I just wanted you to know you can trust me,” he said again.
He seems to underscore this.
Sue then goes on to ponder the private moment between herself and her son in the stillness of the night.
She wonders in retrospect that he may somehow had been mocking and tricking her and trying to prevent me from searching his room or was he seeking reassurance by trying to establish trust?
I have pondered about this quite a bit now and have examined both possibilities. So let’s take a look at this more closely.
Scenario 1) Dylan possibly mocking, openly deceiving and tricking his mom and trying to prevent her from searching his room:
* Eric spent the night over Dylan’s house the Friday night April 16th. Dylan’s parents report that Eric had a heavy black bag with him which they assumed was just computer equipment that the boys were hauling upstairs.
*Prom was on Saturday, April 17th. Dylan got home at 4 a.m. on April 18th and that is when the ‘Flask/Trust’ exchange occurred between the two.
*Sunday, April 18th – Dylan slept late, then left for Eric’s in the afternoon.
“He looked terribly tired, which was only to be expected after the sleepover on Friday night and a late night at the prom.” Dylan got home later and Sue and Tom ate dinner alone.
*Monday, April 19th – Dylan goes to school and Dylan’s mom drives 26 miles to her job to work for the day. When she gets home, Dylan tells her that he and Eric are going to Outback Steakhouse for dinner since he had coupons. Dylan gets home at 8:30 pm and goes to bed.
There is a 48 hour window of time from April 18th, when Dylan got home at 4 a.m. to call attention to his flask to when he rose at 4 a.m. on April 20th to bound down the stairs and sharply bark ‘bye’ to his mom, leaving his life forever behind.
In this time period, the window of opportunity for Dylan’s parents to be home while Dylan wasn’t was a very small window of time: 1) On Sunday afternoon to late evening and 2) Monday evening when Dylan elects to go out to dinner with Eric.
Realistically, did Dylan hypothetically need to call attention to his flask to reassure his mother that he was trustworthy in an attempt to thwart her from potentially searching his room in that very small window of time that he wasn’t home? To me this sounds just a bit far fetched. I mean, couldn’t he have just as easily not mentioned that he was concealing a flask and to not mention anything about drinking that evening? Then there would never have been any conversation to even plant any seeds of doubt in his mom’s mind as to whether she could trust him or not. If he said nothing at all, it would have not called attention to any sort of doubts for which she might feel obligated to search his room in the first place, right? Furthermore, if Dylan had done this for damage control, to prevent his mother from searching his room, what if that had backfired? What if his calling attention to his flask and whether she could trust him made Sue feel instead, highly suspicious enough to warrant searching his room because of the very weird thing he’d done? Doing such a thing as reassuring his mom she could trust him could’ve just as easily backfired against his supposed ulterior motive to prevent her from searching his room.
And, remember, Eric brought the bag over Dylan’s house on Friday, April 16th. So, what about the window of time that Dylan left to go to prom on the 17th? Wouldn’t Dylan’s parents have been traipsing in and out of Dylan’s room helping him get dressed and primped and ready for prom during the day of the 17th? How could Dylan have prevented them from entering his room? Not likely. In the evening from about 6 pm onward Dylan was out of the house enjoying the prom. Any chance his mom might have searched his room unawares then? If he was concerned then, why not bring up the flask diversion earlier on?
Doing what Dylan did was an out-on-a-limb risk if he were trying to manipulate his mom from prying in the last bit of time he had left at home. There wasn’t much time left there at home with his parents anyway even worth calling attention to himself and issues of trust, frankly. Even still, he only would’ve potentially deterred his mom. What about his dad?
If Dylan was trying to malicious mock his mother by being cocky waving the flask around and telling her with false sincerity that she could trust him, I tend to not think that he would not have said on the Basement Tapes “My parents have been good to me. I don’t want to browse there.” Because, there in the tapes, he had the open floor to be as cruel and mocking as possible about his parents.. and yet, yet..he refrained. In his Basement Tapes ‘goodbye’ 30 min before the massacre, Dylan addresses his goodbye to only his mom: “Hey mom. Gotta go. It’s about a half an hour before our little judgment day. I just wanted to apologize to you guys for any crap this might instigate as far as (inaudible) or something. Just know I’m going to a better place. I didn’t like life too much and I know I’ll be happy wherever the fuck I go. So I’m gone.”
Sue mentions: “He looks away from the camera, as if speaking only to himself. Then he says softly, “Just know I’m going to a better place. I didn’t like life too much….”
The other possibility that Sue considers as well…
Scenario 2) “I once shared these thoughts with a psychologist who then asked me, “How do you know he wasn’t in earnest? Maybe he did want to earn your approval, and it had nothing to do with what was to follow.” It’s one of the many things I will never know.”
The idea here is that Dylan, in having slightly nipped from his flask so he was a bit more communicable with his mom combined with the fact that he had an unexpectedly very good, memorable evening at prom with his friends, on a whim, decides to reveal the flask he had concealed on him and came clean with his mom that he had been drinking – but only just a bit. It would be his demonstration of proof to her that he was being her good, responsible son and that he, along with Robyn, were earnest and trustworthy people and that she did not have to worry about him or his conduct. That in that snapshot moment in time, he felt the strong need to earn his mother’s approval. In some ways it had nothing at all to do with the abomination he would be responsible for in less than 48 hours but in another way, it had everything to do with just that.
Perhaps Dylan in that snapshot moment of time, in this quiet pocket of a private moment with his mom on the landing of the steps, was a subconscious gesture demonstrating and proving in a odd off-beat way to her that he was, on that last good evening of his life, being her honorable, trustworthy, good son. His goodbye to his mom was said in as sort of between the lines context to her, by giving her a reassure of her faith and trust in her son and winning her approval one last time. This is what he could take with him to his death and this was the goodbye he would give to her. Like many of those that are suicidal and often before they take their life, Dylan is giving his parting gifts to everyone – little tokens of good memories to cherish for them (as much as for himself): to Robyn, he obliged being her date for prom, to Nate, he smoked a cigarette outside the restaurant at prom, standing alone with him, laughing and talking about their future plans and with Devon, he had the last slow dance and gave her a kiss on top of her head. It had been such a perfect night for Dylan; a perfect end to his beginning of his end.. And when he got home – there was his mom to meet him at the stairs – and so his gift in some bizarre fashion, became a simple reassure to underscore to her, if only for but a moment, that ‘I have been your good, responsible son. You see here what I have? I didn’t have to show you what I snuck into prom but I am.
I haven’t disappointed you ever, have I, mom? Trust me, mom. I’m leaving you with this memory…”
So… those are the two possible scenarios that Sue has provided in her book to which she mulls over along with the conclusions I tend to arrive at while thinking of those two separate motivating factors. In the end though, why Dylan did this is a mystery that he takes with him to his figurative grave. I wonder if he even fully knows why he did it. It seemed to have almost been impulsive as if a need on his part to do this with his mother to make himself right in her eyes. For me, this is one of the most, if not the most, enigmatic riddles about Dylan in his mother’s book. I have been puzzling over it ever since. Tbh, I read it the first time and went “wow, whoah.” Baffling. It is simply one of those unanswerable questions that make answers, answers that conceive questions and at long last he is content….
The Everlasting Contrast 
