The reality star and her husband Lamar Odom, who have not been pictured together since June, are expected to spend their big day apart.
Indeed, on the eve of their anniversary, Khloé posted a message on Instagram that perhaps reflects her inner turmoil.
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Taken from Alice in Wonderland, the text reads, " The Mad Hatter: 'Have I gone mad?
"Alice: 'I'm afraid so. You're entirely bonkers. But I'll tell you a secret. All the best people are'."
The post came hours after husband and wife reportedly held a short meeting at their Tarzana home, before the basketball player took off in his car for his downtown LA loft.
Despite their apparent difficulties, Lamar broke his silence this week to passionately defended Khloé and her family, calling them, "The ONLY ones that have been here consistently 4 me during this dark time."
He made his comments on Twitter after his father Joe Odom encouraged him to end his marriage amid reports of Lamar's substance abuse.
Keen to set the record straight, Lamar said his father hadn't called to check on him and stated that he had not been around to raise him. "He was absent ALL of my life due to his own demons," he wrote.
"My mother and grandmother raised me. Queens raised me. For the first time since they left, came a blessing of a FAMILY that I married into. FAMILY."
The sportsman went on to take full responsibility for his troubles, adding, "Only person 2 blame is myself. Say what you want about me but leave the ones who have done nothing but protect and love me out of this!"
A source close to the Kardashians said the family were deeply moved by Lamar's public tribute.
"It's always been nothing but love. They hope Lamar's finally on the right track," the insider said, adding that the acknowledgment of his problems is "promising news to the entire family".
Despite remaining resolutely silent on her marital problems, Khloé appears to be standing by her man.
Multiple sources have confirmed that husband and wife are in touch and dealing with various issues, including Lamar's addictions and his recent DUI charge.
And, perhaps most importantly, her wedding ring was still in place as she stepped out in Los Angeles this week.
"She still wants to save their marriage; she wants him to get better, but there is a lot to work out," a source confirmed to People.
"She's taking everything one day at a time and concentrating on herself. Everything with Lamar is very unclear."