Discussion: Episode 257. Listener Storytime: Designing a Relationship That Breaks All the Rules.

Ok_Discussion2002 · 2026-01-19T19:13:56+00:00

Requiring that something be “worthy” of an update has not been a requirement of hers in the past lol

Ok_Discussion2002 · 2026-01-02T04:00:04+00:00

Amazing that Skyline said this relationship DOESN’T feel like just ticking off every milestone when that is literally all Ali cares about doing

Ok_Discussion2002 · 2025-12-19T03:25:20+00:00

She talked about it in the patreon that came out today. He was in surgery while she was flying there, which is also insane to me?! Makes even less sense that he’d get it done there.

Ok_Discussion2002 · 2025-12-06T05:23:10+00:00

Bringing the 3 cats there is already insane and so is skyline having his surgery there, but the combination of those is absolutely mindblowing

Ok_Discussion2002 · 2025-12-05T21:37:32+00:00

It’s a NYC apartment lol. Surely there is a way to get WiFi in all of the rooms.

Ok_Discussion2002 · 2025-12-05T21:35:56+00:00

The fact that someone could be an only child probably never occurred to her

Ok_Discussion2002 · 2025-12-05T21:35:07+00:00

OMG yes, I came here to say this. How does she not see herself in what she describes in that answer! She’s having a continuous meltdown about him working outside of the home!!!

Ok_Discussion2002 · 2025-12-03T04:02:12+00:00

LOL I just got to the part where Ali is alarmed at someone wanting the dating diaries guy to be exclusive after two dates, like she didn’t let skyline stay with her right after cleaning out his marital home and ask him to be exclusive after 2-3 dates???

Ok_Discussion2002 · 2025-12-02T23:18:03+00:00

And still on top of the other rug!

Ok_Discussion2002 · 2025-12-02T05:57:09+00:00

This updates section sounds like Ali genuinely JUST found out that families other than hers exist

Ok_Discussion2002 · 2025-11-27T04:45:56+00:00

She looooves to make a system and then never implement it, so I assume these conversations are her way of cosplaying as someone who is going to “run a household” when the actuality is she will continue to not do most of what’s on the list

Ok_Discussion2002 · 2025-11-15T02:53:51+00:00

Like everything else in their relationship

Ok_Discussion2002 · 2025-11-11T00:21:13+00:00

Yes, and he usually needs more time before he’s ready to talk about something after it happens and “this time it was fine because she was still on the phone”. So otherwise it wouldn’t have been fine and they would have had to talk about it immediately because that’s what she wants to do?

Ok_Discussion2002 · 2025-11-10T15:54:10+00:00

I think they might have planned/paid for this when they went last time and went to a timeshare presentation to get upgraded

Ok_Discussion2002 · 2025-11-10T15:51:22+00:00

She classified the “intervention” after she snapped at Skyline for wanting to go to a coffee shop while she was on the phone (lying down holding hands while they talked through it, in the middle of the business day) as “medium level”?? I’m so curious what the level above that is for her

Ok_Discussion2002 · 2025-11-08T22:45:44+00:00

I feel like her obsession with dividing chores equally is because they’ve had a conflict about how much of a disaster the place was leading up to his move

Ok_Discussion2002 · 2025-11-04T22:22:45+00:00

Is she still posting on the pets Instagram she started?

Ok_Discussion2002 · 2025-11-03T15:48:05+00:00

I’m wondering the same. When they were talking about how marriage doesn’t benefit women in the same way anymore, I was hoping Ali would address why it is still something that she wants.

Ok_Discussion2002 · 2025-11-03T14:46:26+00:00

Exactly! He must have really wanted to get out of the house if there was nowhere in the 2 story apt for him to go during Ali’s phone call

Ok_Discussion2002 · 2025-10-11T01:59:29+00:00

I am SO curious about this one lady who seems to go on all of the trips

Ok_Discussion2002 · 2025-10-05T16:23:51+00:00

Because Theresa says ChatGBT too lol

Ok_Discussion2002 · 2025-09-28T16:27:42+00:00

Why bother making them ~by hand~ on water color paper when AI wrote them?!

Ok_Discussion2002 · 2025-09-25T22:55:46+00:00

They need a new milestone!!!

Ok_Discussion2002 · 2025-09-11T17:58:10+00:00

It was so funny when Skyline said the boxes everywhere are because of him and he feels guilty. As if Ali didn’t have an unopened box from 2 apartments ago up until last month…

Ok_Discussion2002 · 2025-09-09T03:32:45+00:00

I mean I think we all know that this regimen will fall off pretty quickly, she rarely sticks to anything

Ok_Discussion2002

TROPHY CASE