Jah Proposes to Winter Everett (Again) on The Family Chantel

Earlier this year, the trailer for The Family Chantel Season 3 promised a lot of drama.

It also promised some genuinely sweet moments for the family, despite their penchant for conflict and theatrics.

Winter and Jah have had major ups and downs, including Jah ruffling feathers with the titular family.

This week, Jah proposed to Winter a second time. It went much better than his first attempt.

On Monday night’s new episode, Jah took Winter Everett on an escape room date.

This kind of thing can make or break a relationship or even a friendship, depending upon how well people work together.

In his voiceover via the confessional camera, Jah made it very clear that he knows this.

“Being in an escape room, you know, two people trapped together,” Jah began.

“Two people that love each other trapped together,” he added.

“And,” Jah continued, “just trying to come out of it, I just think teamwork is what’s needed in everybody’s relationship and communication is key.”

“Proposing to Winter, last time it didn’t work,” Jay acknowledged.

He expressed: “this time I pray that everything works out perfectly as planned.”

An escape room can be a crucible for a relationship. With a proposal, the stakes are even higher.

For a while, Jah and Winter begin to work through the room’s puzzles.

Winter is, initially, treating it as any other outing with her boyfriend.

“Here I am on a date,” Winter described to the cameras, “this is something fun and new in our relationship.”

“He’s just been showing that he wants to be there for me,” Winter observed.

“It’s definitely really hard to move forward with Jah,” she admitted.

Winter added that the difficulty is apparent “just looking back at our history.”

“It’s a little difficult,” Winter admitted.

“But,” she emphasized, “I am choosing to just move forward.”

Winter affirmed: “Jah makes me happy and I just really want to have a happy and healthy relationship.”

The two solve the puzzle, opening the door and allowing them to leave.

But wait, there’s one more box — a red tool chest that is impossible to meet.

This isn’t a normal part of the room. This is Jah’s design.

“This is the moment of truth,” Jah said nervously.

He added: “I had them hide the ring inside the small red toolbox.”

“I just thought that was the perfect place to put that ring in that red box,” Jah explained.

Jay commented: “It was almost like a treasure box if you will.”

“Before we open this, I have something I wanted to say to you,” he told Winter.

Jay told his lady love that there was “something I need to tell you.”

Clearly sensing that Jah had something major on his mind, Winter replied: “Okay.”

Jah’s can’t miss proposal, which of course we included in this article’s video clip, includes a poem.

He reads it off of his phone, asking her if she will be his “wife-to-be.”

Jah slides the ring onto her finger — a simple gold band with a gorgeous black stone at its center.

“We’re engaged!” the two happily proclaim to the cameras.

They embrace, and Winter tells him that she loves the ring and how it makes her feel.

Word to the wise: be really, really sure of what you’re doing before you plan any kind of surprise proposal.

How cute the story would sound on Instagram does not matter as much as what your partner wants (unless maybe they’re an influencer).

There are very good odds that Winter knew or at least suspected that this was coming, which would be very smart on Jah’s part.

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