Yesterday's gone. Tomorrow's not here.

[Flight]

I might have just tried:

YOU: Was just throwing away old pictures of you Hope you are doing well.. KIDDING! ... Real possible start: "Had a great time out at [her favorite dinner place] the other night, reminded me of that time [fill in the blank]. Hope you are doing well (you went there without her???)
HER: Hey...how are you??
YOU: Great! Always on the go. Getting ready to travel.
HER: Oh? Where?
YOU: Asia. GTG, Take care!

Just my critique, take it for what it's worth

ME (8:30PM): How goes? (you are expecting a response. She is now pressured to answer you. She may be thinking, "Ah, he is missing me and trying to feel me out)

HER (9:30 AM): Hey...how are you?? (not bad, maybe she cares, maybe she feels rude not responding)

ME(4:00 PM): I'm good, I'm good... just got told I have to go to Taiwan next month... ugh... anyway... I was just wondering how you are doing since we haven't talked in a while.

(TMI. not confident. Like Sean Connery in Hunt for Red October, make it "One Good Only..." He said "one ping only"... never mind Make her think you are doing great without her! Maybe change it to "Great!" or "Really good!". The second part is passive, "I have to go...". Take charge, you ARE GOING you are a businessman, you plan your life, you are no ones lacky!
She knows you haven't talked in a while. You don't miss her, you aren't tracking the time. Events reminded you of her and you were just wishing her well.

HER: UGH.... that stinks!!... i'm doing ok.

Anyway, it seemed like a decent interaction.