Hey guys here's what's up. My phone escalation skills aren't the greatest, but I'm working on it, but I need some help with this.

Her: I'm off work sick at home with strep so your day was better than mine haha
Me: well if it makes you feel any better you have an adorable sicky face. (She sent me a pic)
Her: I have an adorable sicky face? Lol
Me: the pic you sent on saturday
Her: lol I know I just didn't think I looked adorable in it haha.

I'm drawing a blank on this. Most likely because I'm thinking too much, so any advice on how to escalate this convo is appreciated thanks!!

This is a type of talk bound to run into a brick wall. Because you give her a compliment but instead of acknowledging it she drives the conv. into no man's land. If you can't get the car to pick up from there she'll blame it on you. In her mind she will say that you are boring or don't know how to incite her, turn her on.

Even though she's really not helpful with making meaningful conversation.

What can you say at this point other than: "What can I do other than repeating what I just said? Maybe you're just fishing for compliments. That's cute but also kind of cheap. Then again since you're sick I'll cut you some slack and leave it at saying you're cute."

I kinda went that route the convo ended, so I'll just leave it at that, and start with a clean slate next time thanks for the advice I appreciate it!

You could just change the topic entirely.

Her: I have an adorable sicky face? Lol
Me: Holy fuck, I just saw Humphrey Bogart

Thanks mate I like that. When we're talking I'll usually throw something outta left field to keep it exciting, but I tried to keep this convo going too long without proper escalation, and it died out. So I'm gonna let it be a day or 2 then do what I usually do a high energy attention grabbing txt.

Yet. But. Given her lack of cooperation in convo 1 I doubt changing the topic to convo 2 will do much.

Both participants know the objective of the convo is not in the convo, but is mutual affirmation. After all.