How do I tell him? (Whitty x TaskForce!reader)

The Meeting (Part 1)

The day was new, the city waking up with adults heading to work either by walking or by car. You however were riding in a limo. Your co-worker, Gabriel Updyke, plans on hosting a large meeting today discussing our latest capture. You look over at another co-worker of yours, David and ask him.
"Hey David, what do you think about me getting a promotion?"

"You're lucky! Wish i caught them to get that promotion!"

"Heh, thanks David!"

The limo stops at the large, towering building. It had exactly 62 floors (you counted) and the meeting was on floor 60, only the most elite were allowed up there, which you were one of them. You and about 5 other people climbed into the elavator. There was David, Mary, Clyde, Rebecca and Jenna.

Clyde looked at his watch and showed everyone the time. He was always kind and caring, which was great for lurong out the targets. It was 7:54 am and the meeting was at 8:00 am. Can't this elevator go any faster? You're going to be late!

Finally the elevator stopped and you all scrambled into your seats. Updyke, your boss, was staring out of the window, his resting bitch face still appeared on his face. You weren't sure if it was natural face, considering he was a cloud, or if he could show any emotion at all.

Updyke:"Good job catching target 557... but we all know there is one who is at the top of our wanted list. You all know who he is, don't you?"

Whitmore...

Updyke:"He has been sighted near the night club 'Friday Night Funkin' on the opposite side of town lately. We presume he is stauing there for the time being. Everyone be on your guard and bring ALL of your equipment if you plan to go amywhere near there... understood?"

Everyone, including me, understood him. We knew the consequences if he was not appropriately apprehended.

~~~Time skip to tomorrow morning brought to you by midnight~~~

You were at the local walmart near your house, which you were examining apples for your next pie you were going to make, as you loved baking. You saw a man in a deep turqoise-green hoodie, his hood covering his face, and orange sweatpants speed walk to the register, only carrying basic foods like some fruit, vegetables and microwave meals.

You went to check out a few minutes later, having gotten all the groceries you needed. He was still there, looking at the self check-out in confusion. You went over to him and explained how it worked, he seems to appreciate it but only gave you a quiet "thank you". His voice was deep and scared, i hint of static in his voice was apparent as well. You shrugged it off and guessed it was his Species natural tone. After all you DID work for a cloud man.

As you finished you loocked back at him, he was fiddling around with a lot of one dollar bills, shakily. Did he not jave enough for the basic needs? You had to help. You walked over to him and slid your credit card througj the slot. He jumped as he heard the machine beep in approval.

"W-What did you do...?"

He asked in that same deep voice

"What do you mean? I paid for your stuff! You should probably go now, your making a line."

You informed him. You both looked back and before you knew it, he was sprinting for the door. He was strange but oh well, you helped someone and that was your good deed of the day.