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If asked, Jack would tell you it was his idea to propose.
If he’s feeling sappy, he’d tell you he knew he’d one day marry Liz Lemon the second a piece of plaster fell on her head.
If he’s horny, he’d say it was the moment she made Josh do the worm in the middle of his contract negotiations.
If he’s looking for a fight, he’ll tell you it was the time he saw her angry badger face and realized she’s the only one who’s ever consistently beaten him. Every conversation is a negotiation after all, and she keeps winning if only due to sheer stubbornness and the constant weirdness that is her life.
If he’s feeling maudlin, he’d tell you that it was when he was in the hospital post-heart attack and realized that no one in his life would ever be there for him like her, that he knew he’d wait forever if she needed him to.
In reality, Jack never thought about it. Marriage was something he had already experienced and failed at. They’d even been married to each other for a short, disastrous time. Happy marriages were for other people, he’d decided a long time ago.
Him proposing was entirely Colleen’s fault actually. The year after his divorce from Avery had been rough. He didn’t understand Kabletown, his job was a dead-end, his sex life evaporated, and even negotiations failed to bring him any sort of joy.
Colleen invited herself to New York City for the Christmas holiday, apparently acting on an anonymous tip that he was depressed. “Imagine poor Liddy,” she told him, “no mother, father too busy being depressed to pay any attention to her.”
Jack rolled his eyes, gave some retort he was sure was exceedingly clever and would have gutted anyone other than Colleen, the heartless she-witch. But his heart wasn’t in it, and he had to quickly look away from his mother to avoid the sadness in her eyes.
“You should invite that Lemon over, I enjoy her.”
“Lemon…can’t.” The truth is, he had no idea what Lemon’s plans were. She’d broken up with Criss just three weeks prior, and had been acting funny ever since. It wasn’t like Floyd, she didn’t start crying and he hadn’t caught her eating ham in a wedding dress. She just seemed…distant. Every time he saw her she seemed to be deep in thought.
Jack didn’t know if he’d somehow upset her, so he hadn’t extended an invitation when his mother announced her intentions like he normally would. She had enough problems of her own right now that he didn’t need her to act as a buffer between him and Colleen.
Things were surprisingly okay in the days leading up to Christmas. The three Donaghys went to the park and to elite restaurants. He stood in hat shops and shoe shops and stared in shock and horror when Colleen revealed little Liddy dressed up exactly like her grandmother. They played board games and poker and, when they were too drunk to make any sense, with Liddy’s shape puzzles.
And then on Christmas Eve, the doorbell rang as Colleen was in the middle of stringing some popcorn for the tree.
“It’s already decorated mother, why on earth would we need popcorn garlands?” he yelled over his shoulder.
“Because it’s tradition.” She yelled back.
He didn’t bother hiding his smirk, instead turning forward and heading to the door.
Checking the peephole, no one was there. On guard, Jack grabbed the sword hidden in the coat stand and cracked open the door. Still nothing.
Jack was ready to head back inside, acutely aware of the cold snow swirling around his legs when he looked down and saw a box.
There was no address, just his name in large, familiar hand writing. “Jack Donaghy, open immediately.”
“Lemon, I know it’s you!” There was no answer. Maybe she’d sent Kenneth, but the page wouldn’t have left without trying to force Jack into a conversation.
In a second, the package was in his foyer and the door was firmly shut.
He carried it back to where Colleen now had at least five feet worth of strung popcorn on the ground by her feet, before gently opening the untapped box.
As he cleared the thick padding that lined it, Jack’s breath caught in his throat. In it, carefully wrapped in thick wool fabric and nestled in a mound of bubble-wrap, was a cookie jar.
Shaped like a teddy bear in a suit, the cookie jar stared up at Jack with a smile. He gently lifted it out of its packaging, trying to ignore the fluttering of his heart. He set it down on the coffee table, not even noticing Colleen get up and come over to investigate his gift.
Instead, he turned to the note that had been revealed when he moved the bear.
Dear Jack,
I know this has been a tough year for you, so- forgive the sentiment- hopefully this reminds you that not everything that is lost must be so forever. There is happiness everywhere, even if it’s just inside a cookie jar.
I’d say Happy Holidays, but I don’t want to hear that rant again, so instead, I hope you have a Merry Christmas and a Happy New Year.
Liz
P.S.- I hope you appreciate that I didn’t quote the Christmas Carol at all, even if you can be a real Ebenezer Scrooge. I can see you now, shaking your fist at the sky and shouting “Bah Humbug!”. Wait shit, I wasn’t supposed to quote it. Oh well, God bless us, Everyone!
Jack hears the faint scrap of porcelain on porcelain as Colleen lifts the teddy bear’s head to reveal a wide assortment of cookies.
“Marry her.” Colleen says decisively. “I’ve always liked her, and I’ve never been wrong about the women you’ve liked Jackie.”
“We’re just friends mother.”
“You can still be friends and be in love, Jack.”
He doesn’t bother denying he likes Lemon. Doesn’t hold her up against all the other women he’s dated or proposed to or married. He just exhales softly. “She just broke up with another man mother, she’s probably sworn off love entirely.”
“Oh Jackie,” she says, and Jack tries to think of any time his mother sounded as gentle as this. “Marry her. This is what love looks like.”
Six months later, after he got drunk and kissed her, and she got drunk and kissed him back, and they both panicked for two weeks before realizing they’ve been each other’s most important relationship for the past six years so fuck it let’s try this thing, he looks up from where he’s got Liz pinned against the kitchen island (it turns out most of her sex hang ups disappear once food gets involved, and that’s one weird sex thing he can get behind) and sees the cookie jar.
“Why’d you stop,” she complains, “I’m like already half naked and the granite is cold.”
Jack laughs brightly because of course Lemon complains even during sex and he can no longer imagine it any other way. “Nothing,” he tells her, before he returns to kissing her clavicle.
Three months after that, he pulls her aside after a successful show. He leads her out of 30 Rock and to her favorite hot dog stand. He waits until she’s got a mouthful of meat before he pulls a bulky object out of his bag.
He doesn’t bother kneeling, doesn’t make a fuss, just hands her a cookie jar shaped like a teddy bear in a Princess Leia costume.
“This is for you.” He says, as she finishes her hot dog and throws out the wrapper.
“Neat.” She gently opens the lid. “Oh.”
Jack tries not to panic. He tries to think of it as a negotiation, but he’s always failed at negotiating with Liz.
“Aren’t you supposed to like ask me or something?”
“I figured that’s what I was doing.”
“No I mean, aren’t you supposed to say ‘Liz Lemon, will you marry me?’”
“Well I would, but with your middle name would you want me to?” Jack grins as the badger face starts to appear, before slowly getting down on one knee. “Liz Lemon, will you marry me?”
“Again.”
“What?”
“Will you marry me again, Jack, we’ve been married before.”
Jack rolls his eyes, but she’s clearly enjoying this, so. “Alright. Elizabeth Miervaldis-“
“Hey!”
“Lemon, will you marry me again? This time for real.”
She grabs a cookie from the jar and chews on it thoughtfully. “Hey these are good.”
“Good God Lemon!”
“Alright, fine.” Her words aren’t particularly enthusiastic, but she’s grinning down at him and her eyes are sparkling and Jack gets what Colleen has always seen in Liz.
It takes them a year to get their schedules to work out right, but after wrapping the last day of TGS with Tracy Jordan, Liz and Jack get married. It’s an absolute disaster of course. Lutz managed to knock the cake over, Jenna got drunk and started singing, Tracy’s iguana escaped, and Frank managed to get locked in a supply closet completely naked.
In the end, Liz managed to wrangle her staff and Jack managed to prevent Jonathan’s attempts to stop the wedding.
It wasn’t perfect, but it was their day so it wouldn’t be right if it was.
Everyone agreed, however, that the food was excellent and Colleen Donaghy’s speech about acceptance and love and simple things and cookie jars was both sweet and incredibly weird- much like the couple before them.